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Photograph: Courtesy Langham Hotels & Resorts

22 romantic things to do in Chicago

Crank the heat up on your next date with these fun and romantic activities.

Jeffy Mai
Written by
Jeffy Mai
&
Time Out Chicago editors
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Believe it or not, Chicago is brimming with romance, even in the coldest months. Aside from keeping each other warm, there are tons of romantic things to do in Chicago. When we're looking to elevate date night, we take dips in thermal baths, explore the city's many lush green spaces, attend laugh-out-loud shows and dine at the most romantic restaurants. Some of the best things to do in Chicago can also be a perfect bonding experience. So whether you're going on a first date or just looking to liven up a Saturday, these romantic things to do in Chicago should do the trick.

RECOMMENDED: The best romantic hotels in Chicago

The most romantic things to do in Chicago

  • Restaurants

There’s no shortage of romantic restaurants in Chicago to wine and dine your partner at. You’ll find dimly lit spots, fondue feasts, rooms with beautiful views and many more intimate options. They all know how to set the mood so that couples can have a lovely and unforgettable experience. The food’s obviously stellar, too, featuring everything from French and Italian cuisine to dry-aged steaks.

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Jeffy Mai
Editor, Time Out Chicago
  • Hotels

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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  • Attractions
  • Parks and gardens
  • Millennium Park

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.

  • Health and beauty
  • River West/West Town

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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  • Comedy

One of the quickest ways to win someone’s heart is to make them laugh. Which is why a show at any of Chicago’s top comedy clubs is always a good idea. Our favorite spots include Zanies and the Second City, where you can watch sketches, improv performances and stand-up routines from some of the best local talents.

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Jeffy Mai
Editor, Time Out Chicago
  • Things to do
  • Streeterville
  • price 2 of 4

Chicago is home to some of the tallest buildings in the world so why not take full advantage of them? Climb more than 1,000 feet above ground to CloudBar at 360 Chicago or the Signature Lounge and watch the sunset from the city’s highest points. Pair the stunning views with a cocktail to really enhance the experience.

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  • Attractions
  • Parks and gardens
  • East Garfield Park

Described as “landscape art under glass” when it opened in 1908, the conservatory, while being one of the largest in the world, also boasts revolutionary architecture. With the building’s haystack shape and walls of stratified stonework, landscape architect Jens Jensen considered the Fern Room in particular, with its “prairie waterfall”—a stone and water element within a glass structure—to be one of his greatest achievements. When winter rolls around, the 120,000 lush plants that populate the space make a great backdrop for a date. Sneak a kiss in the Desert House or stroll through the Aroid House hand in hand.

  • Bars
  • Cocktail bars
  • Uptown
  • price 2 of 4

Established in 1907, the Green Mill is a local institution for live jazz. This vintage cocktail lounge has a storied history—it was a favorite hangout of Al Capone—and has played host to notable acts like Billie Holiday and Von Freeman. There’s usually a line to get in but once you do, you’ll be treated to enthralling performances, mean martinis and a charming evening with your date.

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Jeffy Mai
Editor, Time Out Chicago
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  • Things to do

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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  • Things to do
  • Hyde Park

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.

  • Things to do
  • Lincoln Park

See some 1,200 animals, from apes to zebras, at the oldest and one of only a few free zoos left in the country. Locals know that the attraction is open all year, with ZooLights taking over in the winter months and events like Craft Brews at the Zoo offered in the summer. No matter the season, you and your date can see aardvarks, howler monkeys, polar bears and snakes.

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See the stars at the Adler Planetarium
  • Museums
  • Science and technology
  • Museum Campus
  • price 1 of 4

There's a reason so many Chicagoans take their engagement photos at this institution. Situated at the outermost point of the Museum Campus peninsula, the Adler boasts specular skyline views—arguably the best in the city. But the building itself ain't too shabby, either. Opened in 1930 as the first planetarium in North America, the Adler is a National Historic Landmark. Make it a date night at the museum's weekly event, Adler at Night.

  • Movie theaters
  • Independent
  • Wrigleyville

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. It's gorgeous, and regularly hosts director Q&A's as well as weekly midnight screenings of cult classics. Also, the concession stand here tops its popcorn with real butter.

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  • Hotels
  • Boutique hotels
  • Loop

Whether you're checking in for a romantic staycation or you're exploring the storied hotel's public-facing bars and restaurants, there's no shortage of charm at this luxury boutique property. Take in unparalleled city views from Cindy's rooftop, splurge on a special meal at Cherry Circle Room, face off in the Game Room or split an order of fries at Shake Shack—the possibilities are endless.

  • Things to do

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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  • Things to do
  • Literary events
  • Woodlawn

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.

  • Shopping
  • Liquor stores

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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  • Bars
  • Beer bars
  • Wicker Park
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Whether it's your first date or your 400th, Emporium Arcade Bar offers interactive fun to break up date-night monotony. Face off against your partner in Mortal Kombat, take turns playing Ms. Pac-Man or clean the table with a round of pool. As an added bonus, all Emporium locations allow guests to bring in outside food, so you can add dinner to the mix, too.

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  • Restaurants

Without a doubt, one of the most romantic things to do in Chicago is dining out for date night. But you can still replicate that experience at home while staying 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 dining destinations. Don't forget to toss in a bottle of wine to up the ante.

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