Chicago

#1 Theater, Dance & Music Event (up from #2)
More than 3,300 opera fans gathered at the Lyric Opera for the opening-night performance of Verdi’s Otello. Afterwards, some 550 guests boarded buses and headed to a lavish dinner-dance at the Chicago Hilton. The event netted approximately $900,000. The 2014 event will celebrate the Lyric’s 60th anniversary and will have a special, new format to mark the occasion; a separate concert and gala for the anniversary will be held November 1. Next: September 27, 2014

#2 Theater, Dance & Music Event
This year’s event kicked off with a performance of Verdi’s classics at the Symphony Center for 2,000 guests; for the first time, there was an open bar. The ensuing ball for 700 patrons was held at the Palmer House Hilton, eliminating the need for trolleys. The gala raised around $1.2 million. Next: September 20, 2014

#3 Theater, Dance & Music Event (up from #6)
The nation’s biggest comedy festival features stand-up comedy, sketch shows, and films in major venues throughout the city, including the Chicago Theatre. The talent includes comedy’s biggest names: this year, Seth Meyers, Bill Maher, and Russell Brand headlined. A major change to the 2013 iteration was the new Digital Comedy Hub at Stage 773. Next: Summer 2014

#4 Theater, Dance & Music Event
The 2013 event included a performance at the Auditorium Theatre and cocktails, dinner, and a Blue Star Lounge-theme after-party at the Hilton Chicago. The gala had more live-auction prizes this year and ultimately raised $1.23 million. Next: April 25, 2014

#5 Theater, Dance & Music Event
This year’s famous-actor-studded gala raised $1.1 million. The 600 guests also included corporate, civic, and cultural leaders. The live auction had unique prizes donated by the company’s actors. Next: May 3, 2014

#6 Theater, Dance & Music Event (up from #7)
With 800 guests, this year’s event featured a performance from world-renowned pianist Lang Lang and marked the first time that a gala concert had a sold-out pavilion with record attendance on the lawn. The event raked in $1.2 million. Next: July 26, 2014

#7 Theater, Dance & Music Event (up from #12)
Stephen Colbert hosted the buzzed-about gala in 2013, which broke significant ground by raising $1 million from 500 guests. In 2012, the event raised only $600,000. Next: March 2013

#8 Theater, Dance & Music Event
Inspired by the then-upcoming performance of The Jungle Book, this year’s event had animal-filled decor and an exotic menu. It drew some 700 guests and raised more than $1 million. Next: Spring 2014

#9 Theater, Dance & Music Event
The 2013 event included the presentation of the Spirit of Shakespeare awards to civic honoree Richard M. Daley and artistic honoree Stephen Sondheim. Major stars of the international theater community, including Audra McDonald, were among the 550 guests in attendance, and the gala raised $1.1 million. Next: June 16, 2014

#10 Theater, Dance & Music Event
The 35th anniversary gala in May honored Mayor Rahm Emanuel and JPMorgan Chase. With 700 guests, the evening raised more than 1.1 million. Next year’s gala honors Mikhail Baryshnikov. Next: May 19, 2014

#11 Theater, Dance & Music Event
The Chicago Dancing Festival started as a one-day affair and now offers several days of free programming in various venues. This year’s event placed emphasis on local dance companies and featured performances of diverse styles ranging from ballet to classical Indian. Next: August 18-23, 2014

#12 Theater, Dance & Music Event (up from #13)
A nearly indescribable evening of puppetry, pageants, and more, the theater's gala is a hotly anticipated event each year. This year’s bash took place in the theater’s new Pilsen home base and raised more than $400,000. Next: March 15, 2014

#13 Theater, Dance & Music Event
With honorees including Scandal’s Jeff Perry, the gala took place this year at the InterContinental Chicago Magnificent Mile. Raising funds to support area companies, the event had sponsors such as The Chicago Tribune and Boeing. Next: Spring 2014 

#14 Theater, Dance & Music Event
Held at Architectural Artifacts, the event had a Circus Maximus theme. Raising funds for the company for L.G.B.T. youth, the ball had sponsors including BMO Harris and Blue Cross Blue Shield of Illinois. It drew around 450 guests and raised more than $85,000. Next: Spring 2014

