Chicago events calendar for May 2016. Best festivals, fun things to do, weekend street fairs, kids activities, and free entertainment in Chicago, Illinois.

Best events for 12 months
Best events for 12 months
May 2016
May 2016

Enjoy the best Chicago events, festivals, and things to do with this calendar of events.

Mileage is from the Wrigley Building in downtown Chicago, Illinois.

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Famous speakers

May 1, 2016 (begins April 28)

Chicago locations

Hear today’s leading authors, thinkers, and fashion icons speak at Style, which is a new event organized by the Chicago Humanities Festival.

Crafts fair

May 1, 2016 (begins April 29)

1 mile west

One of a Kind Show and Sale features handmade crafts by 300 artists, food, and entertainment at the Merchandise Mart. Repeats in Dec.


May 1, 2016 (begins April 30)

3 miles SW

Chicago’s best chefs serve bacon dishes and drinks for lunch and dinner at Baconfest Chicago in UIC Forum.

Elmhurst Art in the Park

May 1, 2016 (begins April 30)

17 miles west

Art in the Park is a juried show of fine art, craft, and design, which is held rain or shine at Wilder Park in Elmhurst. Free.

Touch a Truck

May 1, 2016 (11 a.m. to 2 p.m.)

25 miles north

Children can touch and explore heavy machinery & emergency vehicles and meet the drivers at Touch a Truck Family Festival, which includes food, music, and a kiddy train in Highland Park.

Animals welfare & wine

May 3, 2016 (6 to 8 p.m.)

2.5 miles north

The Humane Society’s president talks about new ways to protect animals at Wine & Wildlife, with appetizers and a cash bar in Lincoln Park Zoo, for age 18+.

Fake wedding

May 4, 2016 (7 to 9 p.m.)

0.6 miles east

Attend an emotional wedding ceremony, have a drink and appetizers (included), and dance at a reception as you check out wedding vendors in action at The Big Fake Wedding Chicago at Pinstripes.

Films about Palestine

May 5, 2016

0.5 mile SW

The Chicago Palestine Film Festival exhibits and promotes films by Palestinian directors as well as films about Palestine at the Gene Siskel Film Center.

Cinderella sequel

May 5 - 7, 2016

27.8 miles north

See what “happily ever after” means to Cinderella and her friends Rapunzel and Sleeping Beauty in Cinderella... After the Ball, which features toe-tapping music and quick witted humor at Marriott Theatre in Lincolnshire.

Improv festival

May 5 - 8, 2016

Chicago locations

Billed as the world’s longest-running festival of improvisational theater, Chicago Improv Festival includes music, song, comedy, story, and puppetry performances. Discount tickets $8.

Irving Berlin show

May 5 - 8, 2016

2.8 miles NW

Hershey Felder as Irving Berlin tells stories about the famous composer and plays his music (God Bless America, White Christmas, Puttin’ on the Ritz, etc.) at Royal George Theatre. Discount tickets $30.

Cinco de Mayo

May 5 - 8, 2016

15.4 miles SW

Viva Cinco De Mayo Festival is a new event with live music, food, arts & crafts, a carnival, and family activities outdoors at Toyota Park. Discount tickets $15 for two.

Meet the authors

May 5 - 14, 2016

13 miles north

Evanston Literary Festival includes a dozen author readings and workshops on its schedule. Free.

Lilac festival

May 5 - 15, 2016

27 miles west

Enjoy lilac-themed events at Lilac Time in Lombard, including concerts, plant sales, tours, a formal ball, a stroll through Lilacia Park, beer and wine tasting, 5K, and an art & craft fair.

The King and I

May 5 - 22, 2016

1 mile SW

The King and I is a popular musical by Rodgers & Hammerstein set in 19th-century Bangkok. This revival at the Civic Opera House recently won four Tony Awards. Discount tickets $56 to $131.

Funny musical

May 5 - 22, 2016

31.2 miles north

A Funny Thing Happened on the Way to the Forum is Stephen Sondeheim’s slapstick musical about life in ancient Rome, live at Citadel Theatre in Lake Forest. Previews April 20 & 21. Discount tickets $10 to $19.

Hazel the musical maid

May 5 - 29, 2016

18 miles west

Based on the 1960s sitcom, Hazel is a comedy about an amazing maid and the family she serves at Drury Lane Theatre in Oakbrook Terrace. Discount tickets $34.

