Pitchfork Music Festival

#2 Festival (up from #4)
The leading showcase of independent music got more international press in 2011 than ever before. Held in Union Park, the free-spirited, deliberately affordable Pitchfork Music Festival has three stages that showcase nearly 40 headline acts, including Beach House, Sleigh Bells, and Feist. Brands such as Heineken, Intel, Whole Foods, and VitaminWater are sponsors. Next: July 12-14, 2013
The leading showcase of independent music got more international press in 2011 than ever before. Held in Union Park, the free-spirited, deliberately affordable Pitchfork Music Festival has three stages that showcase nearly 40 headline acts, including Beach House, Sleigh Bells, and Feist. Brands such as Heineken, Intel, Whole Foods, and VitaminWater are sponsors. Next: July 12-14, 2013
Photo: Rebecca Smeyne
2. Chicago Air and Water Show

#3 Festival
The iconic local tradition—scored with the sounds of thrillingly loud engines—lures two million spectators to the lakefront. In the corporate hospitality area of the Chicago Air and Water Show, companies such as Shell and Boeing host parties. Next: August 18-19, 2012
The iconic local tradition—scored with the sounds of thrillingly loud engines—lures two million spectators to the lakefront. In the corporate hospitality area of the Chicago Air and Water Show, companies such as Shell and Boeing host parties. Next: August 18-19, 2012
Photo: Courtesy of City of Chicago
3. Chicago Blues Festival

#4 Festival (up from #5)
Chicago puts on the world’s largest free blues festival, which this year was headlined by Mavis Staples and drew 500,000 fans. Next: June 2013
Chicago puts on the world’s largest free blues festival, which this year was headlined by Mavis Staples and drew 500,000 fans. Next: June 2013
Photo: Courtesy of City of Chicago
4. Chicago Jazz Festival

#5 Festival (up from #6)
A Labor Day weekend tradition, the Chicago Jazz Festival has four stages with free performances from big-name artists such as Diane Reeves. Next: August 30-September 2, 2012
A Labor Day weekend tradition, the Chicago Jazz Festival has four stages with free performances from big-name artists such as Diane Reeves. Next: August 30-September 2, 2012
Photo: Courtesy of City of Chicago
5. Chicago Gourmet

#6 Festival (up from #9)
Though a relative newbie to the festival scene, Chicago Gourmet has quickly built a reputation the city’s most prestigious food and wine event, and now attracts crowds of 10,000-plus. (In 2008, its first year, the festival drew 6,000 guests.) Showcasing 100 high-end restaurants and hundreds of international vintners, breweries, and spirit makers, the gathering also offers celebrity chef cooking demos, book signings, and popular events such as the "Hamburger Hop." Next: September 28-30, 2012
Though a relative newbie to the festival scene, Chicago Gourmet has quickly built a reputation the city’s most prestigious food and wine event, and now attracts crowds of 10,000-plus. (In 2008, its first year, the festival drew 6,000 guests.) Showcasing 100 high-end restaurants and hundreds of international vintners, breweries, and spirit makers, the gathering also offers celebrity chef cooking demos, book signings, and popular events such as the "Hamburger Hop." Next: September 28-30, 2012
Photo: Courtesy of Chicago Gourmet
6. Taste of Chicago

#7 Festival
Chicago’s sprawling food festival, once the city’s most successful large-scale event, has been revamped to address declining attendance and profits in recent years. This year, the Illinois Restaurant Association managed Taste of Chicago, shortening it from 10 to five days, adding attractions such as pop-up restaurants, and inviting guests to purchase tickets to concerts by Jennifer Hudson. Some one million guests attended and many vendors reported increased profits. Next: July 2013
Chicago’s sprawling food festival, once the city’s most successful large-scale event, has been revamped to address declining attendance and profits in recent years. This year, the Illinois Restaurant Association managed Taste of Chicago, shortening it from 10 to five days, adding attractions such as pop-up restaurants, and inviting guests to purchase tickets to concerts by Jennifer Hudson. Some one million guests attended and many vendors reported increased profits. Next: July 2013
Photo: Courtesy of City of Chicago
7. Grant Park Music Festival

#8 Festival
The free, outdoor classical music festival celebrates its 50th anniversary this year, with a number of events that included a first-of-its-kind simulcast of the Paris Opera Ballet’s performance of Giselle from the Harris Theater on June 27. Next: June 13-August 18, 2012
The free, outdoor classical music festival celebrates its 50th anniversary this year, with a number of events that included a first-of-its-kind simulcast of the Paris Opera Ballet’s performance of Giselle from the Harris Theater on June 27. Next: June 13-August 18, 2012
Photo: Norman Timonera/Courtesy of Grant Park Music Festival
8. Chicago SummerDance

#10 Festival
Regarded as one of the largest outdoor dance-class series in the United States, Chicago SummerDance teaches an average of 1,200 participants per session. Participants get free classes in everything from swing to polka, then test their moves on an open-air dance floor with a live band. Next: July 19-September 16, 2012
Regarded as one of the largest outdoor dance-class series in the United States, Chicago SummerDance teaches an average of 1,200 participants per session. Participants get free classes in everything from swing to polka, then test their moves on an open-air dance floor with a live band. Next: July 19-September 16, 2012
Photo: Courtesy of City of Chicago/Department of Cultural Affairs and Special Event
9. Printers Row Lit Fest

#12 Festival
The Midwest’s largest free, outdoor literary event fills five city blocks with wares from some 200 booksellers and also has a poetry slam and book signings. This year, writers such as Sapphire and poet Mark Doty made appearances at the Printers Row Lit Fest. Next: June 2013
The Midwest’s largest free, outdoor literary event fills five city blocks with wares from some 200 booksellers and also has a poetry slam and book signings. This year, writers such as Sapphire and poet Mark Doty made appearances at the Printers Row Lit Fest. Next: June 2013
Photo: Glenn Kaupert Photography
1. NeoCon

