#1 Theater, Dance & Music Event
This year, the esteemed ball celebrated the close of the symphony's 125th anniversary season. With 600 guests—an increase from 500 in 2015—the evening kicked off with a cocktail reception followed by a program that recreated the symphony's first-ever concert on October 16, 1891. Afterward, guests headed to a gala celebration at the nearby Palmer House Hilton, and partook in cocktails, dinner, and dancing in the hotel's famous Red Lacquer Room. The night raised $1.5 million. Next: Fall 2017
Photo: Todd Rosenberg
#2 Theater, Dance & Music Event
The glamorous evening kicked off with red-carpet entrances featuring opera stars and notable Chicago residents—including Mayor Rahm Emanuel. Some 3,500 guests watched the first installment of Wagner's Ring cycle, Das Rheingold. Afterwards, guests attending the opening-night gala headed to the Hilton Chicago, where HMR Designs decked the ballroom in blue hydrangeas and blue-green lighting inspired by the Rhine River. Next: Fall 2017
Photo: Jaclyn Simpson
#3 Theater, Dance & Music Event
More than 600 guests attended the benefit, which started with a cocktail reception at Steppenwolf’s new in-theater bar and coffee shop, Front Bar. The evening also included a performance followed by a live auction, dinner, and dancing in a tent that spanned the theater’s parking lot. The event raised $1.3 million. Next: Spring 2017
Photo: Donovan Foote
#4 Theater, Dance & Music Event (up from #5)
The gala celebrated its 50th anniversary with a performance from the Chicago Symphony Orchestra, conducted by James Levine. While 650 guests attended last year, this year’s gala drew some 700 attendees. It raised more than $1 million, which was on a par with the money raised last year. Event Creative’s decor included 9-foot, color-changing chandeliers. Next: July 2017
Photo:Patrick Gipson/Ravinia
#5 Theater, Dance & Music Event
This year’s gala honored the ballet company’s 60th anniversary. The evening began with a special performance at the Auditorium Theatre. Afterward, guests boarded trolleys and headed to a dinner-dance at the Hilton Chicago, where young dancers from the ballet’s Community Engagement program performed. Some 700 guests attended, including Mayor Rahm Emanuel. The gala raised more than $1 million. Next: Spring 2017
Photo: Dan Rest
#6 Theater, Dance & Music Event (up from #8)
Marking the 400th anniversary of Shakespeare’s death, this year’s gala raised a record $1.4 million. It drew 500 guests, as compared to 350 guests in 2015. Held at Navy Pier, the evening featured a performance from actor Alan Cumming. It culminated in a fireworks show set to live music from the Chicago Symphony Orchestra. Next: Spring 2017
Photo: Daniel Ribar
#7 Theater, Dance & Music Event
Held at the Fairmont Chicago, this year’s black-tie affair featured a performance from Broadway star and Scandal actor Norm Lewis, who sang show tunes. Some 500 guests attended the gala, which raised more than $850,000 for the theater. Next: May 2017
Photo: Courtesy of the Goodman Theatre
#8 Theater, Dance & Music Event
Billed as the nation’s largest dance festival, the event celebrated its 10th anniversary this year. The fest—held at indoor and outdoor venues throughout the city—featured 25 free performances. New programming included a world-themed showcase at Navy Pier called “Planet Chicago.” Next: Summer 2017
Photo: Cheryl Mann
#9 Theater, Dance & Music Event
The Chicago Children’s Choir feted its 60th anniversary at this year’s gala, which took place at the Geraghty. Some 750 guests attended this year, which marks a boost over the 600-guest attendance in 2015. The night featured a performance from choir alum and Broadway star Allison Semmes. Next: Fall 2017
Photo: Todd Rosenberg
#10 Theater, Dance & Music Event (up from #12)
The local theater company gave its gala a “Vaudeville” theme this year. Some 370 guests attended, raising $825,000, an increase from 2015’s take of $700,000. The benefit also took place at a new venue: Revel Fulton Market. Next: Spring 2017
Photo: Robert Carl
#11 Theater, Dance & Music Event (up from #13)
The ball always has an elaborate theme, and this year’s was “Dragstrip.” Some 400 guests attended the benefit for the L.G.B.T. theater company, and the event brought in $75,000, an increase from $60,000 in 2015. Event highlights included a custom beauty and wig shop, a punch-out prize wall, and performances from local drag performers. Next: Spring 2017
Photo: Timmy Samuel
#12 Theater, Dance & Music Event
Some 450 guests attended the ball, which raised more than $800,000. More than $225,000 of the total was raised the night of the event, with help from a live auction and paddle raise. The evening also included a performance at the Harris Theater, followed by a dinner-dance at the Radisson Blu Aqua Hotel. Next: Spring 2017
Photo: Robert Carl
