Everything You Need to Do in Chicago This Spring

As precautionary measures to combat the spread of COVID-19, or coronavirus, continue, please note that many events are subject to cancellation. Please check back frequently as we'll be updating stories as changes occur.

Spring cleaning. Planting flowers. Clothes shopping. These are things you should do in spring. Drinking beer on the field at Soldier Field. Trading work for baseball. Eating chicken wings outside of a church. These are things you need to do in Chicago in spring. Congratulations on surviving another Chicago winter. You’ve earned it, kid.

Get a sweet new Malort tattoo at the Chicago Tattoo Arts Convention

Friday, March 20 - Sunday, March 22
Donald E. Stephens Convention Center
Some of the country’s top tattoo artists and vendors set up shop in Chicago for this annual inkfest featuring tattoo contests, seminars, live entertainment such as fire-eating, and “aerial burlesque,” plus appearances by television tattoo personalities.
Cost: $22 per day or $45 for 3-day pass

Drink, drink, and be merry at WhiskyFest Chicago

Friday, March 27
Hyatt Regency
300+ of the finest whiskies from around the world. Free seminars conducted by whiskey experts. Gourmet food buffet. You?
Cost: $275

Blow off work to catch the Cubs (and/or the Sox) on Opening Day

Monday, March 30
Wrigley Field
So what if the Cubs home opener versus Pittsburg falls on a Monday this year? Again? You’re taking the day off. Again. It might as well be an official municipal holiday. (For those seeking an extra day off, the White Sox home opener takes place Thursday, March 26 vs. Kansas City.)
Cost: $59-$267

Rock to ‘80s jams as you hunt for Easter eggs at Bunny Rock

Saturday, April 11
Montrose Harbor
For something different this Easter weekend instead of another boring brunch, race around Montrose Harbor gathering eggs while ‘80s music soundtracks your scavenging. Maybe hit a boring brunch after.
Cost: $40

Chicago Cocktail Social
Chicago Cocktail Social | Green Curtain Events‎

Drink allll the drinks at Chicago Cocktail Social

Thursday, April 16
Galleria Marchetti
Sip drinks from some of Chicago’s top cocktail slingers including Violet Hour, Berkshire Room, Scofflaw, and Heavy Feather paired with live music and food from Root’s Pizza, Chicago’s Dog House, West Town Bakery, STK, and more.
Cost: $45-$65

Become a Chicago food expert at Baconfest Chicago & Da Best Fest

Friday, April 17 - Saturday, April 18
UIC Dorin Forum
Sample inventive bacon dishes from dozens of top local chefs and restos over the course of three pork-and-booze-packed weekend sessions at Baconfest, with prizes awarded for best bacon dishes as well as achievement in the esteemed field of “bacon arts.” Also new this year is Da Best Fest on Friday, featuring iconic Chicago eats and hosted by Doug Sohn of Hot Doug’s fame.
Cost: $60-$160 per session for Baconfest; $75-$130 for Da Best Fest; $140-$240 for both fests bundle

Meet your favorite porn stars and learn to twerk at Exottica Expo

Friday, April 17 - Sunday, April 19
Donald E. Stephens Convention Center
There’s appearances by famous porn stars. There’s sex seminars and Q&As. There’s a twerking contest and pole dancing championship. 
Cost: $40-$46 for 1-day pass; $80-$330 for 3-day pass

Expand your culinary (and cultural) horizons at I Heart Halal

Friday, April 17 - Sunday, April 19
Navy Pier
Halal products in every category -- from food and fashion to sports and travel -- will be featured at this event along with culinary demonstrations, educational sessions, fashion shows, and more.
Cost: $20-$30

Celebrate the high holiday of 4/20 at Waldos Forever Fest

Saturday, April 18
Outside Dispensary 33
Happy 4/20, Chicago! Celebrate the high holiday (pun intended) during the first year of legal green in Illinois with this cannabis-themed party from the folks at Do312 featuring music, education, and fun for cannabis lovers.
Cost: Free

Shop local (and rock local) during Record Store Day

Saturday, April 18
Various locations
Visit your local independent record store (here’s a good place to start) for special deals and events at participating stores.
Cost: No cover


Wing it at Chicago WingFest

Saturday, April 18
Credit Union 1 Arena at UIC
This annual event features chicken wings from top local restos in four categories (hot, mild, BBQ, and exotic) plus live music, wing eating competitions, and juried awards for “Best of the Fest.”
Cost: $50-$100

House beers on the Bears home field at the Chicago Beer Classic

Saturday, May 2
Soldier Field
Unless you’re hiding a pass rush on par with Khalil Mack, this is probably your only chance to get on the Soldier Field grass. Even better when there’s 150+ craft beers involved and (hopefully) no tackling. The two-session event includes stadium food and VIP tours, games and activities, and brewer meet-and-greets.
Cost: $49-$69 per session

Do something nice for your ears at the CHIRP Record Fair & Other Delights

Saturday, May 2
Plumbers Hall
Dig through thousands of crates of vinyl with the help of live music, beer/wine/coffee, food from Big Star and First Slice, CDs/DVDs and posters and a gear swap at this annual fundraiser for local independent station CHIRP Radio.
Cost: $8-$25