#1 Art & Architecture Event (up from #2)
North America’s largest design exposition and conference for commercial interiors, NeoCon draws some 40,000 international industry pros, and inspires glitzy fund-raisers and swank showroom parties. Next: June 2013
North America’s largest design exposition and conference for commercial interiors, NeoCon draws some 40,000 international industry pros, and inspires glitzy fund-raisers and swank showroom parties. Next: June 2013
Photo: R25 Productions
2. SOFA

#2 Art & Architecture Event (up from #3)
A contemporary art and design fair, Sculptural Objects and Functional Art attracts 30,000 collectors to Navy Pier. Next: November 2-4, 2012
A contemporary art and design fair, Sculptural Objects and Functional Art attracts 30,000 collectors to Navy Pier. Next: November 2-4, 2012
Photo: Cheri Eisenberg
3. Diffa’s Dining by Design

#3 Art & Architecture Event (up from #4)
The stylish trend showcase enlists leading artists from a several genres to design dining-room vignettes. Proceeds from Dining by Design benefit the Design Industries Foundation Fighting AIDS. Next: November 1-3, 2012
The stylish trend showcase enlists leading artists from a several genres to design dining-room vignettes. Proceeds from Dining by Design benefit the Design Industries Foundation Fighting AIDS. Next: November 1-3, 2012
Photo: Amanda Fisher
4. Art Institute of Chicago’s Woman’s Board Gala

#4 Art & Architecture Event (new to the list)
The famous museum’s largest fund-raiser is held at a different time each year to correspond with a major exhibition. This year’s glitzy event celebrated pop artist Roy Lichtenstein and drew 1,100 guests between a gala dinner and an over-the-top new after-party hosted by local fashion icon Ikram Goldman. Next: June 2013
The famous museum’s largest fund-raiser is held at a different time each year to correspond with a major exhibition. This year’s glitzy event celebrated pop artist Roy Lichtenstein and drew 1,100 guests between a gala dinner and an over-the-top new after-party hosted by local fashion icon Ikram Goldman. Next: June 2013
Photo: Dan Rest
5. Museum of Contemporary Art’s ArtEdge

#5 Art & Architecture Event (new to the list)
The edgy museum’s big winter fund-raiser recently became annual due to popular request. The 2012 600-guest happening raised $1 million and had performances from George Clinton and Nick Cave’s sound suits as well as an appearance by Wolfgang Puck. Next: Spring 2013
The edgy museum’s big winter fund-raiser recently became annual due to popular request. The 2012 600-guest happening raised $1 million and had performances from George Clinton and Nick Cave’s sound suits as well as an appearance by Wolfgang Puck. Next: Spring 2013
Photo: James Prinz Photography/Courtesy of Nick Cave and the Jack Shainman Gallery, New York
6. American Institute of Architects’ Design Excellence Awards

#6 Art & Architecture Event
The event saw 285 submissions in 2011 and drew more than 800 industry pros. The American Institute of Architects’ Design Excellence Awards returns to Navy Pier this fall and will dole out awards in categories such as sustainability and interior architecture. Next: October 26, 2012
The event saw 285 submissions in 2011 and drew more than 800 industry pros. The American Institute of Architects’ Design Excellence Awards returns to Navy Pier this fall and will dole out awards in categories such as sustainability and interior architecture. Next: October 26, 2012
Photo: Connor Steinkamp/Steinkamp Photography
7. U.S. Green Building Council–Illinois Chapter's Limelight

#7 Art & Architecture Event
The gala hosted by the U.S. Green Building Council-Illinois Chapter honors eco-minded business leaders, government officials, and building practitioners. At this year's Limelight event, the organization gave Emerald Awards to companies including Testa Produce and BP Brightlights. Next: Spring 2013
The gala hosted by the U.S. Green Building Council-Illinois Chapter honors eco-minded business leaders, government officials, and building practitioners. At this year's Limelight event, the organization gave Emerald Awards to companies including Testa Produce and BP Brightlights. Next: Spring 2013
Photo: The Chapter
8. International Interior Design Association Black Tie Celebration

#8 Art & Architecture Event
The high-end celebration takes place during NeoCon, drawing 500 designers and manufactures to mingle and connect. The International Interior Design Association Black Tie Celebration includes cocktails, dinner, and dancing. Next: June 2013
The high-end celebration takes place during NeoCon, drawing 500 designers and manufactures to mingle and connect. The International Interior Design Association Black Tie Celebration includes cocktails, dinner, and dancing. Next: June 2013
Photo: IIDA
1. Bank of America Chicago Marathon

#1 Sports Event
One of the world’s largest big-city road races, the Chicago marathon sold out in a record six days for its 2012 iteration and has 45,000 registrants. Next: October 7, 2012
One of the world’s largest big-city road races, the Chicago marathon sold out in a record six days for its 2012 iteration and has 45,000 registrants. Next: October 7, 2012
Photo: Courtesy of Bank of America Chicago Marathon
2. Arlington Million

#2 Sports Event
The prestigious horse race—reportedly the world’s first to offer a million-dollar purse—lures 32,000 international guests and is broadcast on national TV. Next: August 18, 2012
The prestigious horse race—reportedly the world’s first to offer a million-dollar purse—lures 32,000 international guests and is broadcast on national TV. Next: August 18, 2012
Photo: Courtesy of Arlington Park
3. Bank of America Shamrock Shuffle

#3 Sports Event (new to the list)
The world’s largest timed 8K road race drew a record-breaking 34,372 runners this year. Next: March 2013
The world’s largest timed 8K road race drew a record-breaking 34,372 runners this year. Next: March 2013
Photo: Courtesy of Bank of America Shamrock Shuffle 8K
4. Bike the Drive

#4 Sports Event
Presented by MB Financial Bank, the springtime happening sees 20,000 cyclists pedaling down a car-free stretch Lake Shore Drive and ends with a giant pancake breakfast. The Bike the Drive race was extended by 30 minutes this year. Next: May 2013
Presented by MB Financial Bank, the springtime happening sees 20,000 cyclists pedaling down a car-free stretch Lake Shore Drive and ends with a giant pancake breakfast. The Bike the Drive race was extended by 30 minutes this year. Next: May 2013
Photo: Courtesy of City of Chicago
5. Chicago Triathlon