#13 Theater, Dance & Music Event
This year’s event drew some 230 guests to the Chicago History Museum. The evening included an awards presentation, and raised $110,000 to support the programming at 240 member theater companies. Next: Spring 2017
Photo: Courtesy of the League of Chicago Theatres
#1 Art & Architecture Event
Registration rose 6 percent this year at the event, which is billed as North America’s largest commercial interiors show. Some 53,000 international guests attended the three-day function, which was the first to take place in the newly remodeled Merchandise Mart. Next: June 12-14, 2017
Photo: Courtesy of NeoCon
#2 Art & Architecture Event
The event—which was featured in national magazines including W—had a record attendance of more than 38,000 visitors, an increase from 35,000 in 2015. Held annually on Navy Pier, Expo Chicago also featured more galleries this year: 145 were represented in 2016, while 140 participated last year. Next: September 13-17, 2017
Photo: Cory Dewald
#3 Art & Architecture Event
An acronym for “Sculptural Objects and Functional Art,” the event showcases paintings, textiles, jewelry, and more from some 70 galleries. It takes place annually at Navy Pier; in 2015, the fair had an updated floor plan. It drew some 36,000 guests—including curators, art collectors, and museum reps—and had a number of special exhibits. Next: November 4-6, 2016
Photo: Courtesy of SOFA
#4 Art & Architecture Event
Hosted by Design Industries Foundation Fighting AIDS, the showcase of tabletop trends is held at the Merchandise Mart. The event features work from big-name interior designers, artists, and architects. This year, the event will feature a cocktail reception and chefs tasting, followed by a day for community viewing and a gala dinner. Next: November 2-3, 2016
Photo: Barry Brecheisen/BizBash
#5 Art & Architecture Event
The 67th annual event drew some 30,000 art-lovers this year. Around 250 artists—selected by an independent art jury—showcased works that included paintings and photography. The event also includes a Garden Walk through more than 50 homes. Next: June 2017
Photo: Courtesy of Old Town Triangle Association
#6 Art & Architecture Event
In 2017, the event, known as the oldest art fair with a jury in the Midwest, will celebrate its 70th anniversary. This year, the Hyde Park fair drew some 15,000 guests—despite drizzly weather—and showcased 30 area nonprofits in addition to artwork. Next: June 3-4, 2017
Photo: Courtesy of 57th Street Art Fair
#7 Art & Architecture Event (new to the list)
Billed as the Midwest’s largest interior design event, Design Chicago is now in its sixth year. Last year, the attraction—which features panel discussions, cocktail mixers, demonstrations, and more—drew some 2,000 guests. This year, attendance grew considerably: Some 3,000 industry-pros made it out to the event. Organizers credit the event’s growing recognition and high-profile speakers for the high turnout. Next: Fall 2017
Photo: Courtesy of Design Chicago
#8 Art & Architecture Event
The 62nd annual event returned to Navy Pier’s Grand Ballroom this year, offering a night of cocktails, dinner, and awards. Doled out in categories such as “Interior Architecture” and “Regional and Urban Design,” the awards recognize outstanding achievement in work from Chicago architecture firms. The evening typically draws some 1,000 guests. Next: Fall 2017
Photo: Courtesy of AIA Chicago
#9 Art & Architecture Event
The glitzy event drew some 500 design-industry professionals to the Ritz-Carlton, Chicago, this year. The evening’s centerpiece is an awards program, which recognizes the winners of the annual Interior Design Competition and the Will Ching Design Competition. According to organizers, the two competitions are regarded as the most prestigious in the interior-design profession. Next: June 11, 2017
Photo: John Wheeler
#10 Art & Architecture Event
The industry function celebrates eco-friendly building practitioners, business leaders, and government officials. This year, the gathering took place at the Chicago Cultural Center and drew some 400 guests. The evening also served as an introduction to the council’s new “Epic Challenge,” which will implement carbon draw-down strategies to improve sustainability in Chicago neighborhoods. Next: Summer 2017
Photo: Mark Campbell
#1 Festival
This year, the megawatt music fest celebrated its 25th anniversary and added another day to its lineup. The sold-out event—which spanned four days this year—featured performances from 170 acts, as opposed to 130 acts in 2015. Some 100,000 music fans flocked to the fest each day to hear music from the likes of the Red Hot Chili Peppers and Lana Del Rey. Next: August 3-6, 2017
Photo: Barry Brecheisen for BizBash
#2 Festival