#1 Festival
The fest drew a record-breaking 100,000 music fans per day to Grant Park this year with 130-some acts including Nine Inch Nails, the Cure, and Phoenix. And to attract top ticket holders, a new Platinum Pass granted unprecedented perks like an open bar and elevated viewing areas. Next: August 1-3, 2014

#2 Festival
Founded in 2006, the increasingly popular event draws an average of 18,000 fans a day and—with weekend passes going for $120 a pop—is appreciated as one of the more affordable major music fests. This year’s event offered performances from the likes of Björk and R. Kelly, with higher production levels than in years past. Meanwhile, brands such as Popchips, Vans, and Zipcar had a major footprint on festival grounds. Next: July 2014

#3 Festival (up from #6)
Presented by Bon Appétit, Chicago Gourmet is arguably the city’s most prestigious food and wine event, and it’s growing every year. The festival’s attendance increases consistently: 12,456 guests made it out this fall, as compared to around 10,000 last year, and 6,000 when the event began in 2008. There were more big-name chefs than ever this year—a total of 175 participated—and there was also more food. The 11 tasting pavilions included new ones like dessert and La Femme du Chef, and new highlights to the programming included “Chef Smackdowns” in fun categories such as meatballs and tacos. Plus, the festival’s popular opening-night fete, the Hamburger Hop, grew in 2013 with its own after-party and a record-breaking 1,100 guests in attendance. Next: September 26-28, 2014

#4 Festival (up from #7)
There was good news for Chicago’s signature food festival this year: the fest was profitable for the first time since 2007, generating $272,000. In an effort to revitalize the event, organizers brought in new attractions including food trucks. Concerts each night featured buzzy headliners like Robin Thicke, and the 35 restaurants represented on site included some newcomers. Attendance also increased with 1.5 million guests this year as opposed 1.2 million in 2012. Next: July 9-13, 2014

#5 Festival
Held over Labor Day weekend, the Chicago Jazz Festival is a 35-year-old tradition. For the first time this year, the event relocated from Grant Park—which, some guests complained, had subpar acoustics—and set up shop in Millennium Park. The 2013 fest also had Friday-afternoon concerts, which had not been offered since 1997, plus a full day of Thursday programming at the Chicago Cultural Center. Estimated attendance was 125,000. Next: August 29-31, 2014

#6 Festival
The local tradition was significantly scaled down this year due to federal budget cuts. Gone were the beloved Blue Angels and the Thunderbirds, though they were replaced with new acts. Among the first-time headliners were the Geico SkyTypers who wrote text-message-like phrases in the sky. Some 1.7 million spectators took in the event, down from the typical two million. The Blue Angels are likely to return next year. Next: August 2014

#7 Festival
Billed as the world’s largest free blues festival, the musical happening celebrated its 30th anniversary in June. With a “Rollin’ Up the River” theme, the Grant Park event drew 500,000 music fans and had sponsors including Pepsi and Humana. New touches included an opening-night concert at Millennium Park’s Jay Pritzker Pavilion, where artists such as Shemekia Copeland performed. Next: June 13-15, 2014

#9 Festival
Known as the largest weekend street fair in the Midwest, the event typically draws some 100,000 guests. Occupying six city blocks, the fest offered three stages with entertainment from bands like Wilson Phillips. There were also about 400 vendors offering food, arts, and crafts. Next: August 9-10, 2014

#10 Festival
The largest annual outdoor dancing series in the United States is held in Grant Park’s Spirit of Music Garden, offering free dance classes in styles ranging from tango to Irish folk. Chicago SummerDance sees some 1,200 participants gather at each session; at the conclusion of the classes, live bands take the stage and guests test out new moves on the alfresco dance floor. Next: Summer 2014

#11 Festival (up from #12)
Presented by The Chicago Tribune, the Lit Fest is the Midwest’s largest free, outdoor literary event. Featuring authors like Lauren Weisberger, this year’s event included readings, book signings, author conversations, poetry slams, and, of course, a book fair. There were also cooking demos with celebrity chefs-cum-cookbook-authors including Rick Bayless. Next: June 2014

#1 Art & Architecture Event
North America’s largest commercial-furnishings trade show and conference takes place at the Merchandise Mart. It draws more than 40,000 architecture and design pros and offers 100 seminars, forums, and keynote addresses. The trade show features wares from more than 700 showrooms and exhibitors. Next: June 9-11, 2014 

