Chicago events calendar for May 2017. 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 2017
May 2017

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

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

Latino film festival

May 1 - 4, 2017 (begins April 20)

Chicago locations

See 100+ films from Latin America, Brazil, Spain, and Portugal during the Chicago Latino Film Festival at AMC River East 21 theaters and venue partners throughout Chicagoland.

Films about Palestine

May 1 - 4, 2017 (begins April 15)

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.

Meet the authors

May 1 - 11, 2017 (begins April 29)

13 miles north

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


May 1 - Aug. 31, 2017

multiple locations

These discount ticket prices include all taxes and fees.

Hilarious play

May 3 - 28, 2017 (also April)

31 miles north

Winner of a best play Tony Award, Vanya and Sonia and Masha and Spike is a zany farce about a dysfunctional family with themes and characters from Chekhov in Lake Forest. Discount weekday tickets $6 to $18.

Magic Cabaret

May 3 - Aug. 30, 2017 (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 $13.

Joffrey Ballet

May 4 - 7, 2017 (begins April 26)

1 mile south

World-famous Joffrey Ballet performs Global Visionaries, three works by choreographers from Sweden, Russia, and the Netherlands at Auditorium Theatre. Discount tickets $43 to $80.

Magic lounge

May 4 - June 29, 2017 (from March)

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 Uptown Underground for age 21+. Discount tickets $12 - $14.

Dinner cruise

May 5, 2017 (8 p.m.)

1 mile east

Enjoy a three-course meal aboard the luxurious Odyssey as you cruise past the Chicago skyline, departing from Navy Pier. Discount tickets $86.

My Fair Lady

May 5 - 6, 2017 (also April)

1 mile SW

Lerner & Loewe wrote My Fair Lady, a musical about a Cockney woman who takes speech lessons on a bet to see if she can pass as a lady, at the Civic Opera House. Discount tickets $43 to $131.

Small press festival

May 5 - 6, 2017

2.5 miles west

A zine is a cheap, self-published, underground publication. Chicago Zine Fest offers panel discussions Friday, plus exhibitions by 200 writers, artists, and publishers Saturday on the Near West Side. Free.

Bach festival

May 5 & 7, 2017 (begins April 28)

Chicago locations

Bach Week Festival is a series of three classical music concerts in North Chicago and Evanston on April 28, May 5, and May 7.

Cinco de Mayo

May 5 - 7, 2017

15.4 miles SW

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

Party cruise

May 5 - 29, 2017 (also April)

0.7 miles east

A Booze Cruise aboard the Anita Dee II offers amazing views from the top deck, dancing, and a cash bar, departing from 200 N Breakwater Access for age 21+. Discount tickets $25.

Polish parade

May 6, 2017 (11:30 a.m.)

1.3 mile south

Polish Constitution Day Parade celebrates ratification of the Polish constitution in 1791 and is billed as the biggest Polish parade outside Poland, on S. Columbus Drive (from Balbo Street to Monroe Street). Free.

Chicago Beer Classic

May 6, 2017

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 6, 2017

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 6, 2017

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.

Beer festival

May 6, 2017

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.

Elmhurst Art in the Park

May 6 - 7, 2017

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.

Fitness expo

May 6 - 7, 2017

17 miles NW

See martial arts, power-lifting, strongman, and wrestling competitions plus 200 vendors of fitness products and services at TheFitExpo Chicago at the Rosemont convention center.

Lilac festival

May 6 - 21, 2017

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 Wiz

May 6 - June 8, 2017 (also April)

3.8 miles north

Dorothy and her companions sing and dance to rock, gospel, and soul in The Wiz as they travel though a gritty African-American land of Oz at the Apollo Theater in Lincoln Park. Discount tickets $10.

Wine at Botanic Garden

May 11, 2017

24 miles north

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

Dinner cruise

May 12, 2017 (boarding 7 p.m.)

1 mile east

Enjoy a buffet meal aboard the Spirit of Chicago Dinner Cruise, with views of the Chicago skyline and DJ dance music, departing from Navy Pier. Discount tickets $74.

