Events

13 Things You Absolutely Must Do in Chicago This Winter

Published On 12/17/2015 Published On 12/17/2015
Flickr/Dan Mullen

Date

Event

Location

Dec 31 Thu

Ring in 2016 with booze AND a marching band Toast your fresh start to the new year (and impeding couch-ridden New Year's Day) with a performance by Mucca Pazza at the Chicago Athletic Association. The 20-piece band will be joined by a roster of guest DJs with a special toast at midnight. Consider this safe harbor from all the terrible people you'd otherwise have to deal with on Michigan Ave that night.

Chicago Athletic Association Hotel

Ring in 2016 with booze AND a marching band Chicago Athletic Association Hotel Toast your fresh start to the new year (and impeding couch-ridden New Year's Day) with a performance by Mucca Pazza at the Chicago Athletic Association. The 20-piece band will be joined by a roster of guest DJs with a special toast at midnight. Consider this safe harbor from all the terrible people you'd otherwise have to deal with on Michigan Ave that night.

Date

Event

Location

Jan 7-17

Catch T.J. Miller and Danny Pudi at SketchFest This year, the world’s largest sketch-comedy festival brings together 165 groups for 186 shows over eight days. If you can’t find something to laugh about here, congratulations: you must be a robot. Scientists should study you.

Stage 773

Catch T.J. Miller and Danny Pudi at SketchFest Stage 773 This year, the world’s largest sketch-comedy festival brings together 165 groups for 186 shows over eight days. If you can’t find something to laugh about here, congratulations: you must be a robot. Scientists should study you.

Flickr/goatling

Date

Event

Location

Jan 13-17

Rock out at Chicago’s SXSW during Tomorrow Never Knows It’s just like SXSW, minus the 70-degree weather and 6th St face-plants. Taking place throughout the city at venues including Schubas, Lincoln Hall, Hideout, and Metro/Smart Bar, this year’s highlights include the indie sounds of Dinosaur Jr. founding member Lou Barlow and the “what the hell was that?” sounds of veteran comic Bobcat Goldthwait.

Various locations

Rock out at Chicago’s SXSW during Tomorrow Never Knows Various locations It’s just like SXSW, minus the 70-degree weather and 6th St face-plants. Taking place throughout the city at venues including Schubas, Lincoln Hall, Hideout, and Metro/Smart Bar, this year’s highlights include the indie sounds of Dinosaur Jr. founding member Lou Barlow and the “what the hell was that?” sounds of veteran comic Bobcat Goldthwait.

Vanessa Belfiore / Shutterstock.com

Date

Event

Location

Jan 15-17

Buddy up to the players at this year’s Cubs Convention There hasn’t been this much excitement around a Cubs Convention since... well, last year. This year’s event brings the 2015 season’s buzz to a crescendo at the Sheraton Grand in River North and is your best chance to get up close and personal with the players and coaches. Short of shelling out thousands for playoff tickets, that is.

Sheraton Grand

Buddy up to the players at this year’s Cubs Convention Sheraton Grand There hasn’t been this much excitement around a Cubs Convention since... well, last year. This year’s event brings the 2015 season’s buzz to a crescendo at the Sheraton Grand in River North and is your best chance to get up close and personal with the players and coaches. Short of shelling out thousands for playoff tickets, that is.

Sean Cooley/Thrillist

Date

Event

Location

Flickr/BurnAway

Date

Event

Location

Feb 5-6

Get your body painted while housing pancakes at the Pancakes & Booze Art Show Chicago’s largest underground art show features live body painting, a free pancake bar, live performances, and displays from 90+ emerging artists. So yeah, it’s kind of fun.

Reggies

Get your body painted while housing pancakes at the Pancakes & Booze Art Show Reggies Chicago’s largest underground art show features live body painting, a free pancake bar, live performances, and displays from 90+ emerging artists. So yeah, it’s kind of fun.

Flickr/Ron Brickman

Date

Event

Location

Feb 13-21

Date a model at the Chicago Auto Show By now you know what to expect from the nation’s largest auto show: cars, models, and one of the swankiest evenings of the year at the annual pre-fest gala First Look for Charity. Maybe bring along one of those models.

McCormick Place

Date a model at the Chicago Auto Show McCormick Place By now you know what to expect from the nation’s largest auto show: cars, models, and one of the swankiest evenings of the year at the annual pre-fest gala First Look for Charity. Maybe bring along one of those models.