Get dolled up for the Derby at the I|O Godfrey Kentucky Derby Viewing Event

Saturday, May 2
I|O Godfrey
Hit up one of Chicago’s most stunning rooftop bars for this festive Kentucky Derby-themed event featuring bourbon classes, a special Derby Day menu, and prizes for best dressed.
Cost: $30 and up

Crawl to bars in a ridiculous sombrero during Bar Crawl de Mayo

Saturday, May 2
Various River North bars
This bar crawl includes a brunch buffet and drink specials at River North bars like Hubbard Inn, Moe’s Cantina, and Point & Feather. Yes, it’s Cinco de Mayo. What else are you gonna do?
Cost: $10

 Food Truck Social
Food Truck Social | Lincoln Park Zoo

Strap on a feed bag and roll into the zoo at the Food Truck Social

Saturday, May 9
Lincoln Park Zoo
A fine assemblage of four-wheeled eats including grilled cheese, tacos, pierogies, donuts, and other edible offerings from local food trucks roll into the zoo after hours for this food fest with live music, booze, and activities.
Cost: $10

Bask in the height of beer nerd nirvana during Illinois Craft Beer Week

Friday, May 15 - Friday, May 22
Various locations
It’s Lollapalooza for beer nerds as Illinois Craft Beer Week (formerly known as Chicago Craft Beer Week) sets up shop across the city with a monster array of specialty brewskis and events, kickstarted by the annual “Beer Under Glass” event at Garfield Park Conservatory.
Cost: TBA

Light up the world’s first running music festival at Night Nation Run

Saturday, May 16
Soldier Field
If running at night wearing a glow necklace around a music-filled course with live DJs, light shows, bubble zones, and neon and black lights sounds like a good idea to you, welcome to your happy place.
Cost: $30-$60

Put down the Franzia and join the Chicago Wine Fest

Saturday, May 16
Lincoln Park Zoo
Visit the zoo with wine glass in hand to take in the spring vibes alongside food and live performances, plus VIP access for an early crack at the stash. Three sessions from noon to 10 pm.
Cost: $35-$60 per session

Catch some high-flying antics at Mole de Mayo

Friday, May 22-Sunday, May 24
18th & Ashland
This massive Latin-flavored Memorial Day rager features lucha libre wrestling, art, music, and, of course, top local chefs and restaurants offering their finest interpretation of authentic Mexican mole dishes.
Cost: $5-$10 suggested donation

 Bike the Drive
Bike the Drive | Active Transportation Alliance

Envision a car-free world (then eat pancakes) during Bike the Drive

Sunday, May 24
Lake Shore Drive
Celebrate summer’s unofficial kickoff by biking all 30 round-trip miles of Lake Shore Drive (or as far as you feel like it) while the road is closed to vehicular traffic in the morning, followed by a post-ride festival with live music, breakfast, and beer in Grant Park.
Cost: $45-$68

Make whiskey your new haircut beverage of choice at The WhiskyX Chicago

Friday, May 29
Revel Fulton Market
What fest has 60+ whiskeys, local food trucks, free haircuts, and an appearance by Justin Willman of Netflix’s Magic for Humans? This fest.
Cost: $50-$300

Do sangria drinks and weird dance moves at Do Division Street Fest

Friday, May 29-Sunday, May 31
Division Street between Damen and Leavitt
One of Chicago festival season’s earliest street fests is also one of its best, with two live music stages plus food/drink, a runway show, DJs, local vendors, and more. Prepare for a serious intake of sangria.
Cost: $10 suggested donation

Rock the world’s largest free blues festival at Chicago Blues Fest

Friday, June 5-Sunday, June 7
Millennium Park
It’s Blues Fest. Do you really need a description? This year’s acts include Shemekia Copeland, John Primer, and Cedric Burnside.
Cost: Free

Worship at the church of the chicken wing gods at Wingout Chicago

Saturday, June 6-Sunday, June 7
St. Michael’s Church parking lot
Five words: Outdoor chicken wing block party. 20+ varieties of wings from jerk to umami from top local restos will be on hand, alongside live music and plenty of “adult beverages” outside of St. Michael’s Church.
Cost: $36-$75

57th Street Art Fair
57th Street Art Fair

Get a taste (and drink) of Hyde Park at the 57th Street Art Fair

Saturday, June 6-Sunday, June 7
57th between Kenwood and Woodlawn
The Old Faithful of South Side art festivals takes over Hyde Park as spring turns to summer with some of the finest art you’ll see all year plus live music and a food court. While you’re here, check out the Hyde Park Brew Fest held the same weekend.
Cost: Free

Douse your spring in BBQ sauce at Ribfest Chicago

Friday, June 12-Sunday, June 14
Lincoln/Damen/Irving Park
This Northcenter tradition unfurls 27 tons of pork and 25 hours of live music from local indie bands, plus voting for best ribs. Pro tip: Pack napkins.
Cost: $10 suggested donation

Choose your own adventure at the Old Town Art Fair

Saturday, June 13-Sunday, June 14
Various locations
This summer staple features 250+ artists, a neighborhood garden walk, live music, and food/drink in the Old Town Triangle District. There’s also the Wells Street Art Festival on North & Wells the same weekend, in case you can’t get enough.
Cost: $10 suggested donation

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Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile