24 Hours In Chicago: Surviving Winter In The Windy City

Spending 24 hours Chicago is paradise… in the summer. You have gigantic lakes, beautiful weather, and some of the friendliest people in the world. Yet in the dead of winter, you could have epic snow, winds so cold they freeze your soul, and people who are more puffy jacket than man. Fear not though, if you are traveling through at this time, our Community Director Alex Shebar has some spots that will warm your heart and body. Pro-tip: you can follow and save this collection by opening 24 Hours in Chicago on mobile and click ‘follow’ once you’ve opened it in the Yelp app.

8 am: Welcome to Chicago! Now, run (don’t walk) to Whisk in Ukrainian Village, an amazing spot to start to day. Not only are the breakfasts epic (I recommend one monstrous plate of biscuits and gravy), but the whole cafe is modeled after the lifestyle (and look) of the mustached legend that is Mr. Ron Swanson. And if you’re scratching your head at the name, please skip the rest of this blog post and spend the rest of the day watching Parks and Rec. That’s not a suggestion, it’s mandatory.

Money Museum

10 am: Since it’s still freezing outside, best to spend a few hours getting cultured in a famous Chicago museum. Sure, you could go all Ferris Bueller and kill time in the Art Museum, but we say, why not go weird. Check out the International Museum of Surgical Science or the Money Museum (which is ironically completely free to visit). Both will leave you with things to learn and stories to tell.

1 pm: Lunch time! At this point, you’re probably craving a Chicago classic, and who could blame you. And when you want a classic, you’ve got to go with the classic spots. Head to Portillo’s for a “Polish” dog or Lou Malnati’s for deep dish pie. Listen, sometimes classics are classics for a reason. Just don’t blame me when you’re unable to do anything else for the rest of the day but nap.

2:30 pm: No, fight that urge. No time to nap. Let’s go! Fill your afternoon with something like axe throwing at Bad Axe Throwing, bowling at Southport Lanes, where they still have real people as pinsetters, or WhirleyBall, which is a combination of bumper cars, basketball, and lacrosse. 

Bad Axe Throwing

4 pm: Do you have to see The Cloud Gate (aka The Bean)? Fine, run through Millennium Park literally as fast as you can or you may freeze in place. The one advantage is that since it’s unbearably cold, you’ll probably be the only one out and you’ll be able to selfie like a boss.

5 pm: Obviously before dinner, we happy hour. You can find me at The Franklin Room, which is semi-hidden in a beautiful basement space. Beyond the food, which is truly delicious, they do some seriously killer $1 oysters every day from 5 to 6:30 pm. 

Au Cheval

6 pm: Do not. I say this again, do not leave this city without having a burger for dinner at Au Cheval. You can’t make a reservation so be prepared for a potential wait but then you can thank me after each bite. 

8 pm: At this point, you could do the traditional Second City for the famous improv or you can hop over to CSz. Two teams of ComedySportz comedians face off in ridiculous challenges to be the funniest in the room. No drink minimum and laughs at a maximum, it’s a damn good time.

10 pm: We’re not done with the fun. You’re going to need to grab nine friends and gather around the Killer Queen cabinet at Logan Arcade. It’s the world’s only 10-player arcade strategy game and it’s insane. Of course, you can’t take on that challenge without drink in hand, and luckily the arcade also has one hell of a beer selection. Game on!

12 am: Don’t be anywhere but Scofflaw at this time, and I’ll tell you why: they serve complimentary warm cookies for everyone at the stroke of midnight. Sure, their drinks are great and the kitchen stays open until 1 am, but seriously: ? ? ? .

1 am: Yeah, we checked outside – still damn cold. Better not even risk it and head to Watershed for their Warm Buttered Rum Cocktails. Hidden in the basement of Pops, this cozy spot is the perfect place to wait out the storm and drink until spring. Stay warm!