#5 Sports Event (new to the list)
Billed as the world's largest, the Chicago Triathlon has more than 11,000 participants, 250,000 spectators, and sponsors such as Toyota and Cliff Bar. Next: August 24-26, 2012
Billed as the world's largest, the Chicago Triathlon has more than 11,000 participants, 250,000 spectators, and sponsors such as Toyota and Cliff Bar. Next: August 24-26, 2012
Photo: EricWynn.org
6. Susan G. Komen Race for the Cure

#6 Sports Event
The race, which benefits breast cancer research, draws 10,000 runners to Grant Park and has a suburban sister race in Lombard the following day. National sponsors for the Susan G. Komen Race for the Cure in Chicago include Ford and Yoplait. Next: September 22, 2012
The race, which benefits breast cancer research, draws 10,000 runners to Grant Park and has a suburban sister race in Lombard the following day. National sponsors for the Susan G. Komen Race for the Cure in Chicago include Ford and Yoplait. Next: September 22, 2012
Photo: Modern Image Studios
7. L.A.T.E. Ride

#7 Sports Event (new to the list)
Presented by Sports Authority, Peoples Gas, and North Shore Gas, the L.A.T.E. Ride is the largest nighttime biking event in Chicago and one of the largest cycling events in the world. Described as "Woodstock on Wheels," the unusual and beloved local tradition whisks 8,000 national cyclists on a 25-mile path through the city. Next: Summer 2013
Presented by Sports Authority, Peoples Gas, and North Shore Gas, the L.A.T.E. Ride is the largest nighttime biking event in Chicago and one of the largest cycling events in the world. Described as "Woodstock on Wheels," the unusual and beloved local tradition whisks 8,000 national cyclists on a 25-mile path through the city. Next: Summer 2013
Photo: Sebastian Kowalski
8. AIDS Walk & Run Chicago

#8 Sports Event
Organizers expect 7,000 participants at this year's AIDS Walk & Run Chicago. The moving race has a new "Memory Lane" with photos and tributes of runners’ loved ones. Next: September 30, 2012
Organizers expect 7,000 participants at this year's AIDS Walk & Run Chicago. The moving race has a new "Memory Lane" with photos and tributes of runners’ loved ones. Next: September 30, 2012
Photo: Ed Negron
9. Law Enforcement Torch Run’s Polar Plunge

#9 Sports Event
The Geico-sponsored Law Enforcement Torch Run’s Polar Plunge benefits the Special Olympics, drawing 6,290 plungers and raising $1.5 million this year. Next: February-March 2013
The Geico-sponsored Law Enforcement Torch Run’s Polar Plunge benefits the Special Olympics, drawing 6,290 plungers and raising $1.5 million this year. Next: February-March 2013
Photo: Courtesy of Special Olympics Illinois
10. Pets Are Worth Saving’s Run for Their Lives

#10 Sports Event
One of Chicago’s largest pet-friendly affairs, Pets Are Worth Saving’s Run for Their Lives draws 3,500 participants—many with their four-legged friends. Sponsors have included Subaru and American Airlines. Next: September 23, 2012
One of Chicago’s largest pet-friendly affairs, Pets Are Worth Saving’s Run for Their Lives draws 3,500 participants—many with their four-legged friends. Sponsors have included Subaru and American Airlines. Next: September 23, 2012
Photo: Monaghan Photography
11. Race to Mackinac

#11 Sports Event
Presented by Veuve Clicquot, the ritzy event sees nearly 350 boats race 333 miles to Mackinac Island. The Race to Mackinac is the longest annual freshwater race in the world. Next: July 2013
Presented by Veuve Clicquot, the ritzy event sees nearly 350 boats race 333 miles to Mackinac Island. The Race to Mackinac is the longest annual freshwater race in the world. Next: July 2013
Photo: Michele Idstein
1. Bud Billiken Parade and Picnic

#1 Parade & Holiday Event
With 1.8 million spectators and 80,000 participants, the Bud Billiken Parade and Picnic is the country’s largest African-American parade and the second largest annual parade in the nation. Next: August 11, 2012
With 1.8 million spectators and 80,000 participants, the Bud Billiken Parade and Picnic is the country’s largest African-American parade and the second largest annual parade in the nation. Next: August 11, 2012
Photo: Courtesy of Chicago Defender
2. Magnificent Mile Lights Festival

#2 Parade & Holiday Event
With Minnie and Mickey Mouse as grand marshals, the festive Magnificent Mile Lights Festival lures one million locals and tourists with floats, fireworks, celebrities, and a processional lighting of 200 trees to signal the start of the holiday season. Next: November 17, 2012
With Minnie and Mickey Mouse as grand marshals, the festive Magnificent Mile Lights Festival lures one million locals and tourists with floats, fireworks, celebrities, and a processional lighting of 200 trees to signal the start of the holiday season. Next: November 17, 2012
Photo: David Harrison Dion
3. Gay & Lesbian Pride Parade

#3 Parade & Holiday Event (up from #5)
The rainbow-hued event has seen attendance more than double in the past three years; now, it attracts an average of 800,000 spectators. This year, organizers of the Gay & Lesbian Pride Parade avoided congestion with a newly lengthened route. Next: June 2013
The rainbow-hued event has seen attendance more than double in the past three years; now, it attracts an average of 800,000 spectators. This year, organizers of the Gay & Lesbian Pride Parade avoided congestion with a newly lengthened route. Next: June 2013
Photo: Susan Mattes
4. McDonald’s Thanksgiving Parade

#4 Parade & Holiday Event
The city’s biggest parade to fall on a holiday is the nationally telecast McDonald’s Thanksgiving Parade, which draws 400,000 spectators. Next: November 22, 2012
The city’s biggest parade to fall on a holiday is the nationally telecast McDonald’s Thanksgiving Parade, which draws 400,000 spectators. Next: November 22, 2012
Photo: Courtesy of the McDonald’s Thanksgiving Parade
5. Christkindlmarket

