Chicago events May 2019. Things to do in Chicago.

Best events for 12 months

Chicago events May 2019

Palestinian film festival

May 1 - 2, 2019
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.

Lilac festival

May 1 - 19, 2019
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.

Famous speakers

May 1 - 21, 2019
Chicago locations
Hear today’s leading authors, thinkers, and fashion icons speak at the Springfest organized by the Chicago Humanities Festival. The theme in 2019 is “Power.”

Bach festival

May 3, 2019
Chicago locations
Bach Week Festival is a series of four classical music concerts in North Chicago and Evanston.

Cinco de Mayo dance

May 3, 2019
4.6 miles NW
Cinco de Mayo Dance Party is a beginner salsa dance class for singles and couples with Mexican refreshments at Duet Dance Studio for age 21+. You can bring your own alcohol.

German wine tasting

May 3 - 4, 2019
(4:30 to 8:30 p.m.)
0.6 miles SW
A ticket to Germany Week Wine Fest includes 10 tastings (each 2 ounces) from among 40 German wines, with chocolate for sale and German exhibitors to browse at Daley Plaza. Lederhosen welcome!

Polish parade

May 4, 2019
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 4, 2019
2 miles south
Chicago Beer Classic has beer from 70 breweries, food vendors, games, and activities on the grass at Soldier Field for age 21+.

Kite festival

May 4, 2019
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.

Progressive party

May 4, 2019
(7 to 11 p.m.)
10.1 miles south
Enjoy dancing, entertainment, an open bar, light bites, DJ music, and performances by Jeezy’s Juke Joint at ChiQ, a fundraiser for the LGBTQ community at South Shore Cultural Center.

Elmhurst Art in the Park

May 4 - 5, 2019
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, with food for sale in Wilder Mansion. Free.

Fountain festival for families

May 5, 2019
(12 to 3 p.m.)
1.1 miles south
Watch as Buckingham Fountain is turned on for the season during Switch on Summer, an event with giveaways, family-friendly activities, and live entertainment. Fee.

Nerdy comedy

May 8 - 11, 2019
5 miles north
If you love comedy about nerdy subjects like Star Trek, Dungeons and Dragons, Buffy the Vampire Slayer, and Jane Austen, then The Chicago Nerd Comedy Festival will keep you laughing at Stage 773.

Urban arts festival

May 10, 2019
1 mile south
Manifest is a full day of student art, live performances, fashion shows, original game design, and literary readings in and around Columbia College. Free.

Beer at the conservatory

May 10, 2019
5 miles west
Enjoy craft beer and food trucks at Beer under Glass indoors and outdoors at Garfield Park Conservatory.

Craft beer week

May 10 - 17, 2019
Chicago locations
Illinois Craft Beer Week typically offers hundreds of craft beer events in the gre ater Chicago area, from special tastings of rare beer to beer dinners. It’s sponsored by the Illinois Craft Brewers Guild.

Food trucks at the zoo

May 11, 2019
2.5 miles north
The Food Truck Social features dozens of trucks selling food and beverages, plus activities, DJ music, and an opportunity to wander Lincoln Park Zoo after hours.

Small art fair

May 11, 2019
16 miles NW
Arts & Crafts Adventure is a friendly juried show at Hodges Park in Park Ridge. Repeats in Sept. Free.

Beer festival

May 11, 2019
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.

Pilsen craft fair

May 11 - 12, 2019
3.5 miles SW
Shop from independent artisans at Renegade Craft Fair, with food trucks and craft cocktails for sale on Halsted Street (from W. 18th Street to S. Canalport Avenue). Free.

Meet the authors

May 11 - 19, 2019
13 miles north
Evanston Literary Festival includes dozens of author readings and workshops on its schedule. Free.

Mother’s Day restaurants

May 12, 2019
Chicago locations
OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Mother’s Day.

Gospel Brunch

May 12, 2019
0.4 miles west
Take Mom to the Gospel Brunch [website has sound] for a fine buffet of Southern and Creole-inspired food and joyful singing at the House of Blues.

Mother’s Day house walk

May 12, 2019
12 miles north
Tour six historic homes plus the Dawes House on the annual Mother’s Day House Walk in North Evanston.

Mother’s Day garden brunch

May 12, 2019
24 miles north
Treat Mom to an elegant Mother’s Day Brunch followed by a walk through the Chicago Botanic Garden in Glencoe.

