Winter In Chicago

For us Chicagoans we’re good at accepting the cold weather up until like two seconds after New years. Then it’s count down to Spring. October, November & December are cold but there’s Farmers Markets, holiday lights, the Christkindle Market, shopping…all to take our mind off the fact that we gotta remember what we did with our gloves and long underwear from last year. 

It’s January 1st. You’ve now scrubbed the last of the New year’s glitter off of your body and you’re ready to shake off the hangover and get that gym membership right? Living in Chicago, January till whenever it gets tolerable outside is usually a time for me to get organized and prep for warm weather. Time to clean out that junk drawer, clean out the closet, tinker with some electronics, hang some new pictures, edit that lost video footage from the summer… 

All of that stuff is great to get done while it sucks outside. No one want to have to do any of those chores when it’s nice out. No nice day in Chicago should be spent indoors. But what about those winter days where you want or just need to get out of your house, apartment or condo? Or you are just moving here or on a business trip and want to find something to do. Or maybe you have been to Chicago in the summer but what to see what it’s like in the winter. Sure why not, right? There’s actually a ton to do in the winter. Just dress warm and the city is yours. 

What’s it like outside?

having a fun day in Chicago heavily depends on how you dressed for the day. Check the news or your favorite weather app to see what the temperature is going to be. If you are coming in from the burbs there could be a big difference from where you are at verses Chicago, especially along the lakefront.

My feet Hurt!

If you are going to be doing a lot of walking make sure to wear comfortable shoes. Flips flops might be comfortable to run (drive) to the store and back but are you really going to be comfortable in those putting in some miles? If there’s snow and ice make sure you have some good footwear for that too.

Awww man I forgot my?

Forget or lost your hats or gloves? Need some new socks because yours are soaked. Hit up a Walgreens for these. You can usually get something fairly decent there too. It will be much quicker than hitting Marshall Fields or whatever they call it now!


Maybe you left or lost those gloves on purpose! Maybe you want to do a little shopping. Macy’s in the Marshall Fields building has just about everything that you can think of. Also, even when it’s cold out, walking down Michigan Ave. (AKA Magnificent Mile but no one that lives here actually calls it that) always feels so nice, we’ll maybe with the exception of a Saturday right before Christmas.

Here’s some suggestions and favorites of mine. 


Chicago has some amazing museums. Like ones you actually want to go to. The wintertime is the perfect time to go too. It get’s you out of the house and you’ll get some exercise while you are at it. You might even learn a thing or two.

John G. Shedd Aquarium

The “Shedd Aquarium” is definitely my favorite of all the museums. Maybe because there’s living animals there. That being said, can this be considered a museum? We’ll it’s on The Museum Campus, so I’m gonna say YES!

The big aquarium at the entrance and the Amazon are just gorgeous. I also like to go exploring around the lower level. I always seem to find some area that I never saw before down there.

Pro Tip:

Take the bus or walk. Parking can be rough around here. If you are not use to hunting for parking you’re gonna get frustrated. If you get there early and especially in the winter you will have a good chance for parking. Also make sure to get a skyline pic from the entrance. I take one every time. Also walk around the lake side of the Shedd. You’ll really see how big Lake Michigan is.

Get on TV

WGN’s man Of The people films at the famed WGN Studios.


Go explore the underground Pedway in downtown Chicago.

Auto Show

Chicago is home to the nations largest auto show. Held every year at McCormick Place.

RV Boat & Sail Show

Also at McCormick Place, there’s a full day of looking at boats and RV’s. You will be able to go in to them as well. The dealers are ready to sell on the spot. Sometimes with some huge discounts!

Thinking about summer road trips in a RV or the open water in your new boat? Or just wanna get out of the house and dream a little?

I got Dibs… You’re going to see this if you are in Chicago during the winter.