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Crank the heat on your next date night with the most romantic things to do in Chicago
Written byTime Out Chicago editors Thursday January 14 2021
Believe it or not, Chicago is brimming with romance. And possibly even more so for all the amorous pleasantries that go unseen during our brutal winters—in sweatpants, under blankets in our heated apartments with Netflix rolling in the background. Aside from keeping each other warm, there are oodles of romantic things to do in Chicago. When we’re looking to crank up the heat on date night, we order in from some of the best restaurants in Chicago, explore the city’s many lush green spaces, and gaze longingly at the dazzling skyline. Sometimes it just takes a fresh perspective to turn even the most mundane activity into one of the most romantic things to do in Chicago. Whether you’re celebrating Valentine’s Day in Chicago or you’re just looking to liven up a Friday night, these romantic things to do in Chicago should do the trick.
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The most romantic things to do in Chicago
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1. Order takeout for date night at home
Without a doubt, one of the most romantic things to do in Chicago is dining out for date night. Even though restaurants and bars are closed for dine-in service, you can still replicate that experience at home (and support local businesses while you’re at it). Plus, you can stay in your pajamas if you want to. Opt to keep it casual with pizza or burgers or go all out with a multi-course meal from one of the city’s top fine-dining destinations. Don’t forget to toss in a bottle of wine to up the ante.
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2. Tackle these hiking trails together
If spending time together typically revolves around being active, there are plenty of wide open spaces to explore beyond your neighborhood. Our city doesn’t boast nearby mountains like Seattle or San Francisco, but what the Midwest lacks in elevation it makes up for in natural beauty. Head to the city’s Northwest Side to go for a walk on the North Branch Trail, head west to trek through the suburbs on the Illinois Prairie Path Trail or cross state lines to visit the gorgeous Indiana Dunes along Lake Michigan.
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3. Spend the night at a romantic hotel
Planning a romantic weekend away doesn’t mean that you have to leave town. In fact, there are so many romantic hotels in Chicago that you probably don’t even need to hop in the car. They boast luxurious amenities, in-room dining from some of the best restaurants in Chicago and jaw-dropping views—everything you need to set the mood. A deep tub and fluffy robes don’t hurt either. Pack your overnight bag and prepare for a night away at the most romantic hotels in Chicago.
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4. Hold hands at the Maggie Daley Park Skating Ribbon
If you don’t mind sharing the ice with a few kiddos, dust off your ice skates (or rent a pair onsite) and hit the winding rink at Maggie Daley Park in the heart of downtown Chicago. Hold your honey’s hand as you make your way around the circular path set against skyline views. Don’t forget: you’ll need to plan ahead and make a reservation online if you want to get on the ice.
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5. Scope out the best public art in Chicago
Chicago is home to some of the best museums in the world, but if you know where to look, the city is an art gallery in and of itself. From towering sculptures by the likes of Picasso and Calder in the Loop and breathtaking murals by local artists such as Hebru Brantley and Hector Duarte in Pilsen, you can spot beautiful creative works in all corners of the city. Take your special someone on a scavenger hunt to find it all.
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6. Take a dip at Aire Ancient Baths
Breathing new life into the ancient tradition of Greek and Roman bath houses, Aire Ancient Baths is a singular spa experience that can be enjoyed solo or with a partner. Book a couples massage or body treatment and make time to explore the spa’s different baths, which vary from ice-cold to steaming hot.
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7. Grab a bottle from a top-rated wine shop
Spending the night at home doesn’t mean that you have to compromise on booze. In fact, with a helping hand from the best wine shops in Chicago, you can sip and swirl like you’re dining at one of the city’s finest restaurants. There’s a wine shop in Chicago for every budget, craving and occasion, whether you’re stocking the fridge with $10 bottles or looking for something to impress your wine-loving partner.
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8. See a virtual show at the Hideout
You can still plan a night “out” without actually leaving the house thanks to the Hideout’s virtual programming calendar, which is packed with happy hours, concerts and album release parties. Simply choose the show you want to attend, pay a small admission fee (usually $5–$10) and tune in at showtime. Like what you see? Upgrade to a subscription ($25 a month) so that you and your partner can hop from show to show whenever you’d like.
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9. Steal a kiss at Promontory Point
There’s a good chance that you know at least one person who has considered getting hitched on Promontory Point, a man-made peninsula on the shore of Lake Michigan. Accessible via the Lakefront Trail, the park boasts amazing views of the Chicago skyline and a field house that could be mistaken for a small castle. No matter the season, there’s something wonderfully romantic about the South Side lakefront spot.
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10. Upgrade your Netflix routine with Music Box Theatre
For movie lovers who don’t care for traditional Hollywood blockbusters, there’s no better theater than the Music Box, a two-screen cinema that shows the latest art-house films and documentaries. Sadly, the theater is closed to the public at the moment, but its Music Box at Home program gives you access to a range of streaming movies. Snuggle up on the couch with your significant other and watch a new release while supporting one of Chicago’s most important cinemas.
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11. Get your nightcap to go
If you’re anything like us, you miss holing up at a dark, sexy bar until the wee hours of the morning. We can’t do anything to improve the vibe of your apartment, but the best bars in Chicago can help you out with boozy provisions. Take a look at some of the best hot cocktails and mulled wine available around town right now, and turn up the temperature this weekend.
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12. Get lost in the Garden of the Phoenix in Jackson Park
Initially designed by Frederick Law Olmsted for the World’s Columbian Exposition of 1893, Jackson Park is one of the city’s crown jewels. But perhaps its most enchanting section is the Garden of the Phoenix, a Japanese strolling garden on Wooded Island. Formally known as the Osaka Garden (for Chicago’s sister city), the grounds now feature a permanent art installation by Yoko Ono. It’s the perfect place to saunter through with someone special.
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13. Pick up sweets for your sweetheart
Nothing says romance quite like a box of macarons or a picture-perfect tart. If you want to do something sweet for your S.O., swing by one of the best bakeries in town to pick up an array of sugary confections to enjoy at home.
On a budget?
Amazingly cheap things to do in Chicago
Chicago, we love you, but you can be pretty damn expensive (hello, $15 cocktails and pricey cover fees). Even so, you don’t have to blow the bank to have a good time in the city—as long as you know where to look. Follow our lead.
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