Things to Do in Chicago this Winter

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It may be cold in Chicago and oddly foggy but there’s no such thing as winter blues here. 

Staying under the covers, warm and cozy may have sounded nice before but after reading the list below you’ll be putting on the parka and heading out the door in no time.

Sharing my top things to do in Chicago this winter below so get your snow gear ready to put on and enjoy!


Top Things to Do This Winter


Dance the night away with Sue. 

One of Steve and I’s favorite date nights are attending galas together. Nothing beats getting all dressed up, meeting new people and dancing the night away. Last year, we attended the Snowball for the first time and raved about it to friends all year long. It’s our favorite gala to date; dancing, drinks and bites at the Field Museum and best yet, the evening benefits Lurie Children’s Pediatric & Adolescent HIV/AIDS Program. You can bet you’ll find us there again this year! For more information on how to purchase tickets visit here.  

Gather the friends for a Game Night.

Nothing beats getting a group of friends together for a game night and with game bars popping up all over the city, you don’t have to do game night at home with a deck of cards and a case of beer anyone. Some of my favorite spots include Point & Feather, Acebounce, Game Room at the CAA and Gunthrie’s Tavern.

Escape the snow and take a dip at Aire.

Pull the swimsuit out from the storage bin and take at dip at the city’s newest bathhouse, Aire.

Eat your way through the city during Restaurant Week.

Whether it’s weekend brunch or date night dinner, enjoy a pre-fixe meal at any of the city’s hottest restaurants during Restaurant Week. For more information, visit here.

Laugh away the winter blues at Second City.

I know I include this on every Chicago guide but that’s how much I love this place! Every show is unique and each time is a new act or cast. Some of country’s top comedians have come out of Second City and if you go there you can see why.

Get outdoors and skate the ribbon at Maggie Daley Park.

No need to only stay indoors, head outside and do a lap or five at the new skating ribbon at Maggie Daley Park. Enjoy breathtaking skyline views while skating in the heart of downtown.

Indulge in deep fried dough at Donut Fest.

Enough said. For more information and tickets, visit here.

Sip on hot cocoa at XO Marshmallow.

Cute, colorful and out of this world flavor combinations. Enjoy a glass of your not so average hot chocolate with homemade marshmallows at this adorable cafe. 

Museum hop during free days.

Be a tourist in your own city or be a tourist if you’re a tourist and enjoy free days at city’s top museums. Full schedule here

Enjoy movie night with the AMC monthly movie pass. 

If you’re movie buffs like Steve and I, then you probably find you spend just about as much on movies as you do at the grocery store these days but not for much longer. Grab the popcorn and keep your wallet at home with this unlimited $10/month movie pass. For more information for theaters near you, visit here

Pretend it’s summer again at Summer House or Somerset.

Fake it until you make it or just grab a drink/food at one of these summer themed restaurants that will have you counting down the days until patio season.

Break a sweat at one of the many new studios in Chicago.

No hibernation season here. Grab the gym bag and head to your local studio for a winter sweat. Some of my favorites currently are Studio Three, Flywheel and Core Power.

Grab a drink or some bites and cozy up to the fireplace. 

Not your fireplace (if you’re lucky enough to have one of those in the city) but one of these warm and cozy restaurants that will have you never wanting to leave. 


What are your favorite winter activities? Anywhere new you discovered this year that has become a go-to?









2 thoughts on “Things to Do in Chicago this Winter

  1. Jess Zimlich

    Visiting AIRE and ice skating are both on my winter bucket list! And I’ve been posting up at CAA during the day with my computer, but I want to go back for a game night and drinks now!

    1. Megan | Blog Appetit Post author

      Me too! I’ve done ice skating but I haven’t gotten a chance to see Aire in person so if you go let me know! Also, I was there the other day for an event and thought why don’t I ever work from here? That lobby is unreal! I may have to join you next time;) Have a great weekend!


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