Chicago events calendar for May 2014. Best festivals, fun things to do, weekend street fairs, kids activities, and free entertainment in Chicago, Illinois.

events for 12 months
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May 2014

Enjoy the best Chicago events, festivals, and things to do in May 2014 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.

Palestine Film Festival

May 1, 2014 (begins April 19)

0.5 mile SW

The Palestine Film Festival exhibits and promotes films by Palestinian directors as well as films about Palestine at the Gene Siskel Film Center. Cost.

Movies and music festival

May 1 - 4, 2014

5 miles NW

The Chicago International Movies & Music Festival (CIMMfest) is “where movies and music meet.” See films with a music connection by day, and hear live music with a film connection by night at Wicker Park and Logan Square. Cost.

Art festival in homes

May 1 - 25, 2014

Chicago locations

Chicago Home Theater Festival transforms 20 homes into neighborhood sites for art, performances, and films. Pre-party April 30; closing-night event. Cost.

Fashion show

May 2, 2014

0.5 mile south

Fashion 2014 presents designs by 300 students at the School of the Art Institute of Chicago at Millennium Park’s Chase Promenade. Cost.

Wine tasting

May 2 - 3, 2014

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. Cost.

Vintage fashion sale

May 2 - 4, 2014

2 miles west

Shop for vintage clothing, jewelry, and fashion from 75 vendors at Modern Vintage Chicago in Randolph Street Market. May 2 evening only. Repeats Oct. Cost.

Cinco de Mayo

May 2 - 4, 2014

10 miles SW

Cinco de Mayo Festival features live music, authentic foods, arts and crafts, and activities for families on W 26th St. at Kostner. Free.

Bach festival

May 2 - 4, 2014 (begins April 25)

Chicago locations

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

Polish parade

May 3, 2014

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. Begins 11:30 at Buckingham Fountain. Goes up Columbus. Free.

Children’s kite festival

May 3, 2014

6 miles north

Kids 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. Free.

Hobbies on display

May 3, 2014

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 3, 2014

Chicago location undecided

Flagship and rare beers will pour as well as one-of-a-kind concoctions at Mash Tun Festival. Cost.

Zombie Run

May 3, 2014

45 miles north

Dodge zombies who try to pop your balloons (or be a zombie) at the Zombie Run 5K in Grayslake.

Japanese flower arranging

May 3 - 4, 2014

5 miles west

A Weekend in the Path of Flowers is an exhibition of ikebana flower arranging taught by the Ikenobo School, with demonstrations twice daily at Garfield Park Conservatory. Free.

Elmhurst Art in the Park

May 3 - 4, 2014

17 miles west

Elmhurst Art in the Park is a juried show of fine art, craft, and design, held rain or shine at Wilder Park in Elmhurst. Free.

Lilac festival

May 3 - 18, 2014

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. Schedule.

Touch a Truck

May 4, 2014

21 miles north

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

Stages, Sights & Sounds

May 6 - 24, 2014

Chicago locations

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

Blues dance

May 8 - 11, 2014

multiple locations

BluesShout includes weekend workshops and dances with live music that go late into the night. Cost.

Wine tasting

May 9, 2014

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. Cost.
Chicago, Illinois
May 2014

American Beer Classic

May 10, 2014

2 miles south

American Beer Classic has hundreds of beers, beer seminars, live music, and field tours at Soldier Field.

Zombie Pub Crawl

May 10, 2014 (2 p.m.)

8 miles north

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

Small art fair

May 10, 2014

16 miles NW

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

Mother’s Day Brunch - Art Institute

May 11, 2014

1 mile south

Enjoy a brunch buffet at Terzo Piano or a relaxed a la carte brunch at the Museum Cafe in the Art Institute of Chicago. Reservations advised.

Mother’s Day music

May 11, 2014

7 miles north

Enjoy coffee, cake, and classical piano at Kaffee, Kuchen & Klavier at Dank Haus German Center.