A woman’s life revealed

May 5 - June 5,2016

3 miles NW

Mary Page Marlowe is an ordinary accountant from Ohio, but this intimate and moving play reveals a surprisingly complex personality at Steppenwolf Downstairs Theatre. Discount tickets $442.


May 5 - June 5, 2016

27.8 miles north

The musical Evita tells the story of Argentina’s former first lady, with a stunning score by Andrew Lloyd Webber including Don’t Cry for Me Argentina, at Marriott Theatre in Lincolnshire. Discount tickets $30.

Little Shop of Horrors

May 5 - June 26, 2016

3.4 miles north

Little Shop of Horrors is a comic-horror rock musical (a boy-meets-girl, plant-eats-world love story) with demented humor and goofy songs at American Blues Theater in Greenhouse Theater Center. Discount tickets $27 (May 22+).

Mel Brooks musical

May 5 - June 26, 2016

4.8 miles north

Based on a classic film, The Producers is a Tony-winning musical comedy about two con artists who produce a show at Mercury Theater. Discount tickets $31.

Blue Man show

May 5 - Oct. 2, 2016

4.5 miles north

Blue Man Group puts on an exciting show that combines comedy, theater, music, and special effects at Briar Street Theatre. Discount tickets $43.

Bach festival

May 6, 2016 (begins April 22)

Chicago locations

Bach Week Festival is a series of four classical music concerts in North Chicago and Evanston held on April 22, 24, and May 6.

Adult scavenger hunt at the zoo

May 6, 2016 (6 to 10 p.m.)

2.5 miles north

Form a team with your friends to solve clues and compete for prizes at Lincoln Park Zoo Challenge, with a free beer at the after party. Costumes welcome.

Music festival in Edison Park

May 6 - 8, 2016

13 miles NW

Hear dozens of bands perform at Off the Trax Music Fest [formely North by Northwest] in four venues with a $3 cover charge per show.


May 6 - 8, 2016

21 miles NW

Step back in time to the decadent Kit Kat Klub of prewar Germany as colorful singers serenade you at Cabaret in Des Plaines. Discount tickets $15.

Adult variety show

May 6 - 28, 2016

7 miles north

Kiss Kiss Cabaret is a fun mix of burlesque, off-color comedy, music, magic, and variety acts at Uptown Underground. Reviews.

Discount tickets $4 to $13.

Dinner cruise

May 6 & 15, 2016

1 mile east

Enjoy a three-course meal with a champagne cocktail and views of the Chicago skyline aboard the luxurious Odyssey, leaving Navy Pier.

Discount tickets $78 to $111.

Smart, sexy drama

May 6 - June 12, 2016

3.1 miles NW

A salesman who hires an escort for New Year’s gets more than he bargained for in Twisted Knots, premiering at Royal George Theatre.

Discount tickets $8 to $15.

Intelligent comedy

May 6 - June 12, 2016

16 miles north

Imagine putting Thomas Jefferson, Charles Dickens, and Leo Tolstoy in the same room. They debate the meaning of life in Discord, a whip-smart comedy by the writer for Bill Maher at Skokie’s Northlight Theatre. Discount tickets $25.

Dating comedy

May 6 - July 31, 2016

2.1 miles north

Based on actual online-dating conversations, #DateMe: An OKCupid Experiment is a comic mix of original music, improvisation, and multimedia elements at Up Comedy Club. Discount tickets $16.

Polish parade

May 7, 2016 (11:30 a.m.)

1 mile south

Polish Constitution Day Parade celebrates ratification of the Polish constitution in 1791 and is billed as the biggest Polish parade outside Poland. It’s on State Street from Lake to Van Buren. Free.

Chicago Beer Classic

May 7, 2016

2 miles south

Chicago Beer Classic [formerly American Beer Classic] has hundreds of beers, food vendors, and seminars on the grass at Soldier Field.

Kids’ kite festival

May 7, 2016 (10 a.m. to 4 p.m.)

6 miles north

Children can fly free paper kites, run around outdoors, get their faces painted, and do crafts at Chicago Kids and Kites Festival on Cricket Hill near N Lake Shore Dr. & Montrose Ave. Free.