#2 Art & Architecture Event
An acronym for Sculptural Objects and Functional Art, the expo is Chicago’s longest continuously running art fair. The event, which typically attracts some 30,000 visitors, was purchased by Urban Expositions in June. The show management company plans to develop a new art-and-design-fair division, which will have SOFA as its flagship. Connect, a student-design exhibition and competition, was new to the fair this year. Next: October 31-November 2, 2014

#3 Art & Architecture Event (new to the list)
This year the International Exposition of Contemporary and Modern Art featured works from 125 leading art galleries from 17 countries. The event, held on Navy Pier, drew 30,000 visitors. The highly stylish exhibition is designed by star architect Jeanne Gang. Next: September 18-21, 2014

#4 Art & Architecture Event
Dubbed “Beauty and the Feast,” this year’s showcase of tabletop design included detailed vignettes from prominent architects, artists, and interior designers. The three-day event includes an opening cocktail party that draws 1,000 guests; there’s also a popular public viewing, a tasting event, and a glamorous closing-night gala. Proceeds from Dining by Design benefit the Design Industries Foundation Fighting AIDS. Next: November 2014

#5 Art & Architecture Event (new to the list)
Billed as one of the country’s top art fairs, the event draws 40,000 art lovers to Old Town each year. It showcases works from about 250 artists from across the country. The event also includes a garden walk, a children’s corner, and a music stage. Next: June 14-15, 2014

#6 Art & Architecture Event
Always bursting with innovative ideas, the gala has an edgy, artsy vibe that matches its moniker. This year’s event in February took place at the museum’s warehouse for the first time and had a factory theme. The event drew 500 guests—including Mayor Rahm Emanuel—and raised $900,000. Next: September 20, 2014

#7 Art & Architecture Event
The museum’s largest annual fund-raiser always corresponds with the opening of a major exhibition. Sponsored by Graff, this year’s June affair marked the arrival of "Impressionism, Fashion, and Modernity" and had an appropriately Parisian vibe. About 575 guests attended, and tickets sold for $1,000. Next year’s event will celebrate the Magritte exhibition. Next: June 20, 2014

#8 Art & Architecture Event
The 58th iteration of the prestigious award ceremony took place at Navy Pier in late October. With big-name sponsors such as Benjamin Moore and Gensler, the evening presented awards in categories such as “Divine Detail” and “Sustainability” in front of an audience of 800 industry pros. Next: Fall 2014 

#9 Art & Architecture Event
Held during NeoCon, this year's black-tie gala honored the winners of two highly prestigious industry awards: the 40th annual Interior Design Competition and the 21st annual Will Ching Design Competition. The splashy affair took place at the Ritz-Carlton Chicago and drew interior designers and design manufacturers from around the world. Next: June 8, 2014

#10 Art & Architecture Event
The Illinois Chapter of the U.S. Green Building Council hosts the popular industry function to honor eco-minded business leaders, government officials, and building practitioners. Held in May, the 2013 event took over the National Hellenic Museum and doled out Emerald Awards in categories such as “Green Innovation: Green School.” Next: Spring 2014

#1 Trade Show & Convention
North America’s largest and longest-running auto show spans 1.3 million square feet. Nearly 1,000 total vehicles are on display, and the show also has events including the massive First Look for Charity bash, held the night before its official opening. Next: February 8-17, 2014

#2 Trade Show & Convention
Each year, more than 1,800 exhibitors and thousands of buyers converge at McCormick Place for the event designed to drive profitability and forge industry connections. The show is co-located with the International Wine, Spirits & Beer event, which will expand into the Lakeside Ballroom next year. Next: May 17-20, 2014

#3 Trade Show & Convention
Billed as the world’s premier housewares marketplace, the convention features 2,100 exhibitors and draws more than 20,000 buyers. There are international pavilions and display areas divided into themes such as “Dine and Design” and “Clean, Contain, and Sustain.” Next: March 15-18, 2014 

#4 Trade Show & Convention
The scientific event is held at McCormick Place and showcases new technology from nearly 700 exhibitors. This year, Condoleezza Rice will deliver a special lecture; some 50,000 attendees are expected. Next: December 1-6, 2013