Now in its 11th year, Pitchfork’s celebration of independent music takes place annually in Union Park, and draws around 50,000 guests. The 2016 lineup featured 40-some acts, among them Beach House and Sufjan Stevens. As usual, the fest included craft, record, and poster fairs, along with sponsor activations from brands like Vans. Next: July 2017
Photo: Barry Brecheisen for BizBash
#3 Festival
In 2016, the sold-out festival introduced the concept of a “host chef,” tapping the famed Rick Bayless to fill the role. For the first time, the event also had a theme: “Food is Art.” The fest featured some 250 chefs in tastings, demonstrations, and more; there were also separately ticketed events including the popular burger tasting, dubbed the “Hamburger Hop.” Total attendance was 13,694 guests. Next: September 22-24, 2017
Photo: Gail Reich
#4 Festival
Now in its 36th year, the outdoor food festival showcases bites from 67 local restaurants. This year, some 1.4 million guests tried snacks from smoked alligator sausage to upside-down caramel cupcakes. Other features included cooking demos, celebrity chef dinners, and concerts from the likes of Billy Idol. New features included a CH Distillery cocktail lounge where guests could sip Moscow Mules and other drinks. Next: Summer 2017
Photo: Walter S. Mitchell III/City of Chicago
#5 Festival
Known as the largest free event of its kind in the United States, the show features daredevil stunts from both military and civilian teams. Some two million fans flock to the lakefront to take in the show, which Shell has sponsored for 20 years. This year, rainy weather caused some delays, but the show carried on as usual and featured appearances from the U.S. Air Force Thunderbirds, the U.S. Army Parachute Team Golden Knights, and more. Next: August 2017
Photo: Courtesy of Chicago Air and Water Show
#6 Festival (up from #9)
Held in Chicago’s Douglas Park, the event that started as a punk and metal festival now features performances from some 130 bands. This year, the lineup featured the Flaming Lips, the Misfits, and Julian Marley. The event draws 160,000 attendees, and also offers a mini golf course, arcade games, and circus acts on site. This year, it was featured in The New York Times. Next: September 2017
Photo: Courtesy of Riot Fest
#7 Festival
The world’s largest free blues festival draws some 500,000 fans each year. Held in Grant Park during a scorching June weekend, this year’s 33rd annual affair saw headliners on four stages. The event also featured a panel discussion on “The Great Migration”—the mass movement of African Americans from the south in 1916—and a tribute to Otis Rush. Next: Spring 2017
Photo: Courtesy of Chicago Blues Festival
#8 Festival
The jazzy fest has been a local tradition since 1980. Held each year over Labor Day Weekend, the festivities include free performances from local and international artists. This year, guests took in performances from the likes of Orbert Davis and Benny Golson Quartet. Since 2016 also marked the centennial of the Great Migration, the event commemorated the anniversary with a newly commissioned work. Next: September 2017
Photo: Patrick L. Pyszka/City of Chicago
#9 Festival
Billed as a “think festival,” the weeklong gathering features 150 events, including talks and hands-on labs. This year, speakers included Skinnygirl Cocktail founder Bethenny Frankel, film and television producer Brian Grazer, and Hollywood agent Ari Emanuel. The fest drew some 30,000 attendees. Next: October 9-15, 2017
Photo: Courtesy of Ideas Week
#10 Festival
A tradition since the 1930s, the free music festival runs for 10 weeks each summer in Millennium Park. This year, highlights included a Cole Porter celebration and a movie night featuring Charlie Chaplin’s City of Lights, scored by the Grant Park Orchestra. Next: Summer 2017
Photo: Patrick L. Pyszka/City of Chicago
#11 Festival
Known as the largest outdoor street festival in the Midwest, the event celebrated its 35th anniversary in 2016. Some 180,000 guests gathered for the fair. The event featured arts, crafts, food, and drink vendors, as well as performances from Erika Jayne and the Chicago Gay Men’s Chorus. Next: August 12, 2017
Photo: Patrick L. Pyszka/City of Chicago
#12 Festival
Spanning five city blocks, the outdoor literary event draws around 150,000 guests. The event typically features 200 booksellers and 200 authors. This year’s fest featured appearances from the likes of former O.J. Simpson prosecutor Marcia Clark and cookbook author Dorie Greenspan. Next: June 2017
Photo: Courtesy of Printers Row
#13 Festival
Billed as the largest outdoor live music and dancing series in the United States, the event offers free dance classes in Grant Park’s Spirit of Music Garden. This year, the fest celebrated its 20th anniversary and featured 43 different bands; lessons covered swing dancing, waltzing, and more. Next: Summer 2017
Photo: Patrick L. Pyszka/City of Chicago
#1 Benefit (up from #2)