Hobbies on display

May 7, 2016

8.2 miles NW

Share creative hobbies and ingenious do-it-yourself projects at the Chicago Northside Mini Maker Faire at Carl Schurz High School. Free.

Small art fair

May 7, 2016

16 miles NW

Arts & Crafts Adventure is a friendly juried show at Hodges Park in Park Ridge. Repeats Sept. Free.

Game of Thrones parody

May 7 - July 2, 2016 (7 p.m. Saturdays)

5 miles north

See your favorite characters, plots, and battles of five seasons crammed into a single hour of comedy at A Swarm of Spoilers by Under the Gun Theater.

Discount tickets $13.

Comedy dinner

May 7 - Oct. 19, 2016

4.5 miles north

We Gotta Bingo [sound] delivers corny, bawdy, slapstick humor, lasagna, bread, and salad, as you participate in a bingo game between rival parishes at Chicago Theater Works. Discount tickets $20 to $40.

Mother’s Day restaurants

May 8, 2016

Chicago locations

OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Mother’s Day. Zagat recommends a dozen restaurants for brunch.

Mother’s Day run/walk

May 8, 2016 (8 a.m.)

0.9 miles SW

Join the 5K/10K Komen Chicagoland Area Race for the Cure at Butler Field to help cure breast cancer.

Mother’s Day cruise

May 8, 2016

1 mile east

Take a brunch or dinner Chicago Mother’s Day Cruise from Navy Pier.

Mother’s Day salsa dance

May 8, 2016 (12:30 to 1:45 p.m.)

6.4 miles NW

Mother’s Day Salsa Dance Party is a family-friendly beginner dance class for 45 minutes, followed by open dancing and light refreshments at Duet Dance Studio.

Mozart on Mother’s Day

May 8, 2016 (3 p.m.)

7 miles north

Enjoy an afternoon of culture, coffee and cake as you hear instrumental and vocal German chamber music at Mozart für Mutti in the ballroom at Dank Haus German American Cultural Center.

Mother’s Day house walk

May 8, 2016

12 miles north

Tour six remarkable homes plus the historic Charles Gates Dawes House on the annual Mother’s Day Housewalk in North Evanston.

Mother’s Day Jazz Brunch

May 8, 2016 (11 a.m. to 2 p.m.)

13.2 miles north

Enjoy the brunch buffet, Mimosas & Bloody Marys, and jazz by the Sean Van Dril Trio at Mother’s Day Jazz Brunch at The Crystal Ballroom & Lounge in Evanston.

Mother’s Day Brunch - zoo

May 8, 2016

14 miles SW

Make a reservation for a champagne Mother’s Day Brunch at the Brookfield Zoo at 11 a.m. or 1:30 p.m.

Mother’s Day garden brunch

May 8, 2016 (9 a.m.)

24 miles north

Treat Mom to an elegant Mother’s Day Brunch followed by a walk through the Chicago Botanic Garden in Glencoe.

Comedy brunch

May 8 - Sept. 25, 2016

2.3 miles north

Second City’s Sunday Bloody Mary Sunday begins with a delicious brunch including limitless Bloody Marys and mimosas, followed by an improv comedy show at UP Comedy Club.

Discount tickets $40.

Five minutes of science

May 10, 2016 (7:30 to 8:30 p.m.)

1.8 miles north

Register to hear five experts speak for five minutes about interesting science subjects like dinosaurs at (En)Lightning Talks Chicago at Chicago History Museum.

Tony-winning musical

May 10 - 15, 2016

0.7 miles SW

John O’Hurley stars in show-business musical Chicago, which has sizzling songs, seductive dance numbers, and a powerful story at Cadillac Palace Theatre. Discount tickets $25 to $69.

Rocking dinner show

May 10 - 31, 2016 (7:30 p.m. Tuesdays)

0.8 miles NW

Hear hits from the rock and roll era at Rock Baby Rock featuring a band and vocalists with optional dinner at Hard Rock Cafe. Discount tickets $15.

Hit musical for adults

May 10 - June 5, 2016

0.9 miles north

The Disenchanted Disney princesses sing, dance, and poke fun at pop culture in their hilariously subversive renegade show at Broadway Playhouse. Discount tickets $59.

