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, South America, Spain, Portugal, and the U.S. during the Chicago Latino Film Festival at AMC River East 21 theaters and venue partners throughout Chicagoland.

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.

Short play festival

May 2 - 3, 2017 (8 p.m.)

0.5 miles west

See dozens of locally written short plays at The One Minute Play Festival at The Den Theatre.

Parody of “Hamilton”

May 2 - 14, 2017 (also April)

3.1 miles NW

Spamilton is a “smart, silly, and often convulsively funny” parody with “surreal Broadway musical mash-ups” [New York Times] at Royal George Theatre. Discount tickets $49 to $65.

Films about Palestine

May 3 - 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.

Funny 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 tickets $8 to $19.

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.

Mary Poppins

May 4 - 28, 2017 (also April)

4.8 miles north

Magical nanny Mary Poppins sings catchy tunes and works her charms on an English family at Mercury Theater. Discount tickets $23 to $55.

Motherhood show

May 4 - June 11, 2017 (also April)

20.1 miles north

Motherhood Out Loud is “ joyous, moving, hilarious, and altogether thrilling” as it celebrates deeply personal family truths at Oil Lamp Theater in Glenview. Discount tickets $18.

Magic lounge

May 4 - June 29, 2017 (also April)

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.

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 $98.

Male cabaret

May 5, 2017 (8 p.m.)

7 miles north

Boy Toy’s Pocket Cabaret features a cast of both male and female performers who mix up burlesque-style acts, pole art, belly dancing, and acrobatics at Uptown Underground. Discount tickets $10.

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. Discount tickets $15 for two people.

Dating comedy

May 5 - 26, 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 $12 to $16.


May 6, 2017 (2 and 7:30 p.m.)

0.5 miles south

Ballet Chicago celebrates its 20th anniversary with 4 works, including a world premiere, at Harris Theater in Millennium Park. Discount tickets $13 to $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 for age 21+.

Kids’ kite festival

May 6, 2017 (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 at Cricket Hill in Lincoln Park. 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 (2 p.m., VIP 1 p.m.)

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 Wilder Park is a juried show of fine art, craft, and design, which is held rain or shine 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.

Discount tickets $15.

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.

Comedy dinner show

May 6 - 28, 2017 (also April)

5.8 miles north

You’re invited to fictitious Tony ‘n Tina’s Wedding at Resurrection Church, followed by a real Italian dinner at Chicago Theater Works, with plenty of comedy improv and audience interaction. Discount tickets $59 to $69.

Stories about motherhood

May 7, 2017 (2 p.m.)

5 miles north

Listen To Your Mother celebrates and validates motherhood with a dozen touching and humorous short stories at Athenaeum Theatre.

My Fair Lady

May 4 - 21, 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 $39 to $71.

Magic Cabaret

May 10 - 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.

Disney’s Aladdin

May 10 - Sept. 10, 2017

0.7 miles SW

Aladdin is a magical love story with “unforgettable beauty, magic, comedy and breathtaking spectacle” at Cadillac Palace Theatre. Discount tickets $62 to $78.

Wine in the garden

May 11, 2017 (6 to 8 p.m.)

24 miles north

Try wines from eight wineries and light fare at Grapevines & Wines in McGinley Pavilion at the Chicago Botanic Garden in Glencoe for age 21+.

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 trucks at the zoo

May 13, 2017 (6:30 to 9:30 p.m.)

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 (12:05 p.m.)

5 miles north

TBOX Baseball Bar Crawl is a baseball-themed pub crawl starting at Murphy’s Bleachers. You get a T-shirt printed with a baseball field, and then cover the bases with stickers from bars you visit. Discount tickets $12.

Pop music party

May 13, 2017 (1 to 5 p.m.)

7 miles north

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


May 13, 2017 (7:30 p.m.)

15 miles SW

Watch Chicago Fire play the Seattle Sounders in a home game at Toyota Park. Discount tickets $49.

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.

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 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 to 5 p.m.)

12 miles north

Tour five historic homes, two coach houses, and Levere Memorial Temple 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.

Mother’s Day garden brunch

May 14, 2017 (SOLD OUT)

24 miles north

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

Party in the planetarium

May 18, 2017 (6:30 to 10:30 p.m.)

2.5 miles SE

Adler After Dark: Planetary Prom is a dance party “with hands-on programs, theater shows, and special talks on current planetary missions” at Adler Planetarium for age 21+.

Beer at the conservatory

May 18, 2017 (5:30 to 9:30 p.m.)

5 miles west

Enjoy craft beer and food trucks at Beer under Glass indoors and outdoors at Garfield Park Conservatory.

Science talks

May 18 - 20, 2017

1 mile west

Hear eight experts talk about the science of cannabis, sleep research, gene therapy, prosthetics, and more at Chicago Science Fest, with exhibits about solar power, electric cars, and edible bugs at the Merchandise Mart.


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 glow sticks at Soldier Field. Discount tickets $30.

Street fair

May 20, 2017

10 miles west

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

Alternative-rock concert

May 20, 2017 (1 p.m.)

31.8 miles south

PIQNIX is an all-star lineup of alternative-rock bands headlined by English synth-pop band “The 1975” at Hollywood Casino Amphitheatre in Tinley Park. Discount tickets $20 to $35.

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. Discount tickets $39.

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.

International festival

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.

Dog walk

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 (3 to 6 p.m.)

9 miles north

Andersonville Wine Walk has two different routes with a dozen retail shops serving wine to adults.

Elmhurst Museum Day

May 21, 2017 (1 to 5 p.m.)

19 miles west

Elmhurst Museum Day includes the museums of art, history, and minerals, plus the plant conservatory, with a free trolley connecting them all. Free.

Doggie dash

May 21, 2017 (morning)

37 miles NW

Dash for the Dogs is a 5K runwalk and a one-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 historic tours 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, plus macaroni & cheese, cornbread, and coleslaw outside 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 five stages, and free carnival rides in Oak Forest.

Magic show

May 26 - July 22, 2017 (9:30 p.m.)

0.7 miles south

The Magic Parlour is an evening of close-up magic by an award-winning magician in the beautiful Palmer House Hilton Hotel. Discount tickets $49.

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 Street (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.

Spectacular bike ride

May 28, 2017 (5:30 to about 9:30 a.m.)

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.

After-work cruise

May 29 - July 31, 2017 (boarding 6 p.m.)

0.7 miles east

An evening cruise aboard the Anita Dee II offers amazing views from the open top deck, dancing, and a pricey bar, departing from 200 N Breakwater Access.

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.

Fireworks cruise

May 31 - July 19, 2017 (Wednesdays, board 7 p.m.)

0.7 miles east

Sunset Booze Cruise with Fireworks features skyline views, DJ music, a cash bar, and fireworks at 9:30 p.m. departing from DuSable Harbor for age 21+. Discount tickets $13.
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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