Small press festival

May 16 - 18, 2019
multiple locations
A zine is a cheap, self-published, underground publication. Chicago Zine Fest offers panel discussions Friday evening, plus exhibitions by 200 writers, artists, and publishers on Saturday. Free.

New art fair

May 17 - 19, 2019
(preview May 16)
4.2 miles SW
Based in London, The Other Art Fair “leads the way in uncovering and nurturing new and innovative creative talent” exhibiting works by 130 emerging artists at Mana Contemporary Chicago.

Art tour by trolley

May 17, 2019
(6 to 8:30 p.m.)
5 miles NW
A ticket for the Trolley Tour includes boxed snacks and a three-hour guided tour by trolley of murals and outdoor art projects. Location varies by month: May is south side, June is north side, and July is west town.

German party

May 17, 2019
(7:30 to 11:30 p.m.)
7 miles north
Celebrate spring and the arrival of Maifest at the Stammtisch - Maifest with traditional white asparagus and Maibock beer in the 6th floor lounge at Dank Haus. Free admission, with food and drinks for sale.

Antiques show

May 17 - 19, 2019
1 mile west
The Chicago Antiques + Art + Design Show promises 100 vendors of fine antiques and decorative & fine arts on floor 7 of the Chicago Merchandise Mart.

Wine tasting

May 17 - 19, 2019
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.


May 17 - 19, 2019
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 1:30 p.m. [Not to be confused with the similar event Maifest on May 30.]

Anime convention

May 17 - 19, 2019
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.

Critics film festival

May 17 - 23, 2019
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.

Science talks

May 18, 2019
1 mile west
Hear six experts talk about fascinating science subjects ranging from animals to engineering at Chicago Science Expo, with exhibits about electric cars, biology, and edible bugs at the Merchandise Mart.

Dog party

May 18, 2019
2.5 miles south
Register online for a 5K walk along the lakefront with your dog at 9 a.m., or arrive at 10 a.m. for the activities, vendors, and entertainment during Bark in the Park on the green near Soldier Field.

Running music festival

May 18, 2019
2.7 miles south
Night Nation Run includes a pre-party with dance music, a 5K run/walk with a starting-line light show, party zones along the course, and an after party stage show with DJs and special effects at Soldier Field.

Baseball pub crawl

May 18, 2019
(12 to 8 p.m.)
5 miles north
Cover Your Bases is a baseball-themed pub crawl that includes 10 bars, beginning at Murphy’s Bleachers. You get a T-shirt printed with “bases” that you cover with stickers from the bars you visit.

Mexican children’s day

May 18, 2019
5 miles SW
Celebrate Mexican culture and family health at Día del Niño Family Festival. Begin at 10 a.m. walking around Harrison Park with children in superhero costumes, followed by games, art, health screenings, and fitness activities at the National Museum of Mexican Art. Free.

Pop music party

May 18, 2019
7 miles north
Watch Europe’s pop singing competition live from Tel Aviv at Eurovision Song Contest Viewing Party at Dank Haus. Free, with beer and snacks for sale.

Street fair

May 18, 2019
(art walk May 17)
10 miles west
What’s Blooming on Harrison offers arts and crafts, artist demos, live music, and dance in Oak Park. Free.

Architectural tour

May 18, 2019
11.8 miles west
Tour innovative homes and buildings designed by famous American architect Frank Lloyd Wright on the Wright Plus Housewalk in Oak Park.

Wine tasting at the zoo

May 18, 2019
(4 to 8 p.m.)
A ticket to Roars & Pours includes seeing the animals at Brookfield Zoo until 6 p.m., and then wine and spirits tasting from 4 to 8 p.m. in the pavilion, with music and food trucks for age 21+.

Riverside Arts Weekend

May 18 - 19, 2019
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 18 - 19, 2019
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.

Hard-core rock festival

May 18 - 19, 2019
15.4 miles SW
Chicago Open Air brings an all-star lineup of 40 rock & heavy metal artists to SeatGeek Stadium.

Civil War event

May 18 - 19, 2019
33 miles west
See a Civil War encampment, meet actors like Abraham Lincoln and Harriet Tubman in costume, hear a brass band, watch a battle at 2:30 p.m., buy food, and shop from vendors during Civil War Days at Naper Settlement.

Wine tasting

May 19, 2019
9 miles north
Andersonville Wine Walk offers you a choice of three different routes that each have 10 retail shops serving wine to adults.

Elmhurst Museum Day

May 19, 2019
(1 to 5 p.m.)
19 miles west
Elmhurst Museum Day includes the museums of art, history, and minerals, with a free trolley connecting all three. Free.