Book expo

May 11 - 13, 2016

3 miles south

Book Expo America includes 1000 exhibitors, author lectures and autographing events, and publishing-industry sessions at McCormick Place.

Cinderella ballet

May 11 - 22, 2016

1 mile south

The Joffrey Ballet presents the magical and romantic fairy tale Cinderella at Auditorium Theatre.

Discount tickets $62.

Magic show

May 11 - July 27, 2016 (8 p.m. Wednesdays)

3.3 miles north

The Magic Cabaret entertains with mind-boggling sleight of hand and audience participation in small Greenhouse Theater Center. Discount tickets $10.

Art festival in homes

May 12 - 22, 2016

Chicago locations

Chicago Home Theater Festival transforms 10 homes into neighborhood sites for art, performances, and films. It has a pre-party and a closing-night event.

Magic lounge

May 12 - June 30, 2016 (8 p.m.)

7 miles north

Chicago Magic Lounge is an old-school magic show with close-up magic, bar magic, table-hopping magicians, and main stage acts at beautiful Uptown Underground. Discount tickets $13.

Museum party

May 13, 2016 (9 p.m.)

1 mile south

Mix and mingle, visit the bar, eat appetizers, hear DJ music, and see a show at After Dark in the Modern Wing of the Art Institute of Chicago for age 21+.

Urban arts festival

May 13, 2016

1 mile south

Manifest is a full day of student art, poetry, music, and culture in and around Columbia College. Free.

Fashion show

May 13, 2016

5 miles west

Fashion 2016 presents designs by students of the School of the Art Institute of Chicago at Garfield Park Conservatory.

Creativity expo

May 13 - 15, 2016

0.4 miles south

Hear experts speak about art, fashion, film, food, and music at Lake FX Summit + Expo (formerly called Chicago Music/Film/Fashion+ Summit) at Chicago Cultural Center. Free.

Funny dinner show

May 13 - July 29, 2016 (also April)

5.8 miles north

Colorful characters gather in an Irish town to mourn the death of a local at Flanagan’s Wake, with stories, sing alongs, and a free buffet (except 10 p.m.) at Chicago Theater Works. Discount tickets $29.


May 14, 2016 (2 & 7:30 p.m.)

0.5 miles south

Ballet Chicago presents Take Flight, with two works by George Balanchine and its resident choreographer at Harris Theater in Millennium Park. Discount tickets $13.

Science talks

May 14, 2016

1 mile west

Hear experts talk about a dozen topics, such as urban wildlife, sleep cycles, ocean research, and 3D printing at Chicago Science Fest at the Merchandise Mart.

Pop music party

May 14, 2016 (2 p.m.)

7 miles north

Watch Europe’s pop singing competition live from Stockholm at Eurovision Song Contest Viewing Party at Dank Haus. Free, with beer and snacks for sale.

Zombie Pub Crawl

May 14, 2016 (2 to 10 p.m.)

8 miles north

Zombie Pub Crawl for adults begins at the pH Comedy Theater in Andersonville.

Beer festival

May 14, 2016

33 miles NW

A ticket to Ballpark Brew Fest includes 25 samples of beer (3 ounces) from 50 breweries, with food for sale at Schaumburg Boomers Stadium.

Basketball tournament

May 14 - 15, 2016 (11 a.m.)

5.3 miles NW

Power of Play is a charity 5-on-5 basketball tournament with skills competitions and live entertainment for ages 13 to 17 on Saturday, and ages 18+ on Sunday, at Windy City Fieldhouse.

Gluten-free expo

May 14 - 15, 2016

28 miles NW

Sample and purchase products from 100 vendors and attend classes at Gluten Free & Allergen Friendly Expo at the Schaumburg Convention Center.

Retro musical

May 14 - 29, 2016 (weekends)

5.8 miles north

Set in the 1960s, Chicago Doo-Wop Dreams tells the story of local boys trying to sing their way to fame and fortune, weaving together improvised songs, covers of classic pop, and original tunes accompanied by a four-piece band at MCL Chicago. Discount tickets $11.

Wine tasting

May 15, 2016

9 miles north

Andersonville Wine Walk begins at the Swedish American Museum. You choose a north or south route and visit 11 retail shops serving wine to adults.

Elmhurst Museum Day

May 15, 2016 (1 to 5 p.m.)