Benefiting programs for local teens, this year’s gala drew some 1,000 guests and raised an impressive $4.5 million. The coveted guest list always includes leaders of the corporate, philanthropic, and political communities. Held on Navy Pier, the buzzed-about night featured an art gallery filled with work from local teens; the After School Matters teens also performed a medley of Prince songs this year. Next: September 18, 2017
Photo: Juan Martinez
#2 Benefit
This year’s ball took place at a new venue: the Hilton Chicago. The event drew 800 guests (as opposed to 750 last year) and had a “soar beyond” theme. To match the theme, HMR Designs provided decor filled with clouds and butterflies. The event—which is highly regarded for its prestigious guest list and innovations, including being one of the first local galas to use electronic bidding—netted $2.4 million. Next: April 22, 2017
Photo: Ingrid Bonne
#3 Benefit
In 2015, the benefit featured a performance from REO Speedwagon and raised $4.2 million. It drew some 2,000 attendees and featured a silent auction with more than 400 packages. This year’s event will offer a performance from Cheap Trick. Next: December 10, 2016
Photo: Courtesy of JDRF
#4 Benefit
The event celebrated its 30th anniversary at Navy Pier this year. Some 1,000 guests attended the black-tie event, an increase from 960 guests in 2015. The event also raised more money this year, bringing in $2.3 million as opposed to $2 million last year. Actor and comedian Paul Reiser was the celebrity guest. Next: May 2017
Photo: Franz Perfect
#5 Benefit (up from #6)
This year, the event raised more than $2.2 million, a notable increase from the $1.52 million in 2015. Some 700 guests attended the ball, and they had the chance to interact with snakes—and check out the museum's live butterflies—during the cocktail hour. Other highlights included a meal featuring local ingredients prepared by Calihan Catering. Next: May 5, 2017
Correction: The date for next year's event has been updated.
Photo: Marcin Cymmer
#6 Benefit
This year’s black-tie gala had a “Dark Waters” theme. It raised $1.9 million and drew 700 guests. Highlights included the chance to view the aquarium's octopus; there was also a surprise performance from the Chicago Children’s Choir. And as guests left, they picked up snacks from a pop-up “taco cantina.” Next: June 2017
Photo: Dan Rest
#7 Benefit
Hosted by the Women’s Board of the Field Museum, the 2015 gala had a “Wonders of China” theme. The event drew some 550 guests and raised $2 million, which marked an increase over the $1.7 million raised in 2014. This year’s event will celebrate the board's 50th anniversary. Next: October 29, 2016
Photo: Cheri Eisenberg
#8 Benefit (up from #9)
Some 700 guests attended this year’s function, which again raised about $2 million for the Chicago museum. During the night, guests checked out two temporary exhibits: "Brick by Brick" and "Above and Beyond." Decor was inspired by a 1930s speakeasy, and entertainment included the glow-in-the-dark dance troupe iLuminate. Next: Fall 2017
Photo: Jeff Schear
#9 Benefit (up from #11)
The 34th annual Heart Ball raked in more than $2 million. Held once again at Navy Pier’s Grand Ballroom, the ball drew some 900 guests. Highlights included a heart-healthy dinner and a live auction. The event concluded with an after-party on the terrace. Next: April 2017
Photo: Bill Richert
#10 Benefit
The dinner will celebrate the Chicago Urban League’s 100th anniversary this year, and will mark the occasion with a performance from the iconic Diana Ross. Held annually at the Hilton Chicago, the evening typically draws around 1,700 guests and in 2015 raised more than $1.7 million. Next: November 19, 2016
Photo: Greg Davis/Powell Photography
#11 Benefit
More than 800 guests flocked to the Hilton Chicago for the 29th annual event, where Still Alice author Lisa Genova accepted the Rita Hayworth award. The event also included a violin show during the cocktail reception, a three-course dinner, a live auction, and live music. It raised more than $1 million. Next: May 13, 2017
Photo: Bill Richert
#12 Benefit
Iconic composer and lyricist Stephen Soundheim received the Carl Sandburg Literary Award the 2015 event; this year, honorees will include Erik Larson, Scott Turow, and Amina Gautier. The event attracts nearly 800 guests each year and typically raises around $1.5 million. Next: October 26, 2016
Photo: Johnny Knight
#13 Benefit
The Israel-based Weizmann Institute of Science hosts the annual benefit, which rakes in funds for its research programs. Last year, the event drew some 800 guests—including prominent business leaders and Mayor Rahm Emanuel—and raised a record-breaking $1.8 million. This year, the evening will honor civic leader and philanthropist Renee Crown. Next: October 29, 2016
Photo: Mitchell Canoff
#14 Benefit
