Chicago events calendar for May 2015. 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 2015

Enjoy the best Chicago events, festivals, and things to do in May 2015 with this calendar of events.

Events are listed by starting date, and all dates are confirmed. Mileage is from the Wrigley Building in downtown Chicago, Illinois.

NFL football festival

May 1 - 2, 2015 (begins April 30)

1 mile south

NFL Draft Town [sound] is a free fan festival in Grant Park with games, exhibits, kids’ play, autographs, and food vendors, plus live music Sat. at 8 p.m.

Bach festival

May 1 & 3, 2015

Chicago locations

Bach week festival is a series of four classical music concerts in North Chicago and Evanston.

Joffrey Ballet

May 1 - 3, 2015 (also April)

0.7 miles SW

Joffrey Ballet performs four gorgeous New Works at the Cadillac Palace Theatre.

Discount tickets.

Musical theater

May 1 - 3, 2015 (also April)

1 mile SW

Carousel features the beautiful songs of Rodgers and Hammerstein at Civic Opera House.

Discount tickets.

Interracial drama

May 1 - 3, 2015 (also April)

4.7 miles north

An Issue of Blood is the story of a cursed wealthy woman, crimes of passion, and a love triangle in early America at Victory Gardens.

Discount tickets.

Hit musical comedy

May 1 - 3, 2015 (begins April 30)

12 miles west

The 25th Annual Putnam County Spelling Bee is a musical about overachievers, described as irresistible and riotously funny by the New York Times, in Oak Park. Discount tickets.

Music festival in Edison Park

May 1 - 3, 2015

13 miles NW

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

Film festival

May 1 - 7, 2015

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.

Comedy about identical twins

May 1 - 9, 2015 (also April)

12 miles north

The Venetian Twins is a classic play about courtship and mistaken identity, full of frenzied, slapstick farce at Piccolo Theatre in Evanston.

Discount tickets.

Cool cabaret

May 1 - 16, 2015

3.3 miles SW

The Devil’s Cabaret includes aerialists, a rock band, a hosted craft beer bar, and “seven sinful acts” for age 21+ in a warehouse at Redmoon Theater.

Discount tickets.

A play about aging parents

May 1 - 16, 2015 (also April)

10 miles north

The Bird Feeder Doesn’t Know debates when kids must care for their parents and when they can finally leave the nest, at Raven Theatre.

Discount tickets.

The Book of Mormon

May 1 - 17, 2015 (also April)

0.8 miles south

The Book of Mormon, winner of 9 Tony Awards, is a musical at Bank of America Theatre.

Discount tickets.

Comedy about dating

May 1 - 17, 2015 (also April)

3 miles north

First Date is a funny romantic musical celebrating the search for love with humor and optimism, live at the intimate Royal George Theatre.

Discount tickets.

Comedy of woman vs. Mafia

May 1 - 24, 2015 (also April)

4.8 miles north

All’s Well That Ends Well is a comedic battle of the sexes that places Shakespeare’s characters in the 1950s Mafia world at Theater Wit.

Discount tickets.

Game of Thrones parody

May 1 - 29, 2015 (Fridays from April)

5 miles north

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

Discount tickets.

Tribute to the ‘80s

May 1 - 30, 2015 (also April)

4.5 miles north

Revisit the songs, movies, TV, and pop-culture of 1980s America in The Power of Prom, a new musical comedy at Annoyance Theatre.

Discount tickets.

Classic Russian play

May 1 - June 6, 2015 (also April)

3.4 miles NW

Three Sisters who once led a privileged life must cope with misfortune and life in a tiny Russian town in Chekhov’s play at The Den Theatre.

Mother daughter drama

May 1 - June 7, 2015 (also April)

3 miles north

Bittersweet memories recall a mother and daughter relationship in The Divine Order of Becoming at Greenhouse Theater Center.

Discount tickets.

Award-winning musical

May 1 - June 7, 2015 (also April)

19 miles west

Billy Elliot features inspiring songs by Elton John and high-energy dance that earned it the title “Broadway musical of the decade” from Time Magazine at Drury Lane Theatre in Oak Brook.

Discount tickets.

Science-fiction Shakespeare

May 1 - June 14, 2015 (also April)

7 miles north

The characters of Macbeth fight with light sabers and travel in outerspace in MacSith at Pendulum Space.

Discount tickets.

Johnny Cash show

May 1 - June 28, 2015 (begins April 30)

7.5 miles north

Ring of Fire features the story & music of legendary Johnny Cash at Mercury Theater.

