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9 adorable date ideas for wintertime in Chicago


We’ve all been there—sitting on the couch with our significant other and unanimously canceling date night. There’s nothing wrong with staying in, but when low temperatures turn you into a homebody, it can be refreshing to break out of the routine and bundle up to head out of the house. Resist the urge to let the Chicago winter snow on your romantic parade and keep the love alive with these winning winter 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 or $14 on weekends. When your legs need a break, enjoy a cup of hot chocolate and sit on a rink-side bench to take in the surroundings.

Warm up at a bar or restaurant with a fireplace. Gone are the summer days when you can spend afternoons on 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 find a cozy fireplace to cuddle up next to—you might even want to make a reservation.

Sip on some hot cocoa. Although Chicago has some great coffee spots, you can satisfy your sweet tooth with these delicious destinations for a classic cup of hot chocolate. A few have boozy twists to them, if you're in the mood for something a bit more potent.

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 offer 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.

Order delivery. If you just have to stay in, get delivery from one of these restaurants. Whether you’re craving pizza, burgers or cinnamon buns, there’s plenty of options. Cuddle up on the couch with your grub or set the table for a makeshift night out; whatever the case, picking some favorite delivery places is necessary to survive Chicago winter.

Get your game on. If you have a competitive side, Chicago is filled with indoor dives 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 cheap beer deals.

Test your wits with some bar trivia. Are you quick on your feet and armed with a wealth of random knowledge? Trivia is another competitive way to show off just how smart you are. Even if you don't come close to winning, pub quizzes make drinking more interesting and can be a good prelude to some cheap eats.

Numb the cold on a brewery tour. Chicago is known for its great craft beer, and there are breweries offering 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. If you're going to be stuck inside this winter, you might as well be laughing. From The Second City to iO, you can find a show on any night of the week for less than $20 per ticket.

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