Everything You Need to Do in Chicago This Winter

Updated On 02/15/2018 at 10:42AM EST Updated On 02/15/2018 at 10:42AM EST
Voyager New Year's Party | Kohl Murdock
donut fest
donut fest | Kailley Lindman/Thrillist
Saturday - Saturday
Jan 13-Feb 3
The Rookery
Upstairs at The Rookery turns into Room 237 -- a pop-up inspired by The Shining -- this winter with a weekly showcase of original music in a dark playpen of bourbon drinks and mysterious energy that Stanley Kubrick would feel right at home in. There will be bourbon on the rocks and live music waiting.
Cost: No cover
Friday - Thursday
Jan 26-Feb 8
Various locations
Hundreds -- yes, hundreds -- of Chicago restaurants are offering exciting deals to try during our city's very own winter Restaurant Week, so it's time to get out there and feed your bodies. We've rounded up the most exciting deals for your perusal.
Cost: $22, $33, or $44, depending on the meal
Jan 28
Chop Shop
It’s a damn donut fest. You don’t need any more convincing than that.
Cost: $35-$50 per session
Pancakes & Booze Art Show
Pancakes & Booze Art Show | Pancakes & Booze Art Show
Feb 3
This annual boil of authentic Door County whitefish served from a massive flaming cauldron paired with live music and bratwurst is your perfect antidote for the mid-winter blues. This is the fourth year FitzGerald's has hosted its fish boil.
Cost: Admission is $15, plus $12-$17 depending on your choice of dinner
Feb 4
Hit venerable South Loop punk venue Reggie’s for a Super Bowl Bash featuring eating contest, chili cook-off, and live music before the game. Or watch the game somewhere else… you’ve got plenty of options.
Cost: $15 all-you-can-eat buffet
Friday - Sunday
Feb 9-25
Emporium (all locations)
Ignite the Olympic torch at Emporium’s Wicker Park, Logan Square, and Fulton Market locations with events like pinball and air hockey tourneys, NBA Jam and Mario Cart face-offs, and, of course, a closing ceremony where prizes will be awarded.
Cost: No fee to join the games
Feb 10
John Barleycorn
Join underwear-clad racers who will make a short pre-Valentine’s Day run in their skivvies in the neighborhood around John Barleycorn, with the party continuing in the bar after.
Cost: $40
Feb 10
Ravenswood Events Center
This Chicago pizza fest showcases pizza from 20 of the city’s finest pizza makers including Lou Malnati’s, Roots, Salerno’s, and Pie Eyed, plus a rooftop dessert lounge, beer tastings, live music, and games.
Cost: $25 per session
Feb 10
Every year the Metro throws a winter block party, and every year it's a blast. This year’s event is inspired by the Spike Lee film Do the Right Thing, showcasing the power of hip-hip to bring communities together with DJs, dance showcases, street art battles, live performances, and hopscotch.
Cost: Free
Saturday - Sunday
Feb 10-11
Art Institute
This is advertised as "an unblushing look at nudity," but it's really just an excuse to giggle at scandalous stuff in public. Check out a naked dude wrestling a lion and a woman enjoying a golden shower from Zeus (among other bare-naked art) at this nudity-themed scavenger hunt at the Art Institute.
Cost: $38 (includes museum admission)
Saturday - Monday
Feb 10-19
McCormick Place
This annual exhibition of car porn features everything from futuristic new concept vehicles to boring old minivans at the nation’s largest auto show. Plus: the annual First Look for Charity preview event is always one of the fanciest nights of the year. The show first started in 1901 and has been running strong ever since.
Cost: $13
Sunday - Sunday
Feb 11-18
Various locations
Black Restaurant Week is a celebration of African-American culture, cuisines, and black-owned establishments in the Chicago area and its suburbs. Its goal is to highlight the history behind those restaurants and expose diners to delicious food from participating Chicago restaurants like Nadia’s Gourmet Grapes, Love Krave Cakes, Lem’s BBQ House, Haire’s Gulf Shrimp, and several others.
Cost: Prices and specials vary by location, but you can check out the full rundown at the official site.