This year’s elegant function had a “Penguins in Paradise” theme. Jewell Events Catering served penguin-shaped crackers and butter, and desserts came with glowing penguin statues that guests could take home. Some 850 guests attended in 2015, while this year’s crowd saw 900 guests. The festive affair raised some $1.35 million this year, up from $1.1 million in 2015. Next: July 2017
Photo: Alain Milotti
#15 Benefit
At the event, highlights include student scientists performing experiments at each dinner table. This year’s event had an Across the Universe theme, and drew some 600 guests. The evening raised $1.6 million for the Chicago institution. Next: September 2017
Photo: Courtesy of the Adler Planetarium
#16 Benefit (up from #18)
Animal encounters are a highlight at the black-tie event. This year, guests were able to get up close to a sloth, a porcupine, a penguin, and a llama named Cinnamon. Event Creative handled decor for the first time this year, giving the gala a look inspired by the African sunset. Some 600 guests attended, and the evening raised $1.29 million. Next: Spring 2017
Photo: Kelly Tone/Chicago Zoological Society
#17 Benefit
The 2015 benefit started off with a “science fair for grown-ups” and also included a dramatic staged reading featuring a physician, a patient, and a parent of a patient. The evening celebrated the $2.7 million brought in by the fund throughout the year; it drew 1,100 guests. Next: December 3, 2016
Photo: Ana Miyares
#18 Benefit
The 2016 gala took place for the first time at Navy Pier. Some 1,000 guests gathered at the event, which raised more than $400,000. The evening featured snacks from more than 35 local chefs, and was hosted by Food Network personality Jeff Mauro. Next: February 3, 2017
Photo: Caitlin Lisa
#19 Benefit (up from #21)
This year’s ball took place at the Hilton Chicago, and had a “Dream Big” theme. This year’s event drew some 450 guests, up from the 400 last year, and featured a live auction and live entertainment. The event raised more than $1.7 million, which marks an increase over 2015’s $1.4 million take. Next: Spring 2017
Photo: Robert Carl
#20 Benefit (up from #21)
The elegant evening took place at Morgan Manufacturing for the first time this year. The event drew some 500 guests—as opposed to 400 in 2015—and once again raised $1.5 million. Next: Fall 2017
Photo: Robert Carl
#21 Benefit (new to the list)
Now in its ninth year, the event drew 600 guests and raised some $1.2 million. For the first time, the gala moved from a hotel ballroom to take place in a raw event space: the Geraghty. The venue gave designers from Kehoe a blank canvas on which to create a striking, whimsical setting that included oversize paper daisies and a ceiling of suspended Slinkys. Singer Vanessa Williams performed. Next: Spring 2017
Photo: Ryan Sjostrom
#22 Benefit
Held annually at the Four Seasons Hotel, the evening is the sole fund-raising event for the volunteer board of Northwestern Memorial Hospital. This year’s event had a “Passport to Prentice” theme and drew 400 guests, raising nearly $1 million. Next: Fall 2017
Photo: Courtesy of Friends of Prentice
#23 Benefit
With a “Mission: Possible” theme, this year’s gala drew some 650 guests to the University of Illinois Chicago Forum. The gala raised about $500,000. And as usual, it featured an appearance from Ronald McDonald himself. Next: April 22, 2017
Photo: Elizabeth Harper
#24 Benefit
This annual event, which benefits the Chicago Gateway Green, celebrated its 25th anniversary this year. The event took place at Architectural Artifacts for the first time and featured a performance from renowned DJ Samantha Ronson. The event drew 1,000 guests and raised $400,000, a sizable increase from $257,000 in 2015. Next: Fall 2017
Photo: Mila Samokhina
#25 Benefit
Some 300 guests attended this year’s benefit, which raised $350,000. The evening offered cocktails in the rose garden, followed by dinner in a tent decorated by Kehoe Designs. After dinner, guests danced to the Stu Hirsh Orchestra. Next: June 2017
Photo: Robert F. Kusel
#1 Trade Show & Convention
The nation’s largest auto show hosted its 108th edition in 2016. This year’s event featured the global debut of more than 20 vehicles, as well as three indoor test tracks and a large array of concept cars. Though they don't release official numbers, organizers reported a 10 percent increase in attendance this year. Next: February 10-20, 2017
Photo: Courtesy of Chicago Auto Show
#2 Trade Show & Convention
The show is known as the world’s largest annual gathering for restaurant, lodging, and food-service pros—and this year, the event grew even larger. It drew more than 67,000 registrants (as opposed to 63,000 last year), and its footprint grew by 7 percent. The event is co-located with the Beverage Alcohol for Restaurants (or B.A.R.) show, which expanded with additional programming this year. The event draws restaurant-industry icons including celebrity chefs; it also inspires off-site events across the city. Next: May 20-23, 2017
