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Chicken wings festival
May 6, 2018
3 miles SW
Restaurants compete to win the “Best of Fest” award at WingFest, and your ticket includes unlimited samples at UIC Pavilion for age 10+. No pets.
Elmhurst Art in the Park
May 6, 2018
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.
Critics film festival
May 6 – 10, 2018
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.
Hilton Hotels
Lilac festival
May 6, 2018
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.
Chicago attractions
May 6 – June 30, 2018
multiple locations
These discount prices include all taxes and fees.
Aquarium + SkyDeck + Field Museum + more
CityPass gets you into 5 attractions for $107.

Axe throwing (1.5 hours)
Ticket deal $25 (reserve 2 days ahead)

Chicago History Museum
Ticket deal $13

Segway Tour of Downtown Chicago (2 hours)
Ticket deal $37 (reserve 2 days ahead)

The Wizard of Oz
May 8 – 20, 2018
0.4 miles SW
Featuring brightly colored sets, a timeless score, and new special effects, The Wizard of Oz takes you over the rainbow to a magical kingdom full of munchkins, witches, flying monkeys, and wizards at The Chicago Theatre.
Ticket deal $35 to $55

J.C. Superstar
May 8 – 20, 2018
1 mile SW
Jesus Christ Superstar is Andrew Lloyd Webber’s epic rock musical with unforgettable songs, high-energy dance, and powerful storytelling at Lyric Opera House.
Ticket deal $48 to $116

Dinner cruise
May 8 – June 14, 2018
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.
Ticket deal $66 to $82

Tropical musical
May 8 – June 17, 2018
18 miles west
South Pacific is the Rodgers & Hammerstein story of Americans living in exotic lands during World War II, dealing with love, prejudice, and cultural differences at Drury Lane Theatre.
Ticket deal $37 to $45

Roaring Twenties musical
May 9 – 27, 2018
4.8 miles north
It’s 1928, the world is at peace, and the stock market is booming, but issues of life and death face diverse characters we meet as they share their hopes and dreams in the lobby of the Grand Hotel at Theater Wit.
Ticket deal $28

Magic show
May 10 – 27, 2018
3.1 miles NW
The Rosenkranz Mysteries is a “truly unusual and immensely likable magic show” [Chicago Tribune] by a local medical doctor who performs tricks and illusions at Royal George Theatre.
Ticket deal $25 to $38

Urban arts festival
May 11, 2018
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.
Cinco de Mayo
May 11 – 13, 2018
15.4 miles SW
Viva Cinco De Mayo Festival has live music, Mexican food, arts & crafts, a carnival, and family activities outdoors at Toyota Park. Children age 12 and younger are free.
Tour tiny homes
May 11 – 13, 2018 (10 a.m to 8 p.m.)
32.4 miles NW
Tiny homes are getting big attention, and now you can visit 20 of them during Chicago Tiny Home Show at Schaumburg Boomers Stadium, easily reached by Chicago Metra Rail Line. Moms get free admission.
Magic show
May 11 – 25, 2018 (Fridays 7:30 p.m.)
0.5 miles west
Magic & Mystery is an evening of astonishing magic, mind reading, and hypnosis by professional magician Mat LaVore at the Den Theatre.
Ticket deal $20

Magic show
May 11 – 26, 2018
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.
Ticket deal $49

Adult variety show
May 11 – July 21, 2018
7 miles north
Kiss Kiss Cabaret is a fun mix of burlesque, off-color comedy, music, magic, song, and variety acts for age 21+ Fridays and Saturdays at Uptown Underground.
Ticket deal $12 to $14

Science talks
May 12, 2018
1 mile west
Hear six experts talk about fascinating science subjects ranging from animals to engineering at Chicago Science Fest, with exhibits about electric cars, biology, and edible bugs at the Merchandise Mart.
Yoga event
May 12, 2018
1 mile south
Wanderlust 108 combines three events in one: a 5K run/walk, 75 minutes of yoga with DJ music, and 30 minutes of guided meditation, plus other activities at Butler Field in Grant Park. Optional lunch.
Pop music party
May 12, 2018 (2 p.m.)
7 miles north
Watch Europe’s pop singing competition live from Lisbon at Eurovision Song Contest Viewing Party at Dank Haus. Free, with beer and snacks for sale.
Small art fair
May 12, 2018
16 miles NW
Arts & Crafts Adventure is a friendly juried show at Hodges Park in Park Ridge. Repeats in Sept. Free.
Family theater
May 12, 2018 (10 a.m.)
34 miles north
A gullible king buys magical clothes “invisible to fools” and only a young boy can teach him an important lesson about outward appearance in The Emperor’s New Clothes at Marriott Theatre in Lincolnshire.
Ticket deal $9