Mother’s Day Brunch - Brookfield Zoo

May 11, 2014

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 Brunch - Botanic Garden

May 11, 2014

24 miles north

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

Beer at the conservatory

May 15, 2014

5 miles west

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

Craft beer week

May 15 - 25, 2014

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 Institute party

May 16, 2014

1 mile south

Young people can mix and mingle, visit the bar, and rock out to music at After Dark in the Modern Wing of the Art Institute of Chicago. Cost.

Urban arts festival

May 16, 2014

1 mile south

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

Art fair indoors & outdoors

May 16 - 17, 2014

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 16 - 18, 2014

5 miles NW

Mayfest [website has sound] is bands in a giant tent, festival food, pretzels, and beer. Saturday is kids’ day. Sunday is a pet pageant & expo. At 3100 N Ashland Ave. Cost. (Don’t confuse with Maifest on May 29.)

Anime convention

May 16 - 18, 2014

16 mile NW

Anime Central (ACen) is the largest Midwest anime, manga and Japanese popular culture convention, at the Hyatt Regency O’Hare. Cost.

Architectural tour

May 17, 2014

Greater Chicago area

Tour innovative homes and buildings designed by Frank Lloyd Wright on the All Wright Housewalk. Cost.

Riverside Arts Weekend

May 17 - 18, 2014

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 17 - 18, 2014

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 17 - 18, 2014

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 18, 2014 (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 18, 2014

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.

Wine at Botanic Garden

May 22, 2014 (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. Cost.


May 23 - 25, 2014

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 barbecue in Westmont. Free.

Irish festival

May 23 - 26, 2014

26 miles south

Chicago Gaelic Park Irish Fest offers music, theater, storytelling, dancing, and family entertainment on six stages in Oak Forest. Cost.

Wisconsin chocolate festival

May 23 - 26, 2014

80 miles north

ChocolateFest includes a carnival, family activities, food vendors, chocolate decorating & eating contests, music, and a beer garden in Burlington, WI. Cost.

Memorial Day Parade

May 24, 2014

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 24 - 25, 2014

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.

Bicycle along the lake

May 25, 2014

1 mile south

Ride your bike up to 15 miles each way on Lake Shore Drive when it shuts down for five hours during Bike the Drive. Enter at S Columbus Dr. and Jackson downtown. Register early. Cost.


May 29 - June 1, 2014

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 16.)

Millennium Art Festival

May 30 - June 1, 2014

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 30 - June 1, 2014

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.

Taco festival

May 30 - June 1, 2014

8 miles SW

Festival del Taco includes tacos by local restaurants, music, and crafts at Kostner and 26th St. Donation.

Vegetarian parade

May 31, 2014

1.3 miles south

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

Mexican children’s day

May 31, 2014

2.8 miles SW

Celebrate Mexican culture and family health at Día del Niño Family Festival. Begin with a two-mile walk from the National Museum of Mexican Art to UIC Forum. Continue with games, art, and activities. Free.

Urban scavenger hunt

May 31, 2014

0.7 miles east

Your team of 2 to 4 people will solve clues, tackle challenges, and race for cash prizes in the Great Urban Race beginning at Lizzie McNeill’s.

Pet parade

May 31, 2014 (9:30 to 11 a.m.)

17 miles SW

The LaGrange Pet Parade includes marching bands, floats, clowns, and a creative costume contest. It begins at Cossitt Ave. and LaGrange Rd. Free.

Run with dogs

May 31, 2014

37 miles NW

Dash for the Dogs is a 5K followed by awards and food to benefit Animal House Shelter in Barrington.

Deerfield art festival

May 31 - June 1, 2014

27 miles north

Deerfield Festival of Fine Arts has arts & crafts, food, music, kids’ area at Deerfield Rd. & Park Ave. Free.
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events for 12 months

May 2014 calendar of events in Chicago. What to do in Chicagoland today, this weekend, this month. Special events, festivals, things to do in Chicago, IL.