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

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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.

Famous speakers

May 1, 2016 (begins April 28)

Chicago locations

Hear today’s leading authors, thinkers, and fashion icons speak at the Spring Festival 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.

Films about Palestine

May 1 & 5, 2016 (begins April 16)

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.

Lilac festival

May 1 - 15, 2016 (begins April 30)

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.

Improv festival

May 2 - 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.

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.


May 4 - 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.

Meet the authors

May 4 - 14, 2016

13 miles north

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

Cinco de Mayo

May 5 - 8, 2016

15.4 miles SW

Viva Cinco De Mayo Festival has live music, food, arts & crafts, a carnival, and family activities outdoors at Toyota Park.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Basketball tournament

May 14, 2016 (12:30 p.m.)

5.3 miles NW

Power of Play is a charity 5-on-5 basketball tournament with skills competitions and live entertainment, with a youth tournament (ages 13 to 17) and adult tournament at Windy City Fieldhouse.

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.

Wine tasting

May 15, 2016 (SOLD OUT)

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.

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. [They say $75 tickets are available today at the door.]

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.


May 20 - 22, 2016

5 miles NW

Mayfest 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.

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

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.

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.

Art fair

May 21, 2016

10 miles west

What’s Blooming on Harrison offers arts and crafts, artist demos, live music, and dance in Oak Park. Free.

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.

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.

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.

Wine at Botanic Garden

May 26, 2016 (6 to 8 p.m.)

24 miles north

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

Steampunk party

May 27, 2016 (7 p.m. to midnight)

6.7 miles NW

Electric Moulin Mansion promises “a spectacular night filled with exotic shows, world-class musicians, and colossal artwork” plus cocktails at Stan Mansion.


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.

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.

Beer festival

May 28, 2016 (1 p.m., VIP noon)

8 miles north

Welles Park Craft Beer Fest (WPCBF) includes craft beer, entertainment, and food for sale in beautiful Welles Park for age 21+.

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.

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.

Spectacular bike ride

May 29, 2016

1 mile south

Register to ride your bike on 15-mile Lake Shore Drive when it closes to vehicles during Bike the Drive, and join the 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.