#5 Trade Show & Convention (up from #6)
The show began in 2010 with 27,500 attendees; now, it draws around 41,000 guests, including an average of 900 members of the press. The buzzy show garners two million media impressions each year. Next: April 25-27, 2014

#6 Trade Show & Convention
Owned and produced by the salon professionals of Cosmetologists Chicago, the show draws around 50,000 industry pros. It also offers appearances by industry stars like Tabatha Coffey. Next: March 22-24, 2014

#7 Trade Show & Convention
This year’s sold-out show had 600 exhibitors, demonstrating double-digit growth, and there were more than 15,000 qualified industry professionals in attendance. The new Shopper Solutions Theater had standing-room-only learning labs. Next: May 20-22, 2014 

#8 Trade Show & Convention
One of the graphic communications industry’s foremost trade shows, the event explores print, online, and mobile realms. The event is co-located with the Converting & Package Printing Expo, so it offers two buyer audiences at one show. Next: September 28-October 1, 2014

#9 Trade Show & Convention
Held over the Martin Luther King Jr. holiday weekend, the family-friendly show offers bargains on boats, R.V.s, marine accessories, and more—including a life-size pirate ship and other attractions for kids. The attendance in 2013 was about 35,400, which marked a seven percent increase from previous years despite inclement weather. Next: January 16-20, 2014 

#1 Benefit
The prestigious ball, which is used as a model fund-raiser for other society chapters, raised $2.1 million this year. Nearly 900 guests and volunteers gathered at the Radisson Blu Aqua Hotel for a night that included entertainment from comedian Billy Gardell and high-style design from Heffernan Morgan Ronsley. During the always-lively auction, a golden retriever puppy fetched an $84,000 bid. Next: April 26, 2014

#2 Benefit (new to the list)
Some 3,500 guests turned out to this year's Willy Wonka-theme event, marking a record attendance. A benefit for the Gateway Green, the ball is one of Chicago’s best-known benefits and is particularly popular among the young-philanthropist crowd. Next: September 2014 

#3 Benefit
The huge gathering at McCormick Place traditionally draws 2,000 guests and raises more than $3 million. Smokey Robinson is slated to perform at this year’s event. Next: December 14, 2013

#4 Benefit
The event raises around $2 million each year and draws 1,700 guests. Celebrity attendees have included Steve Harvey, Phylicia Rashad, and Gladys Knight. Next: November 9, 2014

#5 Benefit
The glitzy night at the museum raked in more than $2 million this year and had unusual auction prizes: one guest bid $10,000 to drink out of the Stanley Cup. The evening also featured a surprise performance by Buddy Guy and drew nearly 900 guests. Next: Fall 2014

#6 Benefit (up from #9)
Dubbed “A Fair to Remember: Chicago, 1893,” this year’s event let guests tour the temporary exhibition "Opening the Vaults: Wonders of the World’s Fair." The gala drew 700 guests and raised $2.1 million. Hanging Ferris wheels played into the decor. Next: October 25, 2014

#7 Benefit (up from #15)
Including a performance from local teens, this year’s event drew 900 guests and raised more than $2 million. Mayor Rahm Emanuel was in attendance, as were former Mayor Richard M. Daley, board chair Mellody Hobson, and Hobson’s husband, filmmaker George Lucas. Next: Fall 2014

#8 Benefit (up from #11)
With a superhero theme, the black-tie event included an appearance from comedian Martin Short and had higher production levels than in years past. It raised $1.3 million and saw 800 guests. The event also included video messages from actor Steve Carell, chef Rick Bayless, and more notable figures. In 2014, the event will move to a larger space at Soldier Field. Next: May 3, 2014

#9 Benefit
An author is seated at each table at the prominent fund-raiser, which draws international leaders in the literary industry. This year, honorees were Isabel Allende and Michael Lewis, and the event raised more than $1.5 million. The event drew a record-breaking 750 guests. Next: Fall 2014 

#10 Benefit
With a James Bond-inspired theme, this year’s gala showcased the new stingray exhibit and included an aquatic show, a dinner, and an after-party with a lavish dessert spread. It drew some 900 guests and raised more than $1.2 million. Next: June 7, 2014

#11 Benefit
More than 600 guests attended the museum's black-tie event, which raised more than $1.5 million. Guests took a tour of the butterfly sanctuary, and the evening’s then-new exhibit, “Savour Nature,” inspired vegetable-filled decor. Next: May 2, 2014