Pilsen craft fair
May 12 – 13, 2018
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 12 – 20, 2018
13 miles north
Evanston Literary Festival includes dozens of author readings and workshops on its schedule, plus a book fair on May 12 at the library. Free.
Mother’s Day restaurants
May 13, 2018
Chicago locations
OpenTable lists restaurants that offer special brunch, lunch, and dinner menus on Mother’s Day.
Gospel Brunch
May 13, 2018
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 cruise
May 13, 2018
1 mile east
Take a brunch or dinner Chicago Mother’s Day Cruise from Navy Pier.
Mother’s Day Brunch – zoo
May 13, 2018
2.5 miles north
Make a reservation for the Mother’s Day Brunch buffet with live music at the Lincoln Park Zoo. Mom gets a free mimosa.
Mother’s Day run/walk
May 13, 2018
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 13, 2018 (12 to 5 p.m.)
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 13, 2018 (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.
Adult night at the planetarium
May 17, 2018 (6:30 to 10:30 p.m.)
2.5 miles SE
Adler After Dark offers open access, unlimited shows, entertainment, and no-host bars at Adler Planetarium for age 21+. May theme is Planetary Prom: Fire & Ice.
Wine in the garden
May 17, 2018 (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+.
Antiques show
May 17 – 20, 2018
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.
Nerdy comedy
May 17 – 20, 2018
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.
Beer at the conservatory
May 18, 2018 (6 p.m., VIP 5 p.m.)
5 miles west
Enjoy craft beer and food trucks at Beer under Glass indoors and outdoors at Garfield Park Conservatory.
German party
May 18, 2018 (7:30 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.
Small press festival
May 18 – 19, 2018
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.
Wine tasting
May 18 – 20, 2018
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.
Ticket deal $33 to $39 at Goldstar

Ticket deal $33 to $39 at Groupon

May 18 – 20, 2018
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 Maifest listed under May 31.]
French classical music
May 18 & 20, 2018 (7:30 p.m.)
12.7 miles north
Paris in the Springtime stars the Rembrandt Chamber Players performing four works by French composers.
May 18 – St. James Episcopal Cathedral, Chicago
Ticket deal $19

May 20 – Nichols Concert Hall, Evanston
Ticket deal $19

Anime convention
May 18 – 20, 2018
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.
Craft beer week
May 18 – 25, 2018
Chicago locations
Illinois Craft Beer Week [formerly Chicago Craft Beer Week] typically offers hundreds of craft beer events in the greater Chicago area, from special tastings of rare beer to beer dinners. It’s sponsored by the Illinois Craft Brewers Guild.
Dog party
May 19, 2018 (9 a.m. to noon)
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.
Food trucks at the zoo
May 19, 2018 (6:30 to 9:30 p.m.)
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.
Running music festival
May 19, 2018
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.
Ticket deal $30

Baseball pub crawl
May 19, 2018
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.
Ticket deal $10

Asian-American party
May 19, 2018 (7 to 11 p.m.)
6.5 miles SW
Dress up for the Lunar Ball to enjoy music, dancing, restaurant tasting, an open bar, and a silent auction at Zhou B Art Center in Bridgeport.
Street fair
May 19, 2018
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 19, 2018
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.
Charity dinner
May 19, 2018 (6 to 9:30 p.m.)
26.7 miles NW
A $125 ticket to Hunger to Hope gets you a three-course dinner, live music, an international craft market, and a live auction at Renaissance Schaumburg Convention Center.
Riverside Arts Weekend
May 19 – 20, 2018
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 19 – 20, 2018
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.
Civil War event
May 19 – 20, 2018
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 20, 2018 (3 to 6 p.m.)
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 20, 2018 (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 20, 2018
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 20, 2018
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 24, 2018 (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, coleslaw, and watermelon outside the Park Grill.
R & B music festival
May 25, 2018 (7:30 p.m.)
1 mile south
Dress up in black attire for All Black Affair featuring Kindred Family Soul, Jon B, Carl Thomas, Ginuwine, Dru Hill, and a cash bar at Auditorium Theatre.
Ticket deal $73

Tropical beer tasting
May 25, 2018 (6 p.m.)
2.6 miles north
“Sip on tropical-inspired craft beer from more than 60 local and out-of-state breweries and sample gourmet small bites” at Good Libations at Theater on the Lake for age 21+. Creative tropical attire is welcome.
Mexican food festival
May 25 – 27, 2018
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 25 – 27, 2018
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 25 – 27, 2018
144 miles SW
Summer Camp Music Festival typically attracts 20,000 fans watching 125 bands on 9 stages in Chillicothe.
Irish festival
May 25 – 28, 2018
26 miles south
Chicago Gaelic Park Irish Fest offers music, dancing, food, beer, wine, room, vendors, and children’s activities in Oak Forest.
Memorial Day Parade
May 26, 2018
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 26 – 27, 2018 (noon to 10 p.m.)
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.
Art fair in Barrington
May 26 – 27, 2018
38 miles NW
Barrington Art Festival features 130 juried artists, live music, food, and children’s activities. Free.
Games convention
May 26 – 28, 2018
15.3 miles NW
Wolfcon is for players of board games, computer games, and role-playing games at The Pavilion near the airport. Held in May and November.
Movie music
May 27, 2018 (3 p.m.)
0.5 miles south
Chicago Philharmonic plays excerpts from the original scores of Star Wars, Pirates of the Caribbean, Wonder Woman, The Magnificent Seven, etc. during Hollywood Heroes at Harris Theater in Millennium Park.
Ticket deal $20

Spectacular bike ride
May 27, 2018 (opens 5:30 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.
Dirty Dancing
May 30 – June 3, 2018
0.7 miles SW
See the romantic story Dirty Dancing, with passionate dancing and hit songs from the movie live at Cadillac Palace Theatre.
Ticket deal $29 to $59

May 31 – June 3, 2018
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 Mayfest listed under May 18.]
see June

Tim Padavic