#5 Parade & Holiday Event (new to the list)
A German-style holiday market in Daley Plaza, Christkindlmarket is a popular tradition that draws half a million visitors. Vendors sell hot spiced wine in collectible boot mugs, which are emblematic of the event. Next: November 21-December 24, 2012
A German-style holiday market in Daley Plaza, Christkindlmarket is a popular tradition that draws half a million visitors. Vendors sell hot spiced wine in collectible boot mugs, which are emblematic of the event. Next: November 21-December 24, 2012
Photo: Timmy Samuel/Courtesy of the Christkindlmarket
6. 26th Street Mexican Independence Day Parade

#7 Parade & Holiday Event
A lively celebration of Mexican culture, the 26th Street Mexican Independence Day Parade draws 500,000 spectators and takes place every September. Next: September 9, 2012
A lively celebration of Mexican culture, the 26th Street Mexican Independence Day Parade draws 500,000 spectators and takes place every September. Next: September 9, 2012
Photo: Marco Flores
7. Memorial Day Parade

#9 Parade & Holiday Event
One of the nation’s largest holiday parades, the Memorial Day Parade saw C.I.A. director David Petraeus as grand marshal in 2012. Next: May 27, 2013
One of the nation’s largest holiday parades, the Memorial Day Parade saw C.I.A. director David Petraeus as grand marshal in 2012. Next: May 27, 2013
Photo: Courtesy of City of Chicago
8. Chicagoland Toys for Tots Motorcycle Parade

#11 Parade & Holiday Event
The warm-hearted Chicagoland Toys for Tots Motorcycle Parade sees more than 8,000 motorcyclists collecting donations for underprivileged children. Next: December 2, 2012
The warm-hearted Chicagoland Toys for Tots Motorcycle Parade sees more than 8,000 motorcyclists collecting donations for underprivileged children. Next: December 2, 2012
Photo: Jack Voss
9. Eve of the Eve

#12 Parade & Holiday Event
The massive party draws 2,0000 revelers to Union Station for an early New Year’s Eve celebration benefiting Hindsight. Next: December 30, 2012
The massive party draws 2,0000 revelers to Union Station for an early New Year’s Eve celebration benefiting Hindsight. Next: December 30, 2012
Photo: Courtesy of Spectaculights
10. AIDS Foundation of Chicago’s World of Chocolate

#13 Parade & Holiday Event
A holiday fund-raiser that draws 1,500 guests and offers lavish chocolate treats from 30 confectioners, the AIDS Foundation of Chicago’s World of Chocolate takes place at the Hilton Chicago each year. Next: November 29, 2012
A holiday fund-raiser that draws 1,500 guests and offers lavish chocolate treats from 30 confectioners, the AIDS Foundation of Chicago’s World of Chocolate takes place at the Hilton Chicago each year. Next: November 29, 2012
Photo: Courtesy of AIDS Foundation of Chicago
1. Chicago Auto Show

#1 Trade Show & Convention
The largest and longest-running auto show in North America has 1.3 million square feet of exhibits. Next: February 9-18, 2013
The largest and longest-running auto show in North America has 1.3 million square feet of exhibits. Next: February 9-18, 2013
Photo: Courtesy of Chicago Auto Show
2. National Restaurant Association Restaurant, Hotel-Motel Show

#2 Trade Show & Convention
Colocated with the International Wine, Spirits, and Beer event, the National Restaurant Association Restaurant, Hotel-Motel Show had more than 1,800 exhibitors and a keynote address from Bill Clinton in 2012. Next: May 18-21, 2013
Colocated with the International Wine, Spirits, and Beer event, the National Restaurant Association Restaurant, Hotel-Motel Show had more than 1,800 exhibitors and a keynote address from Bill Clinton in 2012. Next: May 18-21, 2013
Photo: Courtesy of National Restaurant Association
3. International Home and Housewares Show

#3 Trade Show & Convention (up from #4)
With several celebrity chefs in attendance and an extended four-day run, this year's International Home and Housewares Show drew 60,000 buyers and 2,100 exhibitors. Next: March 2-5, 2013
With several celebrity chefs in attendance and an extended four-day run, this year's International Home and Housewares Show drew 60,000 buyers and 2,100 exhibitors. Next: March 2-5, 2013
Photo: Courtesy of International Housewares Association
4. Radiological Society of North America Scientific Assembly and Annual Meeting

#4 Trade Show & Convention
The scientific event, held at McCormick Place each November, has nearly 700 exhibitors and 60,000 international attendees. Next: November 25-30, 2012
The scientific event, held at McCormick Place each November, has nearly 700 exhibitors and 60,000 international attendees. Next: November 25-30, 2012
Photo: RSNA
5. America’s Beauty Show

#5 Trade Show & Convention (up from #6)
This year the beauty-focused show drew 50,000 industry pros and included appearances by industry stars like Tabatha Coffey. Next: March 9-11, 2013
This year the beauty-focused show drew 50,000 industry pros and included appearances by industry stars like Tabatha Coffey. Next: March 9-11, 2013
Photo: BABAK for 2012 America's Beauty Show
6. Chicago Comic and Entertainment Expo

#6 Trade Show & Convention (new to the list)
In its first year, 2010, the Chicago Comic and Entertainment Expo had 27,500 attendees; 34,000 people made it out in 2011, and this year’s attendance soared to 41,000. Next: April 26-28, 2013
In its first year, 2010, the Chicago Comic and Entertainment Expo had 27,500 attendees; 34,000 people made it out in 2011, and this year’s attendance soared to 41,000. Next: April 26-28, 2013
Photo: Courtesy of the Chicago Comic & Entertainment Expo
7. Sweets & Snacks Expo

#7 Trade Show & Convention
Covered by consumer and industry publications alike, the Sweets & Snacks Expo shows signs of continued growth, with 570 booths and 15,000 guests this year. Next: May 21-23, 2013
Covered by consumer and industry publications alike, the Sweets & Snacks Expo shows signs of continued growth, with 570 booths and 15,000 guests this year. Next: May 21-23, 2013
Photo: Courtesy of Jelly Belly Candy Company
8. Graph Expo

