Let love rule: Romantic things to do in Chicago

Romance is always in the air in Chicago and if you want to take that special someone on a date, there are endless possibilities of things you can do.

If the weather's cooperating, nothing beats a scenic stroll hand-in-hand, either through the gorgeous Chicago Botanic Garden or along the city's beautiful lakefront path, with the skyline behind you. Afterward, grab a glass of bubbly and listen to live music at Pops for Champagne, or cozy up in a booth and eat chocolate fondue at Gejas Cafe.

If you both love to learn new things, book a tour. The Chicago Architecture Foundation River Cruise is popular among locals and visitors alike because you not only get to learn more about the city but you’re traveling on a boat along the calm Chicago River.

There is no shortage of entertainment options in Chicago, ranging from live music to comedy clubs and live theater performances. The Green Mill Cocktail Lounge features live jazz almost every night while improv actors keep fans laughing all the way home after a performance at The Second City.

Another option is to get naked. At a spa, of course. Check out Allyu Spa where you and your loved one can get a couples massage in one of the most relaxing places in the city.

Chicago Architecture Foundation River Cruise
Photo courtesy of Photo courtesy of Choose Chicago

Seeing Chicago's architectural beauty from the decks of a river cruiser is a must for both locals and visitors. One of the city's most unique tours, the CAF River Cruise takes visitors along the north and south shores of the lake. Guests will...  Read More

Chicago Lakefront Trail
Photo courtesy of Photo by Jamie Bartosch

Walk, job, bike, roller blade ... no matter how you travel along this 18.5-mile lakefront path, it's going to be beautiful. It's also going to be congested, especially downtown on summer weekends. But it's worth it. With the Chicago skyline on...  Read More

Geja's Café is not a place where you sit back and be served. It's a fondue dining experience which means you'll be cooking your food at your table. Live classical and flamenco guitar add to the ambiance. Diners first walk down a few steps to...  Read More

Drake Hotel Palm Court Traditional Afternoon Tea
Photo courtesy of Photo courtesy of Drake Hotel

A live harpist often performs during the elegant afternoon tea in this historic Chicago hotel - a tradition here for nearly a century. Held in the gorgeous Palm Court room, with a fountain in the center and an enormous chandelier, you feel like...  Read More

Many spas offer a relaxing environment but few make the experience as calming and relaxing as Allyu Spa. The space pays homage to Mother Earth. Guests will find many natural elements throughout the space from reclaimed barnwood, walls of...  Read More

Chicago Botanic Garden

Get lost meandering through any of the Chicago Botanic Garden's 26 gardens and four natural areas that sit within nearly 400 acres of land and around nine islands. Located in a suburb about 25 miles north of Chicago, the gardens are well worth...  Read More

Second City
Photo courtesy of Photo courtesy of Choose Chicago

The couple that laughs together, stays together. So take your special someone to see the world's premier comedy troupe, The Second City. The improv comedy club has launched some of the biggest names in the business, including John Belushi, Dan...  Read More

Green Mill Cocktail Lounge
Photo courtesy of Photo courtesy of Choose Chicago

Trendy folks and jazz aficionados regularly flock to this cool joint. Once a hangout of Al Capone, Charlie Chaplin and Gloria Swanson, the place has tons of character. The curvy bar still looks like a speakeasy, setting the scene appropriately...  Read More

Ice skating at Millennium Park
Photo courtesy of Photo courtesy of Choose Chicago

So many rom-com movies have ice rink scenes where couples fall in love. Perhaps your love story can take place here at Millennium Park's ice rink. The downtown rink has a gorgeous backdrop of skyscrapers, which looks particularly beautiful at...  Read More

Chicago Helicopter Experience - CHE
Photo courtesy of Photo courtesy of CHE

For a romantic and memorable night in Chicago, take a helicopter tour of the city with Chicago Helicopter Experience, also known as CHE. The hour-long experience, of which about 20 minutes is up in the air, can be done day or night. The flight...  Read More


Meet Jamie Bartosch

Jamie Bartosch is a lifelong Chicagoan who thinks her hometown is the greatest city in the world. She is an award-winning newspaper reporter, a freelance travel writer, and the mother of two great kids.

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