Photo: Courtesy of the National Restaurant Association
#3 Trade Show & Convention
The 2016 show featured an updated look driven by new branding and graphics. Famous faces from chef Emeril Lagasse to country singer-turned-food-personality Trisha Yearwood appeared at the expo, which sold out more than 10 weeks in advance. This year’s show displayed housewares from some 2,100 exhibitors. The new “Discover Design” expo had 200 exhibitors. Next: March 18-21, 2017
Photo: Courtesy of International Housewares Association
#4 Trade Show & Convention
Focused on comics, anime, and other types of pop culture, the event began in 2010. This year, it drew 72,500 fans throughout the weekend and had a trade-show floor packed with 470 exhibitors. Organizers reported some 712 million media impressions. Next: April 21-23, 2017
Photo: Courtesy of Chicago Comic & Entertainment Expo
#5 Trade Show & Convention
The 94th annual show drew more than 70,000 salon professionals. More than 400 companies displayed new products in hair care, nail care, and skin care. There were also continuous trend presentations on three runways. Next: March 25-27, 2017
Photo: Courtesy of America's Beauty Show
#6 Trade Show & Convention
Nearly 17,000 industry pros attended this year’s expo, which offers four acres of cookies, candies, savory snacks, and chocolates. There were more than 750 exhibitors this year, and there was a 22 percent increase in exhibit space. Attendees prowl the show to learn about trends, which this year included unusual flavor pairings like mangoes and chocolate. Next: May 23-25, 2017
Photo: Courtesy of the National Confectioners Assocation
#7 Trade Show & Convention
The 101st annual gathering returned to McCormick Place in 2016. The theme was “Innovation Is the Key to Our Future,” and the event showcased the newest advances in radiology. The trade-show floor featured 659 exhibits, and organizers reported 51,922 registrants, including 1,372 guests who attended virtually. Next: November 27-December 2, 2016
Photo: Courtesy of the Radiological Society of North America
#8 Trade Show & Convention
Founded in Chicago in 2011, the event has since grown to include conferences in eight North American cities including Miami and Toronto. This year, new C.E.O. Amanda Signorelli oversaw the Chicago festival and focused on adding more talks and panels. Programming covered topics such as technical skills, hiring, and drones. Next: Summer 2017
Photo: Courtesy of Techweek
#9 Trade Show & Convention
Attendance was up at this year’s show, which was held at McCormick Place in January. It showcased boats and R.V.s, and had activities ranging from free sailing lessons to an R.V. buyers' seminar. Some 47,359 guests attended, a slight increase from 2015. Next: January 11-15, 2017
Photo: Courtesy of Marina Blevins
#1 Sports Event
Some 40,000 runners participated in this year’s massive race. Traveling through 29 Chicago neighborhoods, the event drew around 1.7 million spectators and was covered in national publications including Newsweek. Bank of America is the presenting sponsor. Next: October 8, 2017
Photo: Courtesy of Chicago Marathon
#2 Sports Event
Jockeys, horses, and trainers from all over the world gather at the event, which is known as the first event of its kind to offer a million-dollar purse. This year, a crowd of about 32,000 spectators watched as Mondaliste was named the winner. Next: Summer 2017
Photo: Courtesy of Arlington Million
#3 Sports Event
Sponsored by Bank of America, the eight-kilometer road race passes through downtown Chicago, and starts and finishes in Grant Park. The shuffle is regarded as the unofficial kickoff to the city’s outdoor running season, and many participants don festive green running gear. This year, about 23,000 runners participated. Next: April 2017
Photo: Courtesy of Bank of America
#4 Sports Event
Held over Memorial Day Weekend, the early-morning bike ride takes place along a 30-mile stretch of Lakeshore Drive. Local cyclists bike down a car-free road to raise money for the Active Transportation Alliance. The event typically draws some 20,000 cyclists. Next: May 2017
Photo: Anne Evans
#5 Sports Event
Special Olympics of Chicago broke its fund-raising goals in 2016 by raising some $1.5 million. The event also drew record participation, with some 6,000 guests plunging into the icy waters of Lake Michigan. Only 4,500 “plungers” attended in 2015. This year’s event saw several celebrity attendees—including Lady Gaga and Al Roker of NBC's Today show—and it also saw higher levels of corporate sponsorship. Next: March 5, 2017
Photo: Chicago PhotoPress
#6 Sports Event
Held annually on Mother’s Day, the event is part of the world’s largest series of 5K runs and fitness walks. This year, the race saw more than 8,000 runners, walkers, volunteers, and sponsors. Next: May 14, 2017