#8 Trade Show & Convention
The Americas’ largest exhibition and conference for the graphic communications industry drew 20,450 attendees in 2011. Next: October 7-10, 2012
The Americas’ largest exhibition and conference for the graphic communications industry drew 20,450 attendees in 2011. Next: October 7-10, 2012
Photo: Courtesy of Graph Expo
9. Chicago Boat, Sports & RV Show

#9 Trade Show & Convention
The Midwest’s largest show of its kind, Chicago Boat, Sports & RV Show, drew 35,400 attendees and was sponsored by Progressive insurance this year. Attractions included scuba demos and a catch-and-release trout pond for kids. Next: January 9-13, 2013
The Midwest’s largest show of its kind, Chicago Boat, Sports & RV Show, drew 35,400 attendees and was sponsored by Progressive insurance this year. Attractions included scuba demos and a catch-and-release trout pond for kids. Next: January 9-13, 2013
Photo: Courtesy of the Chicago Boat, Sports & RV Show
1. Chicago Symphony Orchestra Symphony Ball

#1 Theater, Dance & Music Event
The premiere autumn event has featured performances from the likes of Lang Lang and Renee Fleming; it draws major corporate sponsors and typically raises more than $1 million. Next: September 29, 2012
The premiere autumn event has featured performances from the likes of Lang Lang and Renee Fleming; it draws major corporate sponsors and typically raises more than $1 million. Next: September 29, 2012
Photo: Todd Rosenberg Photography
2. Lyric Opera’s Opening Night Gala Benefit and Opera Ball

#2 Theater, Dance, & Music Event
The eight-hour affair emanates a grand sense of occasion with red-carpet arrivals, a bugle-scored grand march, and opera stars. This year the Lyric Opera’s opening night gala benefit and Opera Ball includes a performance of Richard Strauss’s Elektra. Next: October 6, 2012
The eight-hour affair emanates a grand sense of occasion with red-carpet arrivals, a bugle-scored grand march, and opera stars. This year the Lyric Opera’s opening night gala benefit and Opera Ball includes a performance of Richard Strauss’s Elektra. Next: October 6, 2012
Photo: Cheri Eisenberg
3. Steppenwolf Theatre Gala

#3 Theater, Dance, & Music Event
The prestigious gala has a successful live auction with unique packages donated by its high-profile company actors, who also attend. Next: Spring 2013
The prestigious gala has a successful live auction with unique packages donated by its high-profile company actors, who also attend. Next: Spring 2013
Photo: Joan Hackett
4. Joffrey Ballet Spring Gala

#4 Theater, Dance, & Music Event
This year, the dance lovers’ evening was attended by 800 guests including big-name business leaders and Mayor Rahm Emanuel. The 2012 spring gala raised $1.2 million and celebrated the women’s board’s 10th anniversary. Next: Spring 2013
This year, the dance lovers’ evening was attended by 800 guests including big-name business leaders and Mayor Rahm Emanuel. The 2012 spring gala raised $1.2 million and celebrated the women’s board’s 10th anniversary. Next: Spring 2013
Photo: Bob Carl
5. Goodman Theatre Gala

#5 Theater, Dance, & Music Event
With opulent decor evocative of the Moulin Rouge, the Goodman Theatre gala offered a cabaret-style performance from Tony award winner Laura Benanti and raised $800,000. Next: Spring 2013
With opulent decor evocative of the Moulin Rouge, the Goodman Theatre gala offered a cabaret-style performance from Tony award winner Laura Benanti and raised $800,000. Next: Spring 2013
Photo: Violet Dominck
6. TBS Just for Laughs Festival

#6 Theater, Dance, & Music Event
With stand-up comedy, sketch shows, and films in venues across the city, the TBS Just for Laughs Festival has been a popular, quick-to-sell-tickets summertime tradition since launching in Chicago in 2008. This year’s talent included Vince Vaughn, Sarah Silverman, and Aziz Ansari. Next: June 12-17, 2013
With stand-up comedy, sketch shows, and films in venues across the city, the TBS Just for Laughs Festival has been a popular, quick-to-sell-tickets summertime tradition since launching in Chicago in 2008. This year’s talent included Vince Vaughn, Sarah Silverman, and Aziz Ansari. Next: June 12-17, 2013
Photo: Courtesy of TBS Just for Laughs Chicago
7. Ravinia Festival Gala

#7 Theater, Dance, & Music Event
The summertime fund-raiser celebrated the 50th anniversary of the women’s board this year with a performance from Patti Lupone and Patricia Racette. Next: July 2013
The summertime fund-raiser celebrated the 50th anniversary of the women’s board this year with a performance from Patti Lupone and Patricia Racette. Next: July 2013
Photo: Patrick Gipson/Ravinia Festival
8. Chicago Dancing Festival

#8 Theater, Dance, & Music Event (new to the list)
Now in its sixth year, the Chicago Dancing Festival has evolved from a one-day event into six days of free programming. The festival added the 3,800-seat Auditorium Theater to its slate of venues in 2011 and filled the space to capacity. Next: August 20-25, 2012
Now in its sixth year, the Chicago Dancing Festival has evolved from a one-day event into six days of free programming. The festival added the 3,800-seat Auditorium Theater to its slate of venues in 2011 and filled the space to capacity. Next: August 20-25, 2012
Photo: Cheryl Mann
9. Chicago Shakespeare Theater Gala

#9 Theater, Dance, & Music Event (new to the list)
The high-profile event has a host committee with representation from McDonald’s, ITW, and CME Group. The Chicago Shakespeare Theater Gala raises more than $1 million each year. Next: June 2013
The high-profile event has a host committee with representation from McDonald’s, ITW, and CME Group. The Chicago Shakespeare Theater Gala raises more than $1 million each year. Next: June 2013
Photo: Michael Litchfield
10. Hubbard Street Dance Company’s Spotlight Ball

