13 Winter Date Spots in Chicago

In the middle of winter, it’s easy to get stuck in a rut. When it’s near zero degrees and ultra snowy, I personally don’t have much desire to leave home and explore the city, or venture beyond my nearby 3 or 4 same places. (Anyone else?!) Thankfully, we’re getting past the ‘midwinter’ point and each sunny day helps beat those winter blues. That said, winter isn’t all that bad! Some of my favorite places in the city are most memorable during the winter months and have offered amazing experiences over the years. So, in the spirit of Valentine’s Day — and getting out there and making the most of our city! — I gathered a dozen of my favorite Chicago spots for winter dates. (Galentines included, too.)

GARFIELD PARK CONSERVATORY  |  This place gives you the feeling of an escape from the city (and the harshness of winter). Browse an impressive array of plants, flowers and exhibits indoors and learn a thing or two.

LIBRARY AT AMBASSADOR  |  The Library Bar is located at the other side of the Ambassador Hotel across Pump Room. It feels sophisticated yet relaxed, with a large fireplace anchoring the space.
CHICAGO THEATRE  |  There’s always something going on at the Chicago Theatre. You probably know it’s iconic exterior, and inside you’ll find everything from live music to stand-up comedy.
3 ARTS CLUB CAFE  |  The ambience here is spectacular. You can grab a table for seated lunch in the main courtyard, or what I prefer to do is order coffee (or wine), browse RH, and cozy in on a sofa.

ART INSTITUTE  |  The Art Institute is perhaps my favorite place in the city to visit. Along with the classics, there are always rotating exhibits and new pieces to discover. (p.s. Thursday evenings are free for Illinois residents.)

MILLENNIUM PARK RINK  |  Bundle in layers, lace-up in skates, sip hot cocoa and hit the ice. There’s something magical about ice skating and seeing the skyline lights all around you.

THE GRAY  |  Okay, this is a new one. The Gray Hotel just recently opened its doors downtown and is stunning. Cocktails and conversation at Vol. 39 sounds perfect to me.

LE COLONIAL  |  Le Colonial is one of my favorite restaurants in Chicago. It’s located in the Oak Street district, and always delivers top service and delicious French Vietnamese cuisine.

GREEN MILL  |  I have a big heart for jazz and don’t go here nearly enough. The Green Mill has been a Chicago institution for almost a century. Check the website for a calendar of performers and enjoy.
RM CHAMPAGNE  |  Tucked away in an alley off Green Street, RM has an amazing patio (for summer) and a cozy indoor space. They serve — well, champagne — and more. Try to go soon after opening hours or on a weekday to beat the rush.

DAVIS THEATER  |  Who doesn’t love going to the movies? Located in Lincoln Square, The Davis originates from 1918 and recently went through new renovations. There’s a variety of spots nearby for pre or post-movie dining, too.

REVOLUTION BREWING  |  Chicago has a lot to offer in the craft beer scene. Revolution Brewing hosts brewery tours and sampling at its Brewpub. (We’re a fan of Anti-Hero in our household.)

EATALY  |  If you’re unfamiliar, Eataly is a big Italian marketplace with cafes, counters, and a cooking school. I say it’s best to visit on a weekday, to avoid busy weekends. Enjoy a glass of wine, along with a charcuterie plate and dessert.

What are your favorite winter date spots in Chicago, or in your hometown?
Image by Jenny Connors

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