Things to Do in Chicago This Winter

Photo credit Scott Olson / Getty Images

Extreme winter in Chicago challenges even the most hardened midwesterner. It might be tempting to hole up in your apartment or hotel room, huddling around a SAD lamp, but doing so would deny you all the great seasonal activities the city has to offer, outdoor and indoor adventures to raise the spirit and celebrate the holidays. Here are our favorite things to do to survive Chicago’s bleakest months.

Ice skate beneath the Bean

There are a bunch of places to skate around the city, but arguably the most iconic skating spot in Chicago is the rink at Millennium Park. The ice lays just below the famed Cloud Gate sculpture, making for one magical little circle of winter joy. Don’t worry if your skating skills aren’t up to par because all eyes will be on the beautiful cityscape anyway.
Millennium Park: McCormick Tribune Ice Rink

Drink your way to the Caribbean

Chicago may not be a tropical paradise, but you won’t remember that after a few drinks at one of the city’s primo tiki bars. Whether you head to Lost Lake in Logan Square or prefer Three Dots and a Dash downtown, there’s a rum drink ready to whisk you a few thousand miles away to the steamy shores of the Caribbean.

Take a nature walk (under glass)

All year round Garfield Park Conservatory treats visitors to a green wonderland, but the lush greenhouse is especially attractive in the depths of winter. The conservatory is often described as “landscape art under glass,” so skip the Art Institute and soak up some feel good art for the season.

Garfield Park Conservatory

300 N Central Park Ave, Chicago, IL 60624

Take a warm bath

Sure you could outfit your home tub with a few scented candles and put on some Sade for a relaxing evening at home alone, but if you want to truly renew your spirits, leave the bath to the professionals. The team at Air Ancient Baths spa are well versed in reversing seasonal depression, treating guests to hot baths, massages, and restorative beauty treatments.

Aire Ancient Baths

800 W Superior St, Chicago, IL 60642

Tear up Chicago’s best hills

Even if the weather doesn’t cooperate and the hills lay dry without snow far into March, the good folks of the Chicago Park District wheel out a snow machine to coat the hill by Soldier Field with fresh powder. So no matter what the forecast says, grab the kids, grab the sleds, and hit the slopes.

Order in from Chicago’s best butcher

Instead of risking a fall on the icy streets, bulk up on winter’s best sustenance with a delivery right to your door. Get a heap of meat from Publican to steel yourself against the bite in the air, hibernate until the stormy season passes, and don’t come out of your den until spring. It’s the healthy thing to do.

Publican Quality Meats

825 W Fulton Market, Chicago, IL 60607

Take in the holiday lights from above

You could drive around and see plenty of Christmas lights on the houses of Logan Square or Roscoe Village, or you could see literally all of the lights from a helicopter flying far above the streets. A number of companies run aerial tours in December for overachieving fans of seasonal light displays. From the sky, even Chicago’s biggest skyscrapers look like they’re lit up just to bring you holiday cheer.
Chicago Helicopter Experience