The most romantic things to do in Chicago for couples

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.

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.

If you’ve ever been on the Chicago Riverwalk and thought “an open-air, hot-tub boat would really elevate this experience,” then Chicago Electric Boat Company has the perfect date night for you. Float down the Chicago River in style while cozily encapsulated in a floating hot tub boat. You’ll see views of downtown Chicago you’ve never seen before and set a new standard for date night. The boat’s are BYOB, so that extra bottle of wine could be the cherry on top of a perfect night.

Don't bring wine to the date—bring the date to the wine! Dive into the world of winemaking with guided tours at the Chicago Winery. Expert wine-enthusiasts go through the process of sourcing to bottling to final products. Grab a couple of the winery's on-site blends to bring even more sophistication to date night. Or book the winery's date night package for a tour, tasting and dinner at Liva.

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.

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.

At one of Chicago’s favorite beaches, that is. Grab a cup of coffee from one of Chicago's best coffee shops and head to arguably the most underrated romantic spot in the city: the shores of Lake Michigan. You don’t have to be a morning person to admire the city skyline at dawn—especially when the better view is your date. Sunsets and romance may go hand-in-hand, but what might be even more Lifetime-movie worthy? Watching the orange and pink hues flood the horizon as you listen to the sound of the lapping waves and soak up enough butterflies to kick start your day.

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.

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 and watch the sunset from the city’s highest points. Pair the stunning views with a cocktail to really enhance the experience.

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.

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.

Bored of your average sourdough baking class? Then look no further than Chicago's assortment of out-of-the-ordinary offerings. There are many benefits to learning a new skill as an adult, whether it’s for career advancement, making friends, meeting singles or simply being creative—and the nicher the class, the more memorable. The city’s top libraries, museums, art studios and other cultural institutions feature class topics ranging from our cultural obsession of Mars to daring rodeo tricks. So swallow your fear of heights and grab your tarot deck for an unforgettable night out.

Want to see if you and your date have the same decorating tastes? Spend an evening strolling through some of Chicago’s favorite art museums and galleries. Extended evening hours at the Art Institute of Chicago are perfect for an after-work date—explore the majestic 1890s-era building and its massive collections—or check out other places like the National Museum of Puerto Rican Arts and Culture, National Museum of Mexican Art, Ukrainian Institute for Modern Art and Museum of Contemporary Art for an educational showcase of the best Chicago art. Plus, given their locations near bars and restaurants, they're easy segues into an evening of debriefing over craft cocktails.

If literature is your love language, there’s nothing more romantic than bonding over books with your date in a cozy setting. Uncover the layers of your date’s soul by browsing the shelves at Chicago’s best bookstores, strolling historic Chicago Public Library branches (including sneaky kisses as you get lost in the stacks) or dissecting their reading list over cocktails at Lincoln Park's literary-themed speakeasy The Gatsby. Swapping and comparing shared literary interests—whether fiction, nonfiction, poetry or essays—creates both natural conversation starters and deeper connection.

Revel in the sweet sounds of the Chicago Symphony Orchestra with that special someone. Even if classical music might not be your thing, the Symphony often features diverse experiences like jazz musicians and immersive fashion shows. The sight of the Orchestra accompanied by world-class quartets and string musicians are sure to ooze romance.

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.

Everyone hopes for a magical ending to a date, and perhaps the best way of making that happen is with a show at the Chicago Magic Lounge. Guests enter through a faux laundromat before sitting down to spellbinding tricks that’ll leave them oohing and aahing. And for a nightcap, head to the Performance Bar to enjoy a variety of craft cocktails.

Drive-in theaters are a dying breed, but there are still a few places in and near the city for an old-school moviegoing experience. Catch the latest blockbuster or a cult classic with your date in a more private setting—your vehicle. It sure beats sitting in a crowded movie theater surrounded by strangers.

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.

See some 1,100 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.

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.

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.

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.

While you’re waiting for any of the many offerings at the Chicago Athletic Association, take a load off at the Drawing Room on the second floor lobby. The open space transports you to a centennial library, sporting wall-length wooden bookshelves and homey fireplaces. Sip on your favorite drink, snack on a meal and maybe crack open a book with your special someone to soak in the vibes.

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.

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.

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.

Best suited for the warmer months, a picnic in one of Chicago's beautiful parks is the perfect romantic activity for couples. Pack a meal, or grab something from a restaurant, and head over to a green space for a wonderful date. In the summertime, parks are also home to free music fests and film screenings, as well as the finest views in Chicago.

Gym rats argue there’s nothing like the “sweat bond,” the special emotional connection one gets from working out together. So if it works for them, why not test it out on a burgeoning relationship? Possible pit stains may not seem like the most conventional romantic outing, but there’s no denying there’s something sultry about watching muscles flex and sneaking side eyes through shared misery. Flirt through a partner yoga class—with lots of laughs at failed acrobatics, surely—or head to one of Chicago’s best gyms, like Ethos, for strength workout topped off with a post-sweat sauna and cold therapy session.

For most locals, Navy Pier can feel like a tourist trap, but there's no denying the romantic appeal of a 200-foot-tall Ferris wheel with bird's-eye views of the city skyline and Lake Michigan. The gondolas are enclosed and climate-controlled, so you don't have to worry about freezing, and each ride lasts about 15 minutes, giving you just enough time to cuddle up with your partner.

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.

Nothing says romance quite like a box of chocolates. If you want to do something sweet for your S.O., swing by one of the best chocolate or candy shops in town to pick up an array of sugary confections to enjoy at home.

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.

Checked all of the above off your bucket list? Then plan a romantic escape to a nearby destination. The adventurous can spend the day hiking, skiing or boating while those looking for relaxation can visit a museum or winery. Either way, you should book a hotel so you can relax by soaking in a hot tub or curling up by the fireplace after a full day.