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.

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

21 miles north

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

Music festival in Edison Park

May 6 - 8, 2016

13 miles NW

Hear dozens of bands perform at North by Northwest Hwy Music Fest in four venues with $3 cover charge.

Polish parade

May 7, 2016

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 Dearborn Street from Lake to Van Buren. 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.

Lilac festival

May 7 - 15, 2015 (uncertain)

27 miles west

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

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

0.9 miles SW

Join the 5K/10K Komen Chicagoland 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 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 garden brunch

May 8, 2016

24 miles north

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

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.

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.

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

19 miles west

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

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. Saturday is kids’ day. Sunday is a pet pageant and expo. At 3100 N Ashland Ave. (Don’t confuse with Maifest on June 2, 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.

Architectural tour

May 21, 2016

Greater Chicago area

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

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.

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.

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

24 miles north

Try wines from 10 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 BBQ has live music, craft vendors, a carnival, beer tent, and barbeque in Westmont. Free.

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.

Memorial Day Parade

May 28, 2016

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.

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 Dr. when it closes to vehicles during Bike the Drive, and attend an after festival until noon at Butler Field.

Film festival

May 2016 (undated)

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.

Cinco de Mayo - bar crawl

May 2016 (undated)

0.5 miles NW

Cinco de Mayo Cantina Crawl includes live mariachis, games, contests, food specials, and a free tequila cocktail at four bars in River North.

Kids’ kite festival

May 2016 (undated)

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.

Zombie Pub Crawl

May 2016 (undated)

8 miles north

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

Beer festival

May 2016 (undated)

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.

Art festival in homes

May 2016 (undated)

Chicago locations

Chicago Home Theater Festival transforms 15 homes into neighborhood sites for art, performances, and films. It has a pre-party and a closing-night event.

Stages, Sights & Sounds

May 2016 (undated)

Chicago locations

Stages, Sights & Sounds is a global performance festival that appeals to families and includes original work from Europe and Canada. Chicago Humanities Festival is a similar event for adults in the fall.

Fashion show

May 2016 (undated)

0.5 mile south

Fashion 2016 presents designs by students of the School of the Art Institute of Chicago at Millennium Park’s Chase Promenade.

American Beer Classic

May 2016 (undated)

2 miles south

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

Baseball pub crawl

May 2016 (undated)

5 miles north

Cover Your Bases is a baseball themed pub crawl. You get a T-shirt printed with a baseball field, and cover the bases with stickers from the bars you visit.

Flower show

May 2016 (undated)

5 miles west

The Spring Flower Show at Garfield Park Conservatory includes kids’ activities called Fiddleheads. Free.

Meet the authors

May 2016 (undated)

13 miles north

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

Beer at the conservatory

May 2016 (undated)

5 miles west

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

Craft beer week

May 2016 (undated)

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.

Beer & music fest

May 2016 (undated)

0.5 miles west

Local Brews Local Grooves combines craft beer from 17 breweries with live music at House of Blues, $13. Tasting wristband is an additional $15 at the door.

Wine tasting

May 2016 (undated)

0.8 miles north

Taste domestic and imported wines with hors d’oeuvres at Around the World in 80 Sips at the Museum of Contemporary Art.

Urban arts festival

May 2016 (undated)

1 mile south

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

Wine tasting

May 2016 (undated)

1.5 miles SW

Choose from 250 wines to taste at Wine Riot in the Great Hall at Union Station, and track your favorites on the free mobile app. Repeats Oct.

Riverside Arts Weekend

May 2016 (undated)

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.

Oak Brook art fair

May 2016 (undated)

19 miles west

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

Rhubarb Festival

May 2016 (undated)

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.

Pop music party

May 2016 (undated)

7 miles north

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

Hawaiian pub crawl

May 2016 (undated)

17 miles NW

Everyone Gets Leis has bands, bar specials, contests, and fireworks in MB Financial Park, Rosemont.

Gospel music festival

May 2016 (undated)

0.5 miles south

Hear gospel choirs and soloists at the Chicago Gospel Music Festival in Millennium Park. Free.

Vegetarian parade

May 2016 (undated)

1.3 miles south

The Chicago Veggie Pride Parade includes guest speakers and a costume contest in Grant Park. Free.

Wine festival

May 2016 (undated)

11 miles west

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

Wine tasting

May 2016 (undated)

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.

Mozart on Mother’s Day

May 2016 (undated)

7 miles north

Enjoy a selection of arias and scenes from works by Mozart at affordable Mozart für Mutti in the ballroom at Dank Haus German American Cultural Center.

Belmont-Sheffield music fest

May 2016 (undated)

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.
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© May 2016 calendar of events in Chicago, IL. Best events, fairs, festivals, and things to do in Chicago, Illinois.