#12 Benefit
With a “Wild at Heart” theme, the summer gala raised more than $1 million for the Chicago institution. More than 900 guests attended, and there was a surprise performance from KC and the Sunshine Band. Next: July 11, 2014

#13 Benefit (up from #21)
This year, the event broke records in both attendance and funds raised: it drew 900 guests and raked in $1.5 million. A Mother’s-Day-weekend tradition, the gala is chaired by Rita Hayworth’s daughter, Princess Yasmin Aga Kahn. Next: May 10, 2014

#14 Benefit (up from #16)
The black-tie gala always gets a whimsical spin in honor of its young beneficiaries. New to this year’s event is a “science fair for grown-ups” during cocktail hour. Organizers expect 1,000 guests—up from 900 in 2012. Next: December 14, 2013

#15 Benefit (up from #17)
Held at Navy Pier’s Grand Ballroom, the event typically draws 850 guests representing Chicago’s business, medical, and social communities. This year, the association's big benefit raised more than $1.7 million. Next: April 12, 2014
 

#16 Benefit
With the theme “Oh, What a Night,” the gala this year drew nearly 1,100 guests and netted a record $1.4 million for the medical center and Advocate Children’s Hospital. The event’s ‘60s theme carried through to a dinner that included deviled eggs and wedge salad. Next: May 3, 2014

#17 Benefit
A costumed Ronald McDonald roamed the black-tie event for 900 guests. Held at the Sheraton Chicago Hotel & Towers, the gala had a masquerade theme and pulled in $900,000 for the organization. Next year’s event will have an Emerald City theme. Next: March 8, 2014

#18 Benefit
Chicago’s top-name chefs serve hors d’oeuvres at the glitzy evening for 750 guests. Presented by Fairmont Hotels and Resorts, the evening also includes a presentation of the Jean Banchet Awards for Culinary Excellence. In 2014, the event will have a St. Tropez theme. Next: January 31, 2014

#19 Benefit
With an “Into the Wild” theme, this year’s gala at Navy Pier drew more than 700 guests. The tropical theme translated into 15-foot trees decked with stuffed-animal monkeys and a tinsel waterfall that cascaded toward the dance floor. The event raised more than $1 million. Next: June 14, 2014

#20 Benefit (up from #22)
With more than 650 guests in attendance, this year’s event had an “Infinite Horizons” theme and decor in night-sky hues. It raised more than $1 million. Next: Fall 2014

#21 Benefit
During cocktail hour, the 625 guests interacted with a pink flamingo and a sloth; during dinner, a cheetah appeared on the dance floor. The animal-centric event grossed more than $1.24 million. Next: April 26, 2014

#22 Benefit
With a crowd of 500 guests, this year’s event was dubbed “the Crystal Ball” and had decor in hues of white and grey. It took place at the Radisson Blu Aqua Hotel and raised $1.1 million. Next: May 2014

#23 Benefit (up from #24)
The elegant summer event draws the cream of North Shore society to the grounds of the Chicago Botanic Garden. This year’s dance had a “Language of Flowers” theme with Victorian-inspired decor, and it raised $500,000. Some 350 guests attended. Next: June 13, 2014

#24 Benefit
Held at the Peninsula, the event this year drew more than 300 guests and raised more than $500,000. It offered entertainment from DJ Chris Cater, and the live-auction prizes included earrings from Harry Winston. Next: September 2014

#1 Fashion & Retail Event
Stars of the international fashion community converge in Chicago for the student fashion show and gala. Elle fashion news director Anne Slowey served as M.C at this year’s event, which honored designers Kate and Laura Mulleavy of Rodarte. Other notable guests have included designer Jason Wu and J. Crew creative director Jenna Lyons. Next: Spring 2014

#2 Fashion & Retail Event (up from #3)
Chicago’s fashion week includes runway shows in Millennium Park and other locales. There are also citywide affairs including trunk shows and in-store parties. This year, the event included new pop-up shops in the park. Next: Fall 2014

#3 Fashion & Retail Event
Open to trade only, StyleMax takes place at the Merchandise Mart and displays women’s apparel and accessories from more than 2,000 lines. The event is held each season. Next: February 1-3, 2014