Discount tickets.

Rock legends concert

May 1 - Sept. 27, 2015 (also April)

3.8 miles north

Million Dollar Quartet recreates the night Elvis, Jerry Lee Lewis, Johnny Cash, and Carl Perkins played together at Sun Records and includes 21 rock hits sung live at Apollo Theater. Discount tickets.

Cinco de Mayo - bar crawl

May 2, 2015 (arrive by 11:30 a.m.)

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.

Polish parade

May 2, 2015 (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 Dearborn Street from Lake to Van Buren. Free.

Kids’ kite festival

May 2, 2015

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 2, 2015 (2 p.m.)

8 miles north

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

Hobbies on display

May 2, 2015

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 and wine festival

May 2, 2015

28 miles SW

Tinley Park Brew & Vine Festival features breweries, vintners, restaurants, and live entertainment at Tinley Park Convention Center.

Meet celebrities

May 2 - 3, 2015 (preview May 1)

16 miles NW

Where can you meet former stars from Adam West to Henry Winkler? Attend The Hollywood Show in Hilton Rosemont near Chicago O’Hare.

Discount tickets.

Elmhurst Art in the Park

May 2 - 3, 2015

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 2 - 3, 2015

17 miles NW

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

Discount tickets.

Gluten-free expo

May 2 - 3, 2015

28 miles NW

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

Family theater

May 2 - 17, 2015 (also April)

10 miles north

A gorilla and a scrappy dog set out to save a baby elephant in The One and Only Ivan, based on a children’s book, at Lifeline Theatre.

Discount tickets.

Lilac festival

May 2 - 17, 2015

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.
May 2015

Campy burlesque

May 2 - July 25, 2015 (Saturdays)

4.5 miles north

Burlesque is More gets high marks for its entertaining and funny combination of striptease & improvisation at Annoyance Theatre and Bar.

Discount tickets.

Batman burlesque

May 2 - July 25, 2015 (midnight)

5 miles NW

Holy Bouncing Boobies! A Batman Burlesque is a campy, sexy, silly show of heroes versus villains at Gorilla Tango Theatre.

Discount tickets.

Touch a Truck

May 3, 2015

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.


May 5 - 21, 2015

5 miles south

Watch the White Sox play at U.S. Cellular Field.

Art festival in homes

May 5 - 24, 2015

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.

Magic show

May 6 - Aug. 26, 2015 (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.

Sexy ballet

May 7 - 9, 2015

0.5 miles south

See a ballet version of the steamy Pulitzer Prize winning drama A Streetcar Named Desire at Harris Theater in Millennium Park.

Discount tickets.

Sound of Music

May 7 - 17, 2015

16 miles NW

See the beloved musical Sound of Music about a singing family, live in Skokie.

Discount tickets.

Stages, Sights & Sounds

May 7 - 20, 2015

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 8, 2015 (3 shows)

0.5 mile south

Fashion 2015 presents designs by students of the School of the Art Institute of Chicago at Millennium Park’s Chase Promenade.

Small press festival

May 8 - 9, 2015

2.5 miles west

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

American Beer Classic

May 9, 2015

2 miles south

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

Baseball pub crawl

May 9, 2015 (12 to 9 p.m.)

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.

Promo code “secondbase” saves $6.

Family train show

May 9, 2015 (1 and 4 p.m.)

16 miles NW

Kids who watch the animated TV show Chuggington will love stage show Chuggington Live! The Great Rescue Adventure at Rosemont Theatre.

Small art fair

May 9, 2015

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 10, 2015

Chicago locations

OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Mother’s Day.

Mother’s Day run/walk

May 10, 2015 (8 a.m.)

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 brunch & art

May 10, 2015

1 mile south

Make a reservation for Mother’s Day Brunch at Terzo Piano in the Art Institute of Chicago and then see art.

Mother’s Day cruise

May 10, 2015

1 mile east

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

Mamma Mia on Mother’s Day

May 10, 2015 (noon)

6 miles north

Enjoy a 1970s fashion show and contest, and then see the movie Mamma Mia, which features hit songs by Abba at Music Box Theatre.

Discount tickets.

Mozart on Mother’s Day

May 10, 2015 (7 p.m.)

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.

Mother’s Day zoo brunch

May 10, 2015 (11 a.m. or 1:30 p.m.)

