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9 adorable date ideas for when the temperature drops in Chicago

Written by
Stephanie Bernstein

We’ve all been there—sitting on the couch with your significant other and unanimously cancelling date night. There’s nothing wrong with staying in, but when low temperatures turn you both into homebodies, break out of the routine and bundle up. Resist the urge to let the Chicago winter rain on your romantic parade and keep the love alive with these adorable wintry date ideas.

Try out the ice skating ribbon at Maggie Daley Park. Show off your skating skills (or lack thereof) with the city’s skyline as your backdrop. Admission is free if you bring your own skates, otherwise it’s $12 to rent a pair ($14 on weekends). When your legs need a break, enjoy a cup of hot chocolate and sit on a rinkside bench to warm up.

Warm up at a bar or restaurant with a fireplace. Gone are the summer days where you Google search local places with outdoor patios; instead, you’re sticking out an hour-long wait to sit indoors. If you’re planning to dine out for date night, do yourself a favor and check this list ahead of time—maybe even make a reservation. Your date will appreciate it.

Sip on some hot cocoa. Although Chicago has some great coffee spots, satisfy your sweet tooth with these delicious destinations for a classic cup of hot chocolate. A few have boozy twists to them, so this first cocktail could start off the rest of your evening right.

Have a night at the museum. Many local museums host events in Winter to help Chicagoans escape the cold—Adler Planetarium hosts Adler After Dark, a monthly, full-access event for adults 21+ only. Some museums even have free admission on certain days in December, January and February—The Field Museum offers two free admission days monthly and additional deals for Illinois residents. Appreciate some culture on your date if you haven’t already taken your out-of-town guests to these spots one hundred times.

If you just have to stay in, order in delivery from one of these restaurants, thanks to DoorDash. Whether you’re craving pizza, burgers or cinnamon buns, there’s plenty of options so you don’t have to limit yourself to late-night Chinese food from the shop on the corner. Cuddle up on the couch with your grub or set the table for a makeshift night out; whatever the case, ordering in is necessary to survive the winter.

Get your game on. If you have a competitive side, there are indoor bars where you and your date can face off. Emporium Arcade Bar has throwback video games and plenty of craft beers to sip on during your air hockey showdown. Closer to the Loop, SPiN has ping-pong tables, giant Jenga and other board games complemented by great cocktails and comfy couches. Or, bet on turtle races. Every Friday night, both Big Joe's and Tin Lizzie host turtle races with beer deals. They can get rowdy, so get your spot early.

Test your wits with some bar trivia. Are you quick on your feet and have a knowledge of random facts? Trivia is another competitive way to show off to your date. Even if you don't come close to winning, pub quizzes make drinks more interesting.

Numb the cold on a brewery tour. Chicago is known for its great craft beer, and breweries offer tours in pretty much every corner of the city. Share a few tasty flights and develop a nice daytime buzz that will keep you protected from the frigid temperatures.

Chuckle away your frostbite at a comedy show. It's no secret that Chicago is an amazing comedy city. If you're going to be stuck inside this winter, you might as well be laughing. From The Second City to iO to UP Comedy Club, you can pretty much find a show any night of the week for less than $20 per ticket.

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