19 miles west

Elmhurst Museum Day includes the museums of art, history, and minerals plus a free trolley that connects them all. Free.

Rhubarb Festival

May 15, 2016

62 miles south

The Rhubarb Festival features rhubarb and strawberry pies and jams, a baking contest, kids’ games, and live music at Kankakee County Museum. Free entry.

Classic comedy

May 15 - June 5, 2016

20.1 miles north

Both Spencer Tracy and Steve Martin have played the Father of the Bride on film. Now see this comedy about matrimonial mayhem live onstage at Oil Lamp Theater in Glenview. Discount tickets $18 (2 left).

Beer at the conservatory

May 19, 2016 (6:30 p.m., VIP 5:30)

5 miles west

Enjoy craft beer and small plates at Beer under Glass indoors and outdoors at Garfield Park Conservatory.

Craft beer week

May 19 - 29, 2016

Chicago locations

Chicago Craft Beer Week features hundreds of craft beer events in the greater Chicago area, from special $4 tastings of rare beers to beer dinners. It’s sponsored by the Illinois Craft Brewers Guild.

Art fair indoors & outdoors

May 20 - 21, 2016

10 miles west

What’s Blooming on Harrison is indoors Friday evening and outdoors Saturday, with arts and crafts, artist demos, live music, and dance in Oak Park. Free.


May 20 - 22, 2016

5 miles NW

Mayfest [sound] features bands in a giant tent, festival food, pretzels, and beer at 3100 N Ashland Ave. Saturday includes a kids’ day from 10 a.m. to 2 p.m. (Don’t confuse with Maifest on June 2 - 5, 2016.)

Anime convention

May 20 - 22, 2016

16 mile NW

Anime Central (ACen) is billed as the largest Midwest anime, manga, and Japanese popular culture convention, at the Hyatt Regency O’Hare and the convention center in Rosemont.

Stamp show

May 20 - 22, 2016

23.9 miles NW

See postage stamp exhibits and shop from 50 dealers at Compex in Arlington Heights. Free.

Film festival

May 20 - 26, 2016

6 miles north

Billed as the first film festival to be created and curated entirely by film critics, Chicago Critics Film Festival is held at the Music Box Theatre.

Architectural tour

May 21, 2016

Greater Chicago area

Tour innovative homes and buildings designed by Frank Lloyd Wright on the Wright Plus walk.

Food truck evening

May 21, 2016 (6:30 to 10:30 p.m.)

2.5 miles north

Food Truck Social features 30 trucks selling food and beverages, activities, live music, and an opportunity to wander Lincoln Park Zoo after hours.

Walk with the dogs

May 21, 2016 (9 a.m., register 7 to 9)

2.5 miles south

Walk a 5K along the lakefront with your dog during Bark in the Park, followed by games and activities on the green near Soldier Field

Baseball pub crawl

May 21, 2016

5 miles north

Cover Your Bases is a baseball-themed pub crawl. You get a T-shirt printed with a baseball field, and then cover the bases with stickers from the bars you visit. Use promo code “winning” or get discount tickets for $12.

Zombie Prom

May 21, 2016 (8 p.m.)

6 miles north

Dress as a zombie or get a makeover for $10, and then join the undead for contests, a live band, and a buffet at the Chicago Zombie Prom at the Cubby Bear.

Wine tasting

May 21 - 22, 2016

4 miles north

Taste 80 wines at Lincoln Park Wine Festival, which has tented wine and food pavilions, live music, and crafts at Jonquil Playlot Park. Discount tickets $40 at Groupon and LivingSocial.

Riverside Arts Weekend

May 21 - 22, 2016

12 miles SW

Riverside Arts Weekend (RAW) has a juried arts fair, fashion show, outdoor theater, and jazz & folk music at Guthrie Park in Riverside. Free.

Festival of cultures

May 21 - 22, 2016

15 miles NW

Experience ethnic folk music and dance, exotic food, unique arts and crafts, international children’s games, beer tasting, a bazaar, and cultural exhibits at the Skokie Festival of Cultures in Oakton Park. Free.

Oak Brook art fair

May 21 - 22, 2016

19 miles west

Spring Art Festival features art, artists in action, and music in Oak Brook. Repeats Sept. Free.