#4 Fashion & Retail Event (up from #8)
Held at Hilton Chicago Hotel and Towers and a highlight on local socialite calendars, the prestigious fashion show highlights local retailers; it also has a unique competition segment that lets guests act as judges. Fashion industry bigwigs such as Monique L'huiller and Wes Gordon have attended, and retailers including Neiman Marcus have sponsored. Next: September 19, 2014

#5 Fashion & Retail Event
The charitable show displayed fall and winter trends to a crowd of 2,500 this year. Held at the massive Grossinger Auto Complex, the event offered restaurant tastings, spa services, and an after-party at Japonais. Reality TV star Kristin Cavallari hosted. Next: Fall 2014

#6 Fashion & Retail Event
With performances by Sheryl Crow and Cirque du Soleil, this year’s event included a fashion show featuring fall trends from designers like Calvin Klein. The after-party on the Harris Theater rooftop had sponsor activations from brands such as American Express. Next: August 2014

#7 Fashion & Retail Event
Held at the Donald E. Stephens Convention Center in Rosemont, the event draws more than 1,300 guests. It includes a raffle, a champagne reception, and a designer fashion show. Next: November, 2014

#8 Fashion & Retail Event
Now in its 87th year, the event is the longest continuously running charitable fashion show in North America. This year, it took place at the Palmer House Hilton and featured notable Chicagoans walking the runway in looks from 11 retailers, including Chalk and Ralph Lauren. With 700 guests, the event raised $500,000 for lung cancer research. Next: October 2014

#1 Sports Event
Due to the Boston Marathon bombings, event organizers implemented heightened security measures—including watchtowers near Buckingham Foundation—for this year’s Bank of America-sponsored race in October. The security was largely undetectable, though, and didn’t mar the experience for the two million spectators cheering on the runners. A record 39,115 runners finished this year—up from 37,475 in 2012. Next: October 12, 2014

#2 Sports Event
Horses, trainers, and jockeys from across the globe trot out at the Arlington Million, one of the most prestigious horse races in the world—and the richest. Reportedly, it was the first horse race to offer a million-dollar purse. Some 32,000 guests attend annually, and the race is broadcast on national TV. Next: August 2014

#3 Sports Event
The world’s largest eight-kilometer road race, the Bank of America-sponsored event had its largest number of registrants ever this year: 40,000. The event’s festive atmosphere doesn’t hurt its appeal, with many runners dressed in funny costumes, and a post-party where runners get drink tickets attached to their bib numbers. As 90 percent of participants are from Chicago and its suburbs, the event also has a strong feeling of community. Next: March 30, 2014

#4 Sports Event
About 30 miles of Lake Shore Drive are closed off to car traffic on the morning of the massive happening. To raise funds for the Active Transportation Alliance, some 20,000 cyclists pedal the clear stretch of Chicago’s iconic road. Next: May 2014

#5 Sports Event (up from #6)
This year 7,600 breast cancer survivors and supporters donned pink to walk or run in the world-famous 5K. The event took place on Mother’s Day for the first time this year, and the Daley family served as honorary chairs. The event inspired 10 TV segments, and corporate sponsor Wade Miquelon of Walgreen’s got the front page of The Sun-Times's Splash magazine the week of the race. Next: May 11, 2014

#6 Sports Event
One of the country’s largest triathlons, the event draws 7,000 athletes and is presented by Toyota. This year’s athletic affair introduced a new competition called the “Chicagoland Tri Series,” and there was also a new team challenge. Next: August 24, 2014

#7 Sports Event (up from #8)
This year’s event set a record: it raised $400,000 by the time the race stepped off. Additionally, its sponsorship dollars more than doubled from 2012. Performer CeCe Peniston appeared at the post-race festivities, and a record 324 volunteers assisted with the event. Next: October 2014

#8 Sports Event
Chicago’s largest nighttime biking event sets off at 1 a.m. and wends through a dozen neighborhoods, lures some 8,000 cyclists, and includes fun contests such as “Best Decorated Helmet.” Because of a changeover in event management, this year’s event was said to have some rough patches including disorganized registration. But organizers are working to iron out the kinks for next year. Next: Summer 2014

#9 Sports Event
Presented by Geico, the chilly outing benefits the Special Olympics. It invites athletes to leap into the freezing waters of Lake Michigan in the wintertime; this year, it drew around 6,300 plungers and raised more than $1.7 million. Next: February-March 2014

