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 to 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 in one of the cozy, curtain-covered booths at Gejas Cafe.

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. Or soar above the city day or night on the new Navy Pier Centennial Wheel.


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 in the downtown area on summer weekends. But it's worth it. With the Chicago...  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


Chicago Botanic Garden


Get lost meandering through any of the Chicago Botanic Garden's 27 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




Geja's Café has topped Chicago's "Most Romantic Restaurant" lists for years. The fondue dining experience lets you cook your food at the table. Live classical and flamenco guitar add to the ambiance. Diners first walk down a few steps to enter...  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 music joint, open till 4 a.m. each night and 5 a.m. on Saturdays. Once a hangout of Al Capone, Charlie Chaplin and Gloria Swanson, the place has tons of character. The curvy bar...  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 McCormick Tribune Ice Rink. The downtown rink has a gorgeous backdrop of skyscrapers, which looks...  Read More


Navy Pier Centennial Wheel
Photo courtesy of Navy Pier


Opened in May 2016, the Navy Pier Centennial Wheel is a great place for a romantic ride. Located on Navy Pier, the entertainment venue that juts out into the lake, you'll get fantastic views of Chicago's skyline and lakefront. The wheel is 200...  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


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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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