#7 Sports Event
Held on the shores of Lake Michigan, the competition is one of the largest triathlons in the world. In 2016, the event had more than 2,500 new participants, contributing to a total of more than 9,000 competitors. Some 30,000 spectators cheered the athletes on, and Transamerica was once again the title sponsor. Next: August 27, 2017
Photo: Ali Engin
#8 Sports Event
Despite windy, rainy weather, this year’s attendance stayed steady with some 2,500 runners. The event raked in more than $471,000 this year, which marks an increase over the $386,000 raised last year. The event’s opening ceremonies included a live performance from the Chicago Gay Man’s Chorus. Next: Fall 2017
Photo: John Gress
#9 Sports Event
Chicago’s largest nighttime biking event draws some 8,000 cyclists each year. The 25-mile ride kicks off at 10:30 p.m. with a pre-ride festival that includes live music, vendors, and contests for achievements such as “best decorated helmet.” This year, new attractions included a 4:30 a.m. “sunrise stretch,” hosted by Gratitude Yoga. Next: Summer 2017
Photo: Courtesy of L.A.T.E. Ride
#10 Sports Event (up from #11)
Billed as one of the oldest freshwater races in the world, the event celebrated its 108th anniversary in 2016. The 333-mile race kicks off at the Chicago Lighthouse, just east of Navy Pier, and ends at Mackinac Island. Participation is by invitation from the Chicago Yacht Club, and 326 boats participated this year. Parties include Michigan Avenue’s Ashore Thing presented by BMO Bank, which lets fans view the race from Navy Pier while sipping champagne. Next: July 2017
Photo: Jeff Schear
#11 Sports Event
The event combines a 5K, pet-friendly walk with a 5K run (the latter is “for humans only.”) Kicking off at Montrose Harbor, the event benefits homeless animals and lured around 3,000 participants—and 1,000 pups—this year. Attractions also includes splash pools for dogs, a “doggy buffet,” food trucks, and face painting. Next: Summer 2017
Photo: Rich Chen
#1 Fashion & Retail Event (up from #2)
The Midwest’s largest apparel and accessories trade show takes place each season at the Merchandise Mart. This year, the show had new features including an easier-to-navigate layout, new categories and brands, and added amenities such as daily lunches, cocktail parties, and informal modeling. The show is industry-only and is covered in major industry publications such as WWD. Next: January 22-24, 2017
Photo: Courtesy of StyleMax
#2 Fashion & Retail Event (up from #3)
The 61st annual Gold Coast Fashion Awards returned to Revel Fulton Market this year, raising some $1.1 million and drawing 900 guests. The evening included a cocktail reception with chef’s tasting stations, an after-party, and a fashion show that let the audience vote for their favorite emerging fashion designer. This year, eveningwear designer Michael De Paulo was the winner. Next: September 2017
Photo: Robert Carl
#3 Fashion & Retail Event (up from #6)
The country’s longest-running charitable fashion show celebrated its 90th anniversary in 2016. The show took place at the United Club at Soldier Field and featured a fashion show and a cocktail reception. Its guest list also grew, from 650 guests in 2015 to more than 780 guests this year. The night raised more than $500,000. Designer Adam Lippes was in attendance. Next: Fall 2017
Photo: Courtesy of Rush University
#4 Fashion & Retail Event
This year, the fashion show moved from Millennium Park to the Garfield Park Conservatory. It featured a runway show with student designs that drew some 300 guests; there was also a fashion exhibit that was open to the public throughout the weekend. Next: Spring 2017
Photo: James Prinz
#5 Fashion & Retail Event
In 2015, the 12-year-old St. Jude patient Mary Browder was the guest of honor at the emotionally stirring event. Held at the Donald E. Stephens Convention Center, the event drew some 1,300 guests and raised $455,000. This year, the event celebrates its 22nd year, and will include a raffle, a champagne reception, a luncheon, and a fashion show. Next: November 20, 2016
Photo: Courtesy of St. Jude's
#6 Fashion & Retail Event (up from #7)
Benefiting the Driehaus Design Initiative, the event features designs from local students. The runway show is judged by industry pros; the winner receives prizes such as cash and a garment display at Saks Fifth Avenue. This year’s event drew 400 guests and raised $170,000. Next: April 2017
Photo: Photo Affair Studio
#1 Parade & Holiday Event
The largest evening holiday celebration in the country, the festival centers on a grand parade down Michigan Avenue. In 2015, the event featured the lighting of some 200 trees along Michigan Avenue, and offered performances from Michelle Branch and other acts. Around 800,000 guests gathered to watch the festive proceedings. This year, the event will celebrate its 25th anniversary and will include more family-friendly activities. Next: November 19, 2016