14 miles SW

Enjoy a champagne Mother’s Day Brunch at the Brookfield Zoo.

Mother’s Day garden brunch

May 10, 2015 (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.

Meet the authors

May 11 - 18, 2015

13 miles north

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

Award-winning “Jersey Boys”

May 12 - 24, 2015

0.7 miles SW

Broadway hit musical Jersey Boys is a rags-to-riches story of twenty-somethings Frankie Valli and The Four Seasons at Cadillac Palace Theatre.

Discount tickets.

Underground film festival

May 13 - 17, 2015

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.

Beer at the conservatory

May 14, 2015

5 miles west

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

Craft beer week

May 14 - 24, 2015

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 15, 2015 (5:30 p.m.)

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.

Museum party

May 15, 2015 (9 p.m.)

1 mile south

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

Urban arts festival

May 15, 2015

1 mile south

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

Wine tasting

May 15 - 16, 2015

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.

Art fair indoors & outdoors

May 15 - 16, 2015

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 15 - 17, 2015

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 May 28.)

Anime convention

May 15 - 17, 2015

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 16, 2015

Greater Chicago area

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

Riverside Arts Weekend

May 16 - 17, 2015

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 16 - 17, 2015

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 16 - 17, 2015

19 miles west

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

Japanese children’s festival

May 16 - 17, 2015

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.

Elmhurst Museum Day

May 17, 2015 (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.

Doggie dash

May 17, 2015

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 17, 2015

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.

California wine tasting

May 20, 2015 (6 to 9 p.m.)

2 miles west

Try wine from California West Sonoma Coast vintners at West of West Wine Festival at City Winery.

Seductive drama

May 21 - June 21, 2015

9 miles north

Les Liaisons Dangereuses is a play about seduction and revenge that led to Oscar-winning film Dangerous Liaisons, at Raven Theatre.

Discount tickets.


May 22 - 24, 2015

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 22 - 25, 2015

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 23, 2015

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.

Pop music party

May 23, 2015 (2 p.m.)

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.

Belmont-Sheffield music fest

May 23 - 24, 2015

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.

St. Charles art show

May 23 - 24, 2015

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 24, 2015 (5:30 to 9:30 a.m.)

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.

Hawaiian pub crawl

May 24, 2015 (12:30 p.m.)

17 miles NW

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

Discount tickets.

Wine at Botanic Garden

May 28, 2015 (6 to 8 p.m.)

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 28 - 31, 2015

8 miles NW

The German festival known as Maifest Chicago serves beer, brats, sauerkraut, and music in Lincoln Square at Lincoln Ave. and Leland Ave. Free. (Don’t confuse with Mayfest on May 15.)

Gospel music festival

May 29 - 31, 2015

0.5 miles south

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

Millennium Art Festival

May 29 - 31, 2015

0.5 mile south

The Millennium Art Festival features artwork, food from local restaurants, and live easy-listening music on Lake Street at Michigan Avenue. Free.

Division Street festival

May 29 - 31, 2015

4 miles NW

Do Division Street Fest & Sidewalk Sale has rousing live music, a sidewalk sale, a fashion show, and a family fun fest (Sat. & Sun.) on Division Street between Damen and Leavitt. Donation.

Vegetarian parade

May 30, 2015 (noon)

1.3 miles south

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

Wine festival

May 30, 2015 (1 to 9 p.m.)

11 miles west

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

Pet parade

May 30, 2015 (begins 9:30 a.m.)

17 miles SW

The LaGrange Pet Parade includes marching bands, floats, clowns, and a creative costume contest. Line up is 8:30 a.m. at Cossitt Ave. & LaGrange Rd. Free.

Wine tasting

May 30 - 31, 2015

4 miles north

Taste a dozen wines at Lincoln Park Wine Festival, which has tented wine and food pavilions, live music, and crafts at Jonquil Playlot Park. Discount tickets.

Deerfield art festival

May 30 - 31, 2015

27 miles north

Deerfield Festival of Fine Arts has arts & crafts, food, music, kids’ area at Deerfield Rd. & Park Ave. Free.

Chamber music

May 31, 2015 (3 p.m.)

12 miles north

Rembrandt Chamber Players perform three pieces, including Tchaikovsky's emotionally stormy Souvenir of Florence, at Nichols Concert Hall in Evanston.

Discount tickets.

Next month:June 2015
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May 2015 calendar of events in Chicago, IL. Best events, fairs, festivals, and things to do in Chicago, Illinois.