Urban arts festival

May 12, 2017

1 mile south

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

Film festival

May 12 - 18, 2017

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.

Food truck evening

May 13, 2017

2.5 miles north

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

Baseball pub crawl

May 13, 2017

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.

Small art fair

May 13, 2017 (9 a.m. to 5 p.m.)

16 miles NW

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

Art festival in homes

May 13 - 29, 2017

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.

Mother’s Day restaurants

May 14, 2017

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 cruise

May 14, 2017

1 mile east

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

Mother’s Day salsa dance

May 14, 2017

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.

Mother’s Day run/walk

May 14, 2017 (9 a.m.)

6.8 miles north

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

Mother’s Day house walk

May 14, 2017

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 Brunch - zoo

May 14, 2017

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 14, 2017

24 miles north

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

Beer at the conservatory

May 18, 2017

5 miles west

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

Science talks

May 18 - 20, 2017

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.

Craft beer week

May 18 - 25, 2017

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

May 19 - 20, 2017

10 miles west

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


May 19 - 21, 2017

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 19 - 21, 2017

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 19 - 21, 2017

23.9 miles NW

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

Architectural tour

May 20, 2017

Greater Chicago area

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

Running music festival

May 20, 2017 (evening)

2.7 miles south

Night Nation Run is a 5K run/walk to multiple stages that have EDM dance music, lights, lasers, and glowsticks at Soldier Field. Discount tickets $30.

Wine tasting

May 20 - 21, 2017

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 20 - 21, 2017

12 miles SW

Riverside Arts Weekend (RAW) has a juried arts fair with live music, a children’s corner, and a food court at Guthrie Park in Riverside. Free.

Festival of cultures

May 20 - 21, 2017

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 20 - 21, 2017

19 miles west

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

Japanese children’s festival

May 20 - 21, 2017

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.

Walk with the dogs

May 21, 2017 (10 a.m. to 2 p.m.)

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.

Wine tasting

May 21, 2017 (2 - 5 p.m.)

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 21, 2017

19 miles west

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

Doggie dash

May 21, 2017

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.

Rhubarb Festival

May 21, 2017 (10 a.m. to 4 p.m.)

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.

BBQ tasting

May 25, 2017 (5:30 to 9 p.m.)

0.5 miles south

A ticket to Smokin’ Pork In The Park gets you unlimited baby back ribs from competitors at the Park Grill.

Rock musical: Hair

May 25 - July 1, 2017

26 miles NW

Tony Award winner Hair features the music, culture, and controversy of hippies who opposed the Vietnam War at Metropolis Performing Arts Centre in Arlington Heights. Discount tickets $19.


May 26 - 28, 2017

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 barbecue in Westmont. Free.

Big music festival near Peoria

May 26 - 28, 2017

144 miles SW

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

Irish festival

May 26 - 29, 2017

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 27, 2017

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.

Belmont-Sheffield music fest

May 27 - 28, 2017 (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 Avenue (from Belmont to Roscoe). Donation.

Art fair in Barrington

May 27 - 28, 2017

38 miles NW

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

St. Charles art show

May 27 - 28, 2017

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.

Memorial Day cruise

May 28, 2017 (boarding 11:30 p.m.)

1 mile east

Wear white to the Pier Pressure party cruise for three hours of skyline views, DJ dance music, and a pricey bar, departing from Navy Pier. Discount tickets $19.

Spectacular bike ride

May 28, 2017

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.

Underground film festival

May 31 - June 4, 2017

7 miles NW

Chicago Underground Film Festival (CUFF) shows independent, experimental, and documentary films from around the world at the Logan Theatre, followed by nearby after-parties.

Basketball tournament

May 2017 (undated)

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.

Zombie Prom

May 2017 (undated)

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 [sound] at the Cubby Bear.

Pop music party

May 2017 (undated)

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.

Beer festival

May 2017 (undated)

8 miles north

Welles Park Craft Beer Fest (WPCBF) includes craft beer, entertainment, and food for sale in beautiful Welles Park for age 21+.
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© May 2017 calendar of events in Chicago, IL. Best events, fairs, festivals, and things to do in Chicago, Illinois. ord-05