Photo: Courtesy of Magnificent Mile Lights Festival
#2 Parade & Holiday Event (up from #3)
The iconic parade famously dyes the whole Chicago River green. The event also includes an Irish-theme parade with marching bands, floats, dancers, horses, and bagpipers. Around 400,000 spectators look on annually. Next: March 11, 2017
Photo: John W. Iwanski, CC BY-NC 2.0
#3 Parade & Holiday Event (up from #4)
The festive event, now in its 83rd year, is billed as the second-largest Thanksgiving parade in the country. It features 100 units, including its massive helium mascot Teddy the Turkey. This year, the complete parade will be broadcast live on WGN. Next: November 24, 2016
Photo: Courtesy of Chicago Festival Association
#4 Parade & Holiday Event
The country’s oldest and largest African-American parade was founded in 1929. Normally, the South-Side parade features some 300 participating units; this year, the event was shortened to reduce operating costs, and there were closer to 175 units. The event drew around one million spectators. Next: August 2017
#5 Parade & Holiday Event
Inspired by a German market, the Christmas festival features 60 wooden huts selling everything from hand-blown ornaments to beer steins and cuckoo clocks. Guests sip hot, spiced wine from boot-shaped mugs and snack on potato pancakes and strudel. Kids visit with a fairy-like character called the Christkind. Next: November 18-December 24, 2016
Photo: Tim Cartland
#6 Parade & Holiday Event
The L.G.B.T.-celebrating parade starts in Uptown and ends in Lincoln Park. Some 750,000 spectators gather to cheer on the colorful procession, which this year had a “Solidarity Through Pride” theme. In the wake of the shooting at the Orlando gay nightclub Pulse, this year’s parade had a respectful tone, and marchers who led the procession carried signs with the images and names of the tragedy’s victims. Next: June 2017
Photo: John W. Iwanski, CC BY-NC 2.0
#7 Parade & Holiday Event
Each year, the event begins with a wreath-laying ceremony at the Eternal Flame on Daley Plaza. Local fallen military heroes are honored, and their families are given Gold Star or Next of Kin lapel pins. A parade along State Street follows. Next: May 29, 2017
Photo: Courtesy of the City of Chicago
#8 Parade & Holiday Event
Held in Chicago’s Little Village neighborhood, the celebration of Mexican culture features carnival rides, food vendors, and entertainment. The colorful parade is broadcast on television and draws participation from corporations, businesses, and government agencies. Next: September 2017
Photo: Alex Coronell
#9 Parade & Holiday Event
Italian and American flags fly at the celebration. Following State Street from Wacker to Van Buren, this year’s parade featured more than 150 units, including floats, Italian sports cars, and bands. The theme was "Hello, Italy." Next: October 9, 2017
Photo: Courtesy of Columbus Day Parade
#10 Parade & Holiday Event
Now in its 39th year, the parade sees some 20,000 motorcyclists collecting holiday gifts for underprivileged children; it’s billed as the largest motorcycle parade in the world. To add to the festive feeling, many of the cyclists don Santa hats or deck their bikes with sparkling ornaments—“Santa” himself even rides. Next: December 4, 2016
Photo: Courtesy of Toys for Tots
#11 Parade & Holiday Event
Held on the night before New Year’s Eve, the bash typically draws some 2,000 young professionals to Union Station. Highlights include cocktails, heavy hors d’oeuvres, and dancing to a live band; there’s also an after-party at an off-site club. Proceeds benefit HighSight’s scholarship programs, and sponsors have included BMO Harris Bank Ariel Investments. Next: December 30, 2016
Photo: Courtesy of HighSight
#12 Parade & Holiday Event
Regarded by many as the unofficial kickoff to the holiday-party season, the event drew 1,100 guests to Union Station in 2015. With decor including wreaths, Christmas trees, oversize ornaments, and glittering garlands, the event offered sweet and savory chocolate dishes from 27 chefs, chocolate-makers, and caterers. (The bars also slung chocolate cocktails.) The event raised $127,000 for the foundation. Next: December 1, 2016
Photo: Stephanie Schertz/AIDS Foundation of Chicago
#13 Parade & Holiday Event
Now in its 34th year, the summertime gathering is the largest and oldest Hispanic event in Chicago—it’s also the third-largest Hispanic event in the Midwest. Held in Humboldt Park, it draws some 100,000 guests each year. It features live music on two stages, some 80 food booths, 100 arts-and-crafts vendors, carnival games, and a parade. Next: June 2017
Photo: Matthew Rubinberg
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