Best Things to do in Chicago in Winter

I love sharing my recommendations for all of the places I travel to, so much so that I often forget about my own backyard! While I absolutely despise the cold, Chicago offers so much to do that it makes “Chiberia” tolerable. I hope you can enjoy some of my favorites during a winter visit, or just a day out in the city!

Things to Do in the Winter: 

See a Broadway Show: From Wicked to Cats to Les Misérables, there’s always something exciting happening on Broadway in Chicago’s.

Ice Skating: Ice Skating in the heart of downtown Chicago is a classic winter activity. We’re lucky to have two amazing skate rinks at Millennium Park: the McCormick Tribune Skating Rink and The Maggie Daley Ribbon. Admission is free, but online reservations are required. Skate rentals are available.

Art Institute: Chicago’s Art Institute is obviously great all year round, but it’s especially nice to walk around and enjoy the museum’s massive collection when you want to escape the cold (PS. Even if you don’t go in, be sure to check out the Lions guarding the museum- they have holiday wreaths on every holiday season.)

Driehaus Museum: OK, before you roll your eyes because I put a museum on here…the Driehaus is FABULOUS. It’s a gilded age mansion with an incredible collection of antique furniture, Tiffany glass works, and tapestries. It’s rather small and cozy, making it a perfect place to stop in on a winter day.

Glessner House: Similar to the Driehaus Museum, the Glessner House is a historical landmark home. Completed in 1887, it houses all of the furniture and decorations of the Glessner family from that time. During the holidays, the Glessner House offers a lovely Christmas candlelit tour of the home, which is decorated in traditional Christmas decorations true to the late 1800s.

Lyric Opera: Put on your opera gloves and a fancy fur coat, and spend an evening at the Opera! Chicago is lucky to have one of the best Opera companies in the world, and it’s worth a visit.

Mag Mile: Shopping on the Magnificent Mile during the holidays is always a classic. Bundle up, grab a hot chocolate at Ralph’s Coffee (attached to the Ralph Lauren store) and enjoy the Christmas lights up and down Michigan Ave while you shop.

Chicago Magic Lounge: This is one of my favorite indoor date nights. The Chicago Magic Lounge is part speakeasy, part magic theater, and a whole lot of fun!

Best Christmas Activities

Hotel Lobbies: Chicago’s upscale hotels really go all out for Christmas, and bopping into hotels to see their Christmas decorations makes for a lovely way to warm up when you’re out and about in the winter. I especially adore the decorations at The Peninsula and the Drake Hotel.

Zoo Light’s at Lincoln Park: A Chicago holiday tradition, the Lincoln Park Zoo is sparking with Christmas lights November through January. It’s $5 per person (free on Mondays) and great for families.

The Nutcracker at the Lyric Opera: If you’re visiting in December and prefer the ballet to the opera, you can catch a performance of the Joffrey Ballet’s Nutcracker at the same beautiful location.

Christkindlmarket: If you’re visiting before Christmas, you can stop by Chicago’s Holiday market for a warm mug of mulled wine, and some Christmas shopping! It does get crowded, so I recommend visiting during weekdays.

Christmas Pop Up Bars: Holiday pop up bars are quite popular lately. From Frosty’s to the Nutcracker Pop Up, it’s a cheesy but certainly festive way to spend an evening!

Coziest Restaurants

Bavette’s or Gibson’s: Great options if you’re looking for a classic Chicago Steakhouse.

Ciccio Mio: Tiny, gorgeous Italian spot. It’s romantic, and our go to for celebrations.

Trivoli Tavern: I love Trivoli year round, but in the winter it’s especially lovely. It’s so cozy and beautiful, and their old school Italian menu will warm you right up.

RL Grill: The restaurant at Ralph Lauren is one of my favorite in the city. It’s cozy and très chic. It’s the perfect way to end a day of shopping on Michigan Ave. 

Chicago Pizza and Oven Grinder Co: Chicago is known for it’s deep dish pizza, but this place takes it a step further with a break bowl full of pizza fillings. Cozy and indulgent, a visit to Oven Grinder is a nice treat after a stroll through Lincoln Park’s Zoo Lights!

Armitage Alehouse: Don’t let the name deceive you, it’s really beautiful inside! A little farther north than most of my suggestions.

Au Cheval: Chicago’s revered burger spot.

Coziest Bars

The Milkroom: An 8 person former speakeasy, with rare bottles. Heavier on dark spirits.

Gilt Bar, The Library: These two bars are located practically side by side and both offer an intimate, dark, cozy and romantic vibe.

Wilde: A “literary-themed upscale Irish pub”. I will leave it there.

Green Mill: If you’re looking for live jazz, the Green Mill is a Chicago classic. Note that it’s far north, cash only, and doesn’t accept reservations.

The Bassment: A great option for live music and dancing!