Date Ideas in Chicago for Winter

Couple embracing during winter

In love with walking in a winter wonderland? Or is curling up by the fire more your speed? If you’re looking for the best winter date ideas in Chicago, look no further! While the weather might have you wanting to hunker down like a hermit, you’d miss some of the most magical date ideas in Chicago. Winter is a great time to explore the city and relight an old flame or spark a new one, while ice skating or trying these places for the best winter dates in Chicago. 

Brunch and Games in the West Loop

For a fun, casual afternoon that tips its hat to the upscale, have a hearty brunch at the “James Beard” Award-winning chef, Stephanie Izard’s, Little Goat Diner. It’s more laid-back than Izard’s other Chicago restaurants, with the bustling vibe of a mid-century diner. Cozy up at the counter or enjoy the sun by the windows with a hearty brunch, and maybe get some cupcake to-go because you’re going to work up an appetite at any of the West Loop’s game options: classic arcade games at Emporium, bowling at Punch Bowl Social, or skateboarding at House of Vans are all great date ideas in Chicago’s winter months. 

Jazz and Noodles in Uptown

Another favorite date night idea for winter in Chicago involves warming up with a bowl of noodles along Asia on Argyle. Great Vietnamese restaurants dot this stretch of uptown and include hip joints like Tank Noodle and mom-and-pop spots like Nha Hang. When you’re finished slurping, experience a Chicago classic: an evening of jazz at The Green Mill Cocktail Lounge. Al Capone’s former hangout has been slinging drinks for over 110 years. With low lights and close booths, it’s a great way to get better acquainted. Bring cash to buy your date an Old Fashioned, though, because The Green Mill doesn’t take credit cards. 

Views and Shakes Downtown

Make a reservation to experience the thrill of seeing Chicago from 103 stories above the city at the glass-floored Ledge at the Skydeck in Willis Tower. Once you’ve felt the shake and sway that comes with being at the top of the tower, zoom down to the main floor and reward your courage with burgers and shakes from Shake Shack, or any of the other restaurants located in Catalog, with four floors of shopping and entertainment. Get it to go, so you can browse the shops. 

Music and Whiskey by the Fire in Lincoln Square

Tucked into the northside, Lincoln Square is perfect for music lovers in love. Browse the LPs at Laurie’s Planet of Sound, then take in a performance or take a workshop together at the Old Town School of Folk. Then get toasty by one of the neighborhood’s pub fireplaces with a whiskey at Fountainhead, or the renowned burger at The Grafton

Art and Carnitas in Pilsen

Brighten up a gray winter day with a visit to the National Museum of Mexican Art in the Pilsen neighborhood. The permanent collection is over 11,000 pieces, making it one of the largest collections of Mexican art in America in intimate galleries. Discuss your favorite pieces of art over a warm and spicy dinner at any of the nearby authentic Mexican restaurants like 5 Rabanitos, Birrieria Reyes De Ocotlan Restaurant (cash only), or Taqueria Los Comales.

Enjoy These Date Night Ideas in Chicago and More! 

No matter which date ideas in Chicago you choose this winter, know that you can always contact Skydeck for more ideas on the best ways to experience Chicagoland at any time of year!