#10 Sports Event
One of Chicago’s largest pet-friendly affairs, Pets Are Worth Saving’s Run for Their Lives drew a record 5,000 runners—and 2,500 pups—this year. Sponsors included Purina Pro Plan and Commonwealth Edison. Next: Spring 2014

#11 Sports Event
With a 333-mile route, the event is billed as the world’s longest annual freshwater race. This year’s competition saw 301 boats and 2,472 crew members racing to Mackinac Island. Participation is by invite from the Chicago Yacht Club, and Veuve Clicquot is the presenting sponsor. Next: July 19, 2014

#1 Parade & Holiday Event
It's the oldest, largest African-American parade in the country and the second-largest annual parade in the nation, typically drawing 1.8 million spectators and 350 floats. The event is also broadcast on national TV and is viewed by 26 million people. The picnic draws around 150,000 guests. Next: August 9, 2014

#2 Parade & Holiday Event
The nation’s largest evening holiday celebration centers on a grand tree-lighting parade down Michigan Avenue, with Minnie and Mickey Mouse as the grand marshals. The festive affair lures one million locals and tourists and ends with a fireworks display over the Chicago River. Next: November 2014

#3 Parade & Holiday Event
The upbeat event drew a record crowd of one million this year, which marked quite a leap from the 850,000 attendees in 2012. Next: June 2014

#4 Parade & Holiday Event
Presented by the Chicago Festival Association, the holiday event celebrates its 80th anniversary this month. The event will include a dozen character balloons, national marching bands, floats, and celebrity guests; some 1,000 volunteers helped coordinate the massive, nationally broadcast affair. Next: November 28, 2013

#5 Parade & Holiday Event
Set on Daley Plaza, the German-style village has wooden huts, roasted nuts, and a massive Christmas tree. The event got an oversize Advents calendar in 2011 and a new “Kindern Korner” in 2012. This year’s event will have the first Christkind—a fairylike character who doles out gifts to children. Next: November 26-December 24, 2013
 

#6 Parade & Holiday Event
Using 45 pounds of vegetable dye, organizers famously dye the Chicago River green for the annual celebration of Irish culture. The procession takes place every year on the Saturday before St. Patrick's Day, and around 400,000 spectators make it out. Next: March 15, 2014

#7 Parade & Holiday Event
With mariachi bands, flamenco dancers, and dancing, the parade is one of Chicago’s most colorful events. It’s also one of the country’s largest celebrations of Hispanic culture, drawing 500,000 spectators. Next: September 2014

#8 Parade & Holiday Event
This year, the downtown parade joined forces with Humboldt Park’s neighborhood parade, known as “the Puerto Rican People’s Parade.” The combined, larger celebration in Humboldt Park had music, carnival rides, and plenty of plantains—it also brought about 15,000 new guests to the northwest-side neighborhood. Next: June 14, 2014

#9 Parade & Holiday Event
A tradition since 1870, the event is one of the nation’s largest Memorial Day parades. This year, former director of the Central Intelligence Agency and United States Defense Secretary Leon Panetta served as the grand marshal. Next: May 26, 2014

#10 Parade & Holiday Event
Produced by the Joint Civic Committee of Italian Americans, the event includes a special mass at the Shrine of Our Lady of Pompeii and a wreath-laying ceremony in Arrigo Park. The parade—which travels down Columbus Drive—sees about 150 floats, bands, and marching units. Next: October 13, 2014

#11 Parade & Holiday Event
One of Chicago’s biggest charitable traditions, the warm-hearted parade sees thousands of motorcyclists collecting donations for underprivileged children. Many of the cyclists wear Santa suits and deck their motorcycles with ornaments. Next: December 1, 2013

#12 Parade & Holiday Event
Held the night before New Year’s Eve, the massive bash at Union Station draws around 2,000 young professionals. Sponsors have included Ariel Investments and Edelman, and proceeds benefit Hindsight. Next: December 30, 2013

#13 Parade & Holiday Event
More than 1,200 guests gathered at the Hilton Chicago last year for the sugary fete, which offered lavish treats from 30 confectioners and pastry chefs. This year’s event takes place at Union Station for the first time. Next: December 6, 2013