#10 Theater, Dance, & Music Event
The gala includes dance performances and publicly acknowledges corporate support; this year, Northern Trust was honored. Next: Spring 2013
The gala includes dance performances and publicly acknowledges corporate support; this year, Northern Trust was honored. Next: Spring 2013
Photo: Robert Carl/Courtesy of Hubbard Street Dance Chicago
11. League of Chicago Theatres Gala

#11 Theater, Dance, & Music Event
The gala, which is considered a prime industry networking opportunity, honored Nathan Lane and Brian Dennehy this year and raised funds for 200 area companies. Next: Spring 2013
The gala, which is considered a prime industry networking opportunity, honored Nathan Lane and Brian Dennehy this year and raised funds for 200 area companies. Next: Spring 2013
Photo: Kimmy Noonen Photography
12. Lookingglass Theatre Company’s Gglassquerade

#12 Theater, Dance, & Music Event
The gala increased its ticket price this year and raised $600,000—up 10 percent from 2011. Actors in attendance included John Mahoney and David Schwimmer. Next: March 2013
The gala increased its ticket price this year and raised $600,000—up 10 percent from 2011. Actors in attendance included John Mahoney and David Schwimmer. Next: March 2013
Photo: Robert Carl
13. Redmoon Theater’s Spectacle Lunatique

#13 Theater, Dance, & Music Event
The gala draws attention for imaginative site-specific performances using pageants, puppets, and more. Next: March 2013
The gala draws attention for imaginative site-specific performances using pageants, puppets, and more. Next: March 2013
Photo: Christina Noel Photography
14. About Face Theatre’s Wonka Ball

#14 Theater, Dance, & Music Event
The event raises funds for the company for LGBT youth; it draws 600 guests and gets an over-the-top theme each year. Next: Spring 2013
The event raises funds for the company for LGBT youth; it draws 600 guests and gets an over-the-top theme each year. Next: Spring 2013
Photo: Kat Fitzgerald
1. American Cancer Society Discovery Ball

#1 Benefit (up from #3)
This year, the annual Discovery Ball served as a model for the society’s nationwide events and staffers from six major markets got "backstage training" at the illustrious affair. The benefit, which took over the Radisson Blu Aqua Hotel, raised a record-breaking $2.7 million, with a single auction lot bringing in an impressive $218,000. Next: April 27, 2013
This year, the annual Discovery Ball served as a model for the society’s nationwide events and staffers from six major markets got "backstage training" at the illustrious affair. The benefit, which took over the Radisson Blu Aqua Hotel, raised a record-breaking $2.7 million, with a single auction lot bringing in an impressive $218,000. Next: April 27, 2013
Photo: George Burns Photography Inc.
2. Chicago Urban League Golden Fellowship Dinner

#3 Benefit (up from #5)
Last year, comedian Steve Harvey served as the M.C. for the Chicago Urban League Golden Fellowship Dinner, which included a performance by Patti Labelle. The event raised $1.9 million and attracted 1,800 guests. Next: November 10, 2012
Last year, comedian Steve Harvey served as the M.C. for the Chicago Urban League Golden Fellowship Dinner, which included a performance by Patti Labelle. The event raised $1.9 million and attracted 1,800 guests. Next: November 10, 2012
Photo: Victor Powell Photography
3. Museum of Science and Industry’s Columbian Ball

#4 Benefit (up from #16)
The stylish evening raised nearly $2 million, drew politicians and corporate titans, and served an innovative dinner that included smoking cold soup and appetizers growing from beds of wheat grass. Next: October 20, 2012
The stylish evening raised nearly $2 million, drew politicians and corporate titans, and served an innovative dinner that included smoking cold soup and appetizers growing from beds of wheat grass. Next: October 20, 2012
Photo: J.B. Spector/Museum of Science and Industry Chicago
4. Chicago Public Library Foundation’s Carl Sandburg Literary Awards Dinner

#5 Benefit (up from #6)
Last year, the Chicago Public Library Foundation’s Carl Sandburg Literary Awards Dinner saw authors seated at every table, a record $1.25 million funds raised, and iconic film critic Roger Ebert honored. This year’s event will honor Don DeLillo and Walter Isaacson. Next: October 17, 2012
Last year, the Chicago Public Library Foundation’s Carl Sandburg Literary Awards Dinner saw authors seated at every table, a record $1.25 million funds raised, and iconic film critic Roger Ebert honored. This year’s event will honor Don DeLillo and Walter Isaacson. Next: October 17, 2012
Photo: Dan Rest
5. Advocate Christ Medical Center’s Salute Gala

#6 Benefit (up from #13)
The gala has grown rapidly in the past few years; this year, some 1,050 guests helped raise $1.5 million. The Advocate Christ Medical Center’s Salute Gala had a Mission Impossible-inspired motif. Next: Spring 2013
The gala has grown rapidly in the past few years; this year, some 1,050 guests helped raise $1.5 million. The Advocate Christ Medical Center’s Salute Gala had a Mission Impossible-inspired motif. Next: Spring 2013
Photo: Jeff Shear
6. Shedd Aquarium Gala

#7 Benefit (up from #8)
The popular black-tie affair includes an aquatic show, an elegant dinner, and an after-party with a chocolate buffet, lavish specialty cocktails, and dancing in a tented area overlooking the lakes and the city’s fireworks show. ITW and McDonald’s are among the many corporate supporters. Next: Summer 2013
The popular black-tie affair includes an aquatic show, an elegant dinner, and an after-party with a chocolate buffet, lavish specialty cocktails, and dancing in a tented area overlooking the lakes and the city’s fireworks show. ITW and McDonald’s are among the many corporate supporters. Next: Summer 2013
Photo: Courtesy of John G. Shedd Aquarium
7. Peggy Notebaert Nature Museum’s Butterfly Ball

#8 Benefit (up from #23)
With a bicycle theme that translated into tire chandeliers, the popular eco-friendly event raised $1.6 million and drew 620 corporate and civic leaders. Next: Spring 2013
With a bicycle theme that translated into tire chandeliers, the popular eco-friendly event raised $1.6 million and drew 620 corporate and civic leaders. Next: Spring 2013
Photo: Steve Becker Photography
8. Field Museum Gala