Doggie dash

May 19, 2019
37 miles NW
Dash for the Dogs is a 5K run/walk and a one-mile family walk, followed by awards and food in Barrington, with the proceeds benefiting Animal House Shelter.

Rhubarb Festival

May 19, 2019
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.

Mexican food festival

May 24 - 26, 2019
5.2 miles SW
Mole de Mayo features “mole” and other foods, a crafts market, two stages of entertainment, and a wrestling ring in historic Pilsen (at Ashland & 18th Street). Donation.


May 24 - 26, 2019
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.

Irish festival

May 24 - 26, 2019
26 miles south
Chicago Gaelic Park Irish Fest offers music, dancing, food, beer, wine, room, vendors, and children’s activities in Oak Forest.

Big music festival near Peoria

May 24 - 26, 2019
144 miles SW
Summer Camp Music Festival typically attracts 20,000 fans watching 125 bands on 9 stages in Chillicothe.

Music on the lake

May 24 - Sept. 2, 2019
(Sat. & Sun.)
1 mile east
Hear live music at Live on the Lake in the beer garden at Navy Pier. Free for all ages.

Memorial Day Parade

May 25, 2019
0.5 mile SW
A wreath laying ceremony is 11 a.m. 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 25 - 26, 2019
5 miles north
Celebrate Memorial Day weekend with local bands, entertainers, food, drink, and street vendors at the Belmont-Sheffield Music Festival on N. Sheffield Avenue (from Belmont to Roscoe). Donation.

Block party

May 25 - 26, 2019
(12 to 10 p.m.)
6.7 miles north
Mayfestiversary offers a full lineup of music, plenty of food trucks, a kids’ corner, and local beer on Ravenswood Avenue (from West Belle Plaine to West Cuyler Avenue). Donation.

Art fair in Barrington

May 25 - 26, 2019
38 miles NW
Barrington Art Festival features 130 juried artists, live music, food, and children’s activities. Free.

St. Charles art show

May 25 - 26, 2019
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.

Cirque + symphony

May 26, 2019
(7:30 p.m.)
0.5 miles south
Watch aerial flyers, acrobats, contortionists, dancers, jugglers, and strongmen move to music when Chicago Philharmonic & Cirque de la Symphonie perform together at Harris Theater in Millennium Park.

Spectacular bike ride

May 26, 2019
1 mile south
Register to ride your bike on 15-mile Lake Shore Drive when it closes to vehicles during Bike the Drive, and then join the after-festival until noon at Butler Field.


May 30 - June 2, 2019
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. [Not to be confused with the similar event Mayfest on May 17.]

Whiskey tasting

May 31, 2019
1.9 miles west
Taste 60 whiskeys and hear the band St. Paul & The Broken Bones at WhiskyX Chicago, with food trucks and restaurant food for sale at Revel Fulton Market for age 21+.

Gospel music festival

May 31 - June 1, 2019
0.5 miles south
Hear gospel choirs and soloists at the Chicago Gospel Music Festival at the Chicago Cultural Center and Millennium Park. Free.

Greek festival

May 31 - June 2, 2019
5 miles north
Lincoln Park Greek Fest serves Greek food, music, dancing, and a craft fair on Sheffield Avenue outside St. George Greek Orthodox Church. Free.

Taste of Mexico

May 31 - June 2, 2019
9 miles SW
Taste of Mexico offers food from 20 restaurants, music, and carnival rides at 26th & California Avenue. Free.

Stamp show

May 31 - June 2, 2019
17.6 miles NW
See postage stamp exhibits and shop from 25 dealers at Compex in River Grove. Free.

Small-town festival

May 31 - June 2, 2019
70 miles NW
Harvard Milk Days has dozens of events, including a parade (Saturday 1 p.m.), milk-drinking contest, talent show, carnival, petting zoo, entertainment, races, and fireworks (daily 10 p.m.). See schedule. Free.

Innovative theater

May 31 - June 9, 2019
5 miles north
Physical Theater Festival includes four creative theater shows that tell stories physically and visually, workshops, and a Monday-night showcase of short theater at Stage 773.

Arts festival

May 31 - June 9, 2019
8 miles north
Pivot Arts Festival features dozens of innovative performances, including world premieres, in Edgewater and Uptown.

Ravinia music festival

May 31 - Sept. 15, 2019
23 miles north
See nationally known performers at Ravinia Festival, billed as America’s oldest outdoor music festival at Ravinia Park in Highland Park.

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