Japanese children’s festival

May 21 - 22, 2016

24 miles north

Learn about children’s celebrations in Japan at Malott Japanese Garden Children’s Festival. Listen to koto harps and shakuhachi flutes, hear folktales, and watch a tea ceremony at the Chicago Botanic Garden in Glencoe. Free except parking.

Home show in Wheaton

May 21 - 22, 2016

27 miles west

Find renovation help at The DuPage County Home Improvement & Landscaping Expo at DuPage County Fairgrounds in Wheaton.

Walking tour & brunch

May 21 & 28, 2016 (9:30 a.m. Sat.)

0.4 miles SE

Pedway Brunch Tour is a 3-hour excursion starting at the Radisson Blu Hotel and following the city’s heated pedestrian walkway, with an included buffet brunch. Discount tickets $35.

Doggie dash

May 22, 2016

37 miles NW

Dash for the Dogs is a 5K run and a 1-mile family walk, followed by awards and food to benefit Animal House Shelter in Barrington.

Rock musical

May 25 - July 3, 2016

26 miles NW

Theatremania calls Rent a “passionate, exuberant, uplifting, and joyous” story of young New York artists living in the shadow of AIDS, at Metropolis Performing Arts Centre in Arlington Heights. Discount tickets $19.

Wine at Botanic Garden

May 26, 2016

24 miles north

Try wines from 11 wineries and light fare at Grapevines & Wines in McGinley Pavilion at the Chicago Botanic Garden in Glencoe.


May 27 - 29, 2016

23 miles west

Billed as the state’s largest BBQ competition, Red, White, and Bar-B-Q has live music, craft vendors, a carnival, beer tent, and barbeque in Westmont. Free.

Big music festival near Peoria

May 27 - 29, 2016

144 miles SW

Summer Camp Music Festival typically attracts 20,000 fans watching 100 bands on 7 stages in Chillicothe.

Irish festival

May 27 - 30, 2016

26 miles south

Chicago Gaelic Park Irish Fest offers music, theater, storytelling, dancing, and family entertainment on six stages in Oak Forest.

Cirque + symphony

May 28, 2016 (7:30 p.m.)

0.5 miles south

Watch aerial flyers, acrobats, contortionists, dancers, jugglers, and strongmen move to music when Chicago Philharmonic & Cirque de la Symphonie perform together at Harris Theater in Millennium Park. Discount tickets $27.

Memorial Day Parade

May 28, 2016 (noon)

0.5 mile SW

A wreath laying ceremony is 11 a.m. at the Eternal Flame on Daley Plaza. The Memorial Day Parade at noon has high-school marching bands, drum and bugle corps, veterans’ groups, and active duty military on State St. from Lake to Van Buren. Free.

Wine festival

May 28, 2016

11 miles west

Sample 150 wines from 15 local wineries and taste artisan foods at Uncork Illinois in Oak Park.

Belmont-Sheffield music fest

May 28 - 29, 2016 (12 to 10 p.m.)

5 miles north

Celebrate Memorial Day weekend with local bands, food, drink, and street vendors at the Belmont-Sheffield Music Festival on N. Sheffield from Belmont to Roscoe. Donation.

Zombie, horror, sci-fi convention

May 28 - 29, 2016

17 miles NW

Zombie lovers unite at Walker Stalker Con for panels, celebrities, vendors, and a costume party at the convention center in Rosemont. Discount tickets $10.

Art fair in Barrington

May 28 - 29, 2016

38 miles NW

Barrington Art Festival features 130 juried artists, live music, food, and children’s activities. Free.

St. Charles art show

May 28 - 29, 2016

45 miles west

St. Charles Fine Art Show is billed as an award-winning show by 100 juried artists with live music in downtown St. Charles. Free.

Dinner cruise

May 29, 2016 (7 p.m.)

1 mile east

Enjoy a buffet meal, DJ dance music, and views of the Chicago skyline aboard the Spirit of Chicago Dinner Cruise, leaving Navy Pier.

Discount tickets $72.

Spectacular bike ride

May 29, 2016

1 mile south

Register to ride your bike on 15-mile Lake Shore Dr. when it closes to vehicles during Bike the Drive, and attend an after festival until noon at Butler Field.
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© May 2016 calendar of events in Chicago, IL. Best events, fairs, festivals, and things to do in Chicago, Illinois.