#9 Benefit (up from #17)
Always an ornate affair with a well-heeled crowd, the Field Museum Gala raised $1.3 million in 2011 and drew 700 guests. This year’s event will have a decadent Maharaja theme. Next: October 13, 2012
Always an ornate affair with a well-heeled crowd, the Field Museum Gala raised $1.3 million in 2011 and drew 700 guests. This year’s event will have a decadent Maharaja theme. Next: October 13, 2012
Photo: Cheri Eisenberg
9. Lincoln Park Zoo Ball

#10 Benefit
The ball had a "Great Cats-by" theme with a look evocative of an old-fashioned mansion. The Village People performed in a surprise cameo and more than 1,000 guests contributed to a fund-raising take of more than $1 million. Next: July 2013
The ball had a "Great Cats-by" theme with a look evocative of an old-fashioned mansion. The Village People performed in a surprise cameo and more than 1,000 guests contributed to a fund-raising take of more than $1 million. Next: July 2013
Photo: Alain Milotti
10. Make-A-Wish Foundation’s Wish Ball

#11 Benefit
The event raises more than $1 million annually, features celebrity guests, and has a long list of corporate supporters. David Spade and Billy Bush appeared at the Make-A-Wish Foundation’s 2012 Wish Ball. Next: Spring 2013
The event raises more than $1 million annually, features celebrity guests, and has a long list of corporate supporters. David Spade and Billy Bush appeared at the Make-A-Wish Foundation’s 2012 Wish Ball. Next: Spring 2013
Photo: Mary Melka
11. Ronald McDonald House Charities of Chicagoland and Northwest Indiana’s Big Mac Under Glass Gala

#12 Benefit
The gala took place at the massive Aragon Ballroom this year, had 200 auction packages, and raised more than $500,000. KC and the Sunshine Band performed. Next: Spring 2013
The gala took place at the massive Aragon Ballroom this year, had 200 auction packages, and raised more than $500,000. KC and the Sunshine Band performed. Next: Spring 2013
Photo: Courtesy of Bob Milkovich at Ronald McDonald House Charities of Chicagoland & Northwest Indiana’s Big Mac Under Glass Gala
12. Cystic Fibrosis Foundation’s Grand Chef’s Gala

#13 Benefit (up from #14)
In 2012, the food-focused event had a Havana theme, drew 1,200 guests including corporate leaders restaurant-industry bigwigs, and raised $500,000. Next: January 2013
In 2012, the food-focused event had a Havana theme, drew 1,200 guests including corporate leaders restaurant-industry bigwigs, and raised $500,000. Next: January 2013
Photo: Chris Guillen
13. N’Digo Foundation Gala

#14 Benefit (up from #15)
The attention-grabbing gala gets major corporate support from companies such as ComEd and Blue Cross Blue Shield. This year, more than 1,000 guests attended the N’Digo Foundation Gala and Aretha Franklin headlined. Next: Summer 2013
The attention-grabbing gala gets major corporate support from companies such as ComEd and Blue Cross Blue Shield. This year, more than 1,000 guests attended the N’Digo Foundation Gala and Aretha Franklin headlined. Next: Summer 2013
Photo: Courtesy of the N'Digo Foundatio
14. After School Matters Gala

#15 Benefit
The gala supports the charity founded by Chicago’s beloved former first lady Maggie Daley. The 2011 After School Matters Gala drew 1,500 guests. This year’s event—with new chairs since Daley’s recent passing—takes place on Navy Pier with performances and a fireworks show. Next: October 1, 2012
The gala supports the charity founded by Chicago’s beloved former first lady Maggie Daley. The 2011 After School Matters Gala drew 1,500 guests. This year’s event—with new chairs since Daley’s recent passing—takes place on Navy Pier with performances and a fireworks show. Next: October 1, 2012
Photo: Rick Aguilar
15. Children’s Research Fund’s Children’s Ball

#16 Benefit
The glitzy gala celebrated a year of $2 million fund-raising activity in 2011 with more than 1,000 guests. This year’s event at the Hilton Chicago has the theme “Lifesavers: Keeping Hope Afloat.” Next: December 8, 2012
The glitzy gala celebrated a year of $2 million fund-raising activity in 2011 with more than 1,000 guests. This year’s event at the Hilton Chicago has the theme “Lifesavers: Keeping Hope Afloat.” Next: December 8, 2012
Photo: Courtesy of Children's Research Fund's Children's Ball
16. American Heart Association’s Heart Ball

#17 Benefit
The heart-healthy event—the meal is always reflective of the cause—counts big players from the medical community among its 800 guests. The American Heart Association’s Heart Ball raised $1.6 million in 2012. Next: April 13, 2013
The heart-healthy event—the meal is always reflective of the cause—counts big players from the medical community among its 800 guests. The American Heart Association’s Heart Ball raised $1.6 million in 2012. Next: April 13, 2013
Photo: Carasco Photography/Deseo Events
17. Friends of Prentice Gala

#18 Benefit
Benefiting the Northwestern Memorial Hospital, the high-profile Friends of Prentice Gala typically draws an 800-guest crowd to Navy Pier and raises around $1 million. Next: Summer 2013
Benefiting the Northwestern Memorial Hospital, the high-profile Friends of Prentice Gala typically draws an 800-guest crowd to Navy Pier and raises around $1 million. Next: Summer 2013
Photo: Dan Rest
18. Brookfield Zoo Whirl

#19 Benefit
This year, the springtime gala offered its 800 guests a peek at a live cheetah, raked in $1.3 million, and was supported by the likes of American Airlines. Next: Spring 2013
This year, the springtime gala offered its 800 guests a peek at a live cheetah, raked in $1.3 million, and was supported by the likes of American Airlines. Next: Spring 2013
Photo: Robert Milkovich
19. The Boys & Girls Clubs Summer Ball

#20 Benefit (up from #24)
This year, the 600-guest event took place at the Radisson Blu Aqua Hotel with an "Aqua" theme and raised $1 million. Next: Summer 2013
This year, the 600-guest event took place at the Radisson Blu Aqua Hotel with an "Aqua" theme and raised $1 million. Next: Summer 2013
Photo: Bob Carl
20. Alzheimer’s Association’s Rita Hayworth Gala