Monday - Sunday
Feb 12-18
Various locations
This is a full week of cider-themed activities based on Saturday’s big Chicago Cider Summit at Navy Pier, with satellite events around the city including karaoke, dancing, dinner, and a post-summit hangover brunch.
Cost: Prices vary
Feb 14
Various locations
Whether you're seeing someone new or your love feels like a tale old as time at this point, you want only the best, most creative date for Valentine's Day. We've tried to make it easy by offering local suggestions and date ideas right here. Go on and be cute together; no one's looking.
Cost: Up to you and your Romeo or Juliet
Friday - Saturday
Feb 16-17
Music Box
Yes, this is an amateur porn festival, right here in our humble town. Watch porn in the company of strangers as the annual touring fest comes to Chicago with four sessions of short amateur porn that will change the way you look at adult entertainment.
Cost: $25 per session
Feb 17
Haymarket Pub
It’s an honest-to-goodness sausage fest at a local brew pub with 30+ house-made and guest sausages paired with 30+ beers and ciders, plus 10 cheeses. This event couldn’t be more Chicago if it tried.
Cost: $55
Feb 17
Empty Bottle
Gather outside the Empty Bottle for this annual winter tradition to rock live sets in the cold by ADULT., Thee Oh Sees, and B Boys. To further fuel your party, try the Goose Island beer, chili from the venue’s chili cook-off winner, and tropical tunes from Lumpen Radio DJs inside.
Cost: Free
Tuesday - Sunday
Feb 20-25
Various locations
Chicago’s festival of coffee beers expands to a full week of events in 2018, with a cocktail competition, roaster tours, chef’s beer dinner, and hangover party in addition to the main festival. This may be a pricey event, but for lovers of this fine subcategory of beer, there's no better pairing.
Cost: $65 per session for main festival; additional prices vary
Friday - Saturday
Feb 23-24
Logan Square Auditorium
Two nights of live music featuring local indie artists like Sidewalk Chalk and My Boy Elroy plus light shows, snow nymphs dancing, “artists at large,” and projection mapping = this winter throwdown. The best part? It helps raise funds for Chance the Rapper’s charity SocialWorks.
Cost: $25-$40
Friday - Sunday
Feb 23-25
One of the hottest parties of the seasons has expanded to three nights this year with live body painting, a free pancake bar, audio performances, and over 100 emerging artists showcasing their wares in a legendary local punk venue.
Cost: $10-$15
Saturday - Sunday
Feb 24-25
3514 N. Halsted
Warm up in a 6,000-square-foot heated party tent popping up in the middle of Boystown at this winter beer fest featuring local brewers like Revolution, Half Acre, and Pipeworks. In addition to the flowing suds, you can expect ice sculpture carving, DJs, and a rainbow light show.
Cost: $45-$50
Chicago Polar Plunge
Chicago Polar Plunge | Chicago PhotoPress
Mar 3
Hubbard & Wolcott
Join the teams of costumed freaks to race decked-out shopping carts through the streets at this Iditarod-inspired annual mobile food drive and scavenger hunt. It causes un-classifiably delightful chaos through Chicago neighborhoods late every winter, and it's a blast whether you want to watch or participate.
Cost: Registration fee TBA
Mar 3
Field Museum
Need an excuse to visit the Field Museum this winter? How about spring seasonal beers and specialty brews poured for VIPs to make this night at the museum infinitely more enjoyable than the Ben Stiller travesty? Just be sure to plan ahead: Tickets won't be sold at the door.
Cost: $45-$55
Mar 4
North Avenue Beach
This annual fundraiser for the Special Olympics includes “swimming” in the frigid waters of Lake Michigan, followed by a “melt down” party inside the North Avenue Beach boathouse with music and food. Shrinkage has never expressed itself so elegantly.
Cost: No registration fee, but there's a $200 fundraising minimum
Mar 17
As the unofficial end of winter in Chicago, one of the city’s most notorious day-drinking traditions features a green-dyed Chicago River and more green beer-amped idiots than the Beaumont at 4am. If you've never been in Chicago for St. Paddy's Day, you're in for a treat.
Cost: Free, but $40 for VIP seating