Flickr/Kmeron

Date

Event

Location

Feb 14 Sun

Spend Valentine’s Day with one of the best weirdo bands imaginable Forget the flowers and candy. Nothing says “I love you” like taking your special someone to see a rare live set from legendary Canadian experimental rockers Godspeed You! Black Emperor at Thalia Hall. Grab some punch afterward.

Thalia Hall

Spend Valentine’s Day with one of the best weirdo bands imaginable Thalia Hall Forget the flowers and candy. Nothing says “I love you” like taking your special someone to see a rare live set from legendary Canadian experimental rockers Godspeed You! Black Emperor at Thalia Hall. Grab some punch afterward.

Flickr/Bing

Date

Event

Location

Feb 21 Sun

Bring extra napkins to Chicago’s Best WingFest The city’s top wing-slingers douse the West Loop in sauce, competing in the categories of mild, hot, BBQ, and exotic. Plus, there's live music and tossed-out T-shirts. Pro tip: bring napkins. Or use one of those shirts.

Bailey Auditorium

Bring extra napkins to Chicago’s Best WingFest Bailey Auditorium The city’s top wing-slingers douse the West Loop in sauce, competing in the categories of mild, hot, BBQ, and exotic. Plus, there's live music and tossed-out T-shirts. Pro tip: bring napkins. Or use one of those shirts.

Flickr/Jenni Konrad

Date

Event

Location

Feb 21 Sun

Road trip to Minneapolis to see the Hawks dominate the Stadium Series Chicago winter not cold enough for you? Then head to the Great White North of Minneapolis to see the Blackhawks take on the Minnesota Wild outdoors in one of two NHL Stadium Series games this year. We’re not responsible for frostbite.

TCF Bank Stadium

Road trip to Minneapolis to see the Hawks dominate the Stadium Series TCF Bank Stadium Chicago winter not cold enough for you? Then head to the Great White North of Minneapolis to see the Blackhawks take on the Minnesota Wild outdoors in one of two NHL Stadium Series games this year. We’re not responsible for frostbite.

Flickr/Milosh Kosanovich

Date

Event

Location

Mar 5 Sat

Race shopping carts through the street at this year’s CHIditarod Chicago winter wouldn’t be Chicago winter without the CHIditarod, the annual urban mushing contest that has costumed teams racing shopping carts full of donated food around Wicker Park/Ukrainian Village. You can even win an award for “Best Sabotage,” if you’re feeling frisky.

Wicker Park/Ukrainian Village

Race shopping carts through the street at this year’s CHIditarod Wicker Park/Ukrainian Village Chicago winter wouldn’t be Chicago winter without the CHIditarod, the annual urban mushing contest that has costumed teams racing shopping carts full of donated food around Wicker Park/Ukrainian Village. You can even win an award for “Best Sabotage,” if you’re feeling frisky.

Flickr/kate gardiner

Date

Event

Location

Mar 13 Sun

Try to behave yourself at the South Side Irish Parade While not quite the booze-soaked embarrassment it once was, some things remain traditions for a reason. And (green beer notwithstanding) this iconic Beverly parade remains one of the best.

Western Ave from 103rd to 115th St

Try to behave yourself at the South Side Irish Parade Western Ave from 103rd to 115th St While not quite the booze-soaked embarrassment it once was, some things remain traditions for a reason. And (green beer notwithstanding) this iconic Beverly parade remains one of the best.

Flickr/Mandy

Date

Event

Location

Mar 18-20

Say goodbye to winter by dressing like a sexy Stormtrooper at C2E2 This year, the last few days of winter also happen to coincide with the annual Lollapalooza for dress-up fantasy nerds. Mingle with a who's-who of comic-industry elite and plenty of random “celebrities” like Cliff Clavin from Cheers, plus panels and screenings, the country’s largest cosplay tourney, and copious costumed afterparties.

McCormick Place

Say goodbye to winter by dressing like a sexy Stormtrooper at C2E2 McCormick Place This year, the last few days of winter also happen to coincide with the annual Lollapalooza for dress-up fantasy nerds. Mingle with a who's-who of comic-industry elite and plenty of random “celebrities” like Cliff Clavin from Cheers, plus panels and screenings, the country’s largest cosplay tourney, and copious costumed afterparties.

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