#21 Benefit
The gala is chaired by Rita Hayworth’s daughter, Princess Yasmin Aga Kahn, and always has a theme inspired by one of the legendary actress’s movies. This year, the Alzheimer’s Association’s Rita Hayworth Gala raked in more than $1 million. Next: May 11, 2013
The gala is chaired by Rita Hayworth’s daughter, Princess Yasmin Aga Kahn, and always has a theme inspired by one of the legendary actress’s movies. This year, the Alzheimer’s Association’s Rita Hayworth Gala raked in more than $1 million. Next: May 11, 2013
Photo: Bill Richert
21. Adler Planetarium’s Celestial Ball

#22 Benefit (up from #26)
The planetarium’s largest annual event typically draws 600 guests and raises more than $1 million; each year, a corporation is honored. This year the Adler Planetarium’s Celestial Ball has a "Milky Way" theme. Next: September 8, 2012
The planetarium’s largest annual event typically draws 600 guests and raises more than $1 million; each year, a corporation is honored. This year the Adler Planetarium’s Celestial Ball has a "Milky Way" theme. Next: September 8, 2012
Photo: Ballogg Photography for Event Creative
22. Rehabilitation Institute of Chicago’s Medicine Ball

#23 Benefit
Held at the Peninsula, the event had an "old Havana" theme this year and netted $750,000. Next: May 2013
Held at the Peninsula, the event had an "old Havana" theme this year and netted $750,000. Next: May 2013
Photo: Dan Rest
23. Chicago Botanic Garden’s Summer Dinner Dance

#24 Benefit (new to the list)
The summer event draws the cream of North Shore society to Chicago Botanic Garden’s grounds for an elegant evening replete with a Veuve Clicquot champagne reception. Next: June 2013
The summer event draws the cream of North Shore society to Chicago Botanic Garden’s grounds for an elegant evening replete with a Veuve Clicquot champagne reception. Next: June 2013
Photo: Robin J. Carlson
1. The School of the Art Institute of Chicago Fashion Show

#1 Fashion & Retail Event
The highly produced show displays 300 student designs and has had high-profile honorees such as Cynthia Rowley and Ikram Goldman. Next: Spring 2013
The highly produced show displays 300 student designs and has had high-profile honorees such as Cynthia Rowley and Ikram Goldman. Next: Spring 2013
Photo: Sara Condo
2. Fashion Focus

#3 Fashion & Retail Event
The weeklong event highlights the work of local designers and comprises around 30 free and ticketed events including runway shows in Millennium Park. Next: October 15-21, 2012
The weeklong event highlights the work of local designers and comprises around 30 free and ticketed events including runway shows in Millennium Park. Next: October 15-21, 2012
Photo: Meg Bradley/Stephen Green Photography
3. Macy’s Glamorama

#4 Fashion & Retail Event
Glamorama includes a fashion show and headline performance followed by a massive after-party with over-the-top brand activations. This year’s event has a British theme and takes place at a new venue, the Harris Theater. Next: August 10, 2012
Glamorama includes a fashion show and headline performance followed by a massive after-party with over-the-top brand activations. This year’s event has a British theme and takes place at a new venue, the Harris Theater. Next: August 10, 2012
Photo: Adam M. Bettcher for Macy's
4. Akira’s Garden of Eden Fall Fashion Show

#5 Fashion & Retail Event (new to the list)
The show displays more than 100 looks from the local fashion house and has bars and pop-up shops on-site; last year the event moved to the Grossinger Auto Complex to accommodate a whopping 3,000 guests. Next: September 23, 2012
The show displays more than 100 looks from the local fashion house and has bars and pop-up shops on-site; last year the event moved to the Grossinger Auto Complex to accommodate a whopping 3,000 guests. Next: September 23, 2012
Photo: Sebastian Biedron Photography
5. St. Jude’s Dream a Little Dream Luncheon and Fashion Show

#6 Fashion & Retail Event
Last year, the show sold out with 1,540 guests and showcased a holiday collection from Project Runway’s Peach Carr. Next: November 11, 2012
Last year, the show sold out with 1,540 guests and showcased a holiday collection from Project Runway’s Peach Carr. Next: November 11, 2012
Photo: Courtesy of St. Jude Dream a Little Dream Fashion Show
6. Rush University Medical Center’s Fashion Show

#7 Fashion & Retail Event
Now in its 86th year, Rush University Medical Center’s Fashion Show is the longest continuously running charitable fashion show in North America. In 2009, it moved to the Palmer House Hilton and got a splashy new look. Next: October 18, 2012
Now in its 86th year, Rush University Medical Center’s Fashion Show is the longest continuously running charitable fashion show in North America. In 2009, it moved to the Palmer House Hilton and got a splashy new look. Next: October 18, 2012
Photo: Bob Carl
7. Lurie Children’s Hopsital’s Gold Coast Fashion Award Show

#8 Fashion & Retail Event
The event showcases fashion from local boutiques, major retailers, and designers; it also has a competition segment that lets guests act as judges. In the past, big name fashion folks such as Monique L'huiller have attended. Next: September 28, 2012
The event showcases fashion from local boutiques, major retailers, and designers; it also has a competition segment that lets guests act as judges. In the past, big name fashion folks such as Monique L'huiller have attended. Next: September 28, 2012
Photo: Robert F. Carl
8. Fashion Columbia

#9 Fashion & Retail Event (new to the list)
The annual showcase for Columbia College’s student designers had sponsorship from Mercedes-Benz this year and was chaired by Johnson Publishing C.E.O. Desiree Rogers. Big-name industry folks, including Ikram Goldman, attended. Next: June 2013
The annual showcase for Columbia College’s student designers had sponsorship from Mercedes-Benz this year and was chaired by Johnson Publishing C.E.O. Desiree Rogers. Big-name industry folks, including Ikram Goldman, attended. Next: June 2013
Photo: SB Media Inc.