What are the best things to do on a romantic trip in Chicago?

Answers from Our Experts (3)

When planning a romantic trip, Chicago provides the essentials — seclusion, culture, fine dining — and a lot more. Whether you bond over music an outdoor concert, take in some art or go on a cruise, you’ll have plenty of options. Here are our picks for the five best ways to romance someone, Chicago style:

1. Millennium Park. During the late spring and summer, Millennium Park hosts free music concerts every Monday featuring artists like Iron and Wine and Justin Townes Earle. Pack a picnic dinner and a blanket and head to the downtown park; romance ensues. Another great outdoor venue (though this one has a price tag) is nonprofit organization Ravinia, which is about 30 minutes north of the city and puts on up to 150 concerts from September to June. Unlike Millennium Park, you can bring wine to sip on while you listen to everything from classical musicians to Steely Dan.

2. Art Institute. The classic works at the Art Institute of Chicago and the eclectic pieces at the Museum of Contemporary Art are bound to stir a lot of stimulating conversation with your date. Top off a day spent perusing museums with a luxurious meal. Forbes Travel Guide Four-Star Sixteen in Trump International Hotel & Tower Chicago wows with a great view of the skyline and river out of its expansive windows.

3. Broadway in Chicago. The Broadway in Chicago production company has made a name for itself by bringing in big-ticket showstoppers like Mamma Mia!, Rent and, of course, Chicago. Most of the touring productions Broadway in Chicago brings in hit the stages of the Bank of America Theatre and Cadillac Palace Theatre. The Ford Center for the Performing Arts, Oriental Theatre housed Wicked since its Chicago debut in June 2005 until its closing in January 2009, making it the highest-grossing Broadway musical in Chicago to date. Any Broadway show in Chicago will make for a romantic night out with your special someone.

4. Willis Tower. From the observation deck at the 103rd floor of the Willis Tower, formerly the Sears Tower, you can see up to 40 miles out in either direction on a clear day. Take a picture of you and your date’s feet on one of four glass balconies 110 stories up called the Skydeck. The view is exhilarating, and will make you and your loved one feel closer amid such a big, bustling city.

5. Navy Pier. Depending on your mood, hop into one of Navy Pier’s many different kinds of boats. Take a relaxing ride on a larger Shoreline Sightseeing Boat or jump aboard a speedboat called Seadog — you’ll realize why Chicago is known for its architecture on both. Once your boat is docked, reach new heights on the 150-foot Ferris wheel. Plus, during the summer, it’s likely you’ll catch some fireworks while you’re up there.

Michael D. Solis

Looking for romance while in Chicago? We recommend going on a horse and carriage ride, taking a long walk along the lakefront, going ice skating (or picnicking) at Millennium Park, having dinner at the Signature Room in the Hancock Building or attending a play.

Lauren Viera

Presuming you’re visiting between April and October, you can’t go wrong with a sunset cruise along the Chicago River. Several tour companies offer themed cruises that make it possible to do just about anything while floating down river (brush up on Chicago history, learn about local breweries, etc), but my favorite line is Chicago’s First Lady, which partners with the Chicago Architecture Foundation for its docent-led Architecture River Cruise. Or, opt for a dinner cruise on Lake Michigan. Several charter cruise companies depart from Navy Pier in time to catch the sunset on the lake.

A lot of romance can be lent to a simple evening stroll in the park, and Chicago has a ton of beautiful settings. (Our 19th century nickname “City in a Garden” still rings true.) Downtown, Lurie Garden in Millennium Park is comprised of a maze of hedges, making for several private corners to sit a spell by the sculptural stream winding through it. In Lincoln Park, just north of downtown, the beautiful Alfred Caldwell Lily Pool incorporates prairie-school design into water sculptures, with swans swimming in the background.

Back in the city, one of the most romantic date spots for drinks and hors d'oeuvres or an intimate light meal is RM Champagne Salon in the West Loop, a short cab ride from downtown. Opened in 2012, the delicately French hideaway is tucked behind popular restaurant Nellcote, and its exposed brick, candlelit patio feels like provincial France.

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