Romantic Things to Do In Chicago

Chicago may not immediately appear to be a romantic city. It's big, loud, and busy. El trains clatter on the overhead tracks, taxis sit in traffic, and workers rush to and from offices and commuter trains. But amidst the hustle and bustle of the city, there are plenty of opportunities for romance. Here are some of the most romantic things to do in Chicago, updated for what's still open. Two of our original picks, the Signature Lounge and the carriage rides, are gone, and so are three of the restaurants.

A drink with the view, 94 floors up

For years our first pick was the Signature Lounge on the 96th floor of the John Hancock Center, where the price of a cocktail bought you the whole skyline, and you waited 20 minutes for a window table on a weekend night. The Signature Room and its lounge closed in September 2023, and the building now goes by its address, 875 North Michigan Avenue.

The replacement is two floors down. CloudBar is inside the 360 CHICAGO observation deck on the 94th floor, so you need a deck ticket to get in. The Sip & View ticket, from $44, includes one drink or snack, and the deck is open until 11pm with last entry at 10pm. Get there about an hour before sunset, share a drink as the sun goes down over the city, and stay while the skyline lights up.

If paying admission for a cocktail bothers you, Cindy's, on the 13th floor of the Chicago Athletic Association hotel at 12 S. Michigan Ave., looks straight over Millennium Park to the lake and costs nothing to walk into. It has a glass atrium, so it works in winter too. Our rooftop bars page has more.

What happened to the carriage rides

A little cheesy? Maybe. But cuddling in a horse-drawn carriage as it rolled past the lights of Michigan Avenue used to be on this list. You can't do it anymore. The city banned horse-drawn carriages starting January 1, 2021. The closest thing now is a slow walk up the Magnificent Mile after dark, when the stores are lit and the crowds have thinned, or a sunset cruise on the river. The Chicago Architecture Center river cruise runs from mid-March to late November, lasts 90 minutes and starts at $57. Book ahead for anything around sunset. Our ways to get out on the water page has other boats.

Dinner worth dressing up for

There's no shortage of romantic restaurants in Chicago, many of which can cost a week's salary. When we first wrote this, the big names were L2O, Tru, Alinea and Les Nomades. Only Alinea is left. L2O closed in 2014, Tru in 2017, and Les Nomades, the old-school French room in Streeterville, closed in October 2025 after 32 years.

Alinea, at 1723 N. Halsted St. in Lincoln Park, is still the most famous meal in the city, even after Michelin dropped it from three stars to two. Tickets are prepaid and bookings open about two months out, so plan ahead. Smyth in the West Loop is now the city's only three-star restaurant. Our Michelin-starred restaurants guide lists them all with how and when to book.

For something quieter, North Pond, 2610 N. Cannon Dr., sits inside Lincoln Park itself, next to the pond it's named for. It serves a six-course seasonal tasting menu at dinner, Thursday to Sunday, and a three-course brunch on Sundays. It held a Michelin star as recently as 2022. It's reservation only, and the dining room is small.

Luckily, there are some less-expensive options as well, thanks to Chicago's BYOB culture. Plenty of restaurants let you bring your own wine, sometimes for a corkage fee, which cuts the bill a lot. Many are informal, but a few pair serious cooking with your own bottle. The standouts are both on the Michelin list. Schwa, 1466 N. Ashland Ave., is Michael Carlson's BYOB tasting menu, open Wednesday to Saturday. EL Ideas, near 14th and Western, is also bring-your-own and is the lowest-priced starred tasting menu we could confirm. See our BYOB restaurants page for more.

A stroll along the lake or through Lincoln Park

Chicago has no shortage of beautiful skyline views. One of the most romantic spots to see the city from is along the Lakefront Trail. During early evening you'll be sharing the path with joggers, walkers and bikers, but once the sun sets it thins out, and the lights of the city's buildings shine in the distance. The stretch between Oak Street Beach and North Avenue Beach gives you the skyline down Lake Shore Drive. For a quieter spot, head south to Promontory Point in Hyde Park, a landfill peninsula near the Museum of Science and Industry where the locals sit on the limestone blocks and look back north at the city.

During the day and early evening, Lincoln Park is the perfect lover's retreat. Wander through the free Lincoln Park Zoo, open every day, stroll around North Pond before dinner there, shop for a picnic at the Green City Market (Wednesday and Saturday mornings in the warm months), and find a spot on the grass. Our picnic guide has ideas.

A warm room full of plants

In winter, when the lakefront is out of the question, go to the Garfield Park Conservatory, 300 N. Central Park Ave., one of the largest greenhouse conservatories in the country. Jens Jensen designed it, and it opened in 1907. It's right by the Conservatory stop on the Green Line. It's closed Mondays and Tuesdays, open until 8pm on Wednesdays and until 5pm the rest of the week, and adults from outside the city pay $10. Reserve ahead, since same-day entry isn't guaranteed. The Wednesday evening hours are the ones to aim for.

Spend a day at the museum

Chicago's many museums may be filled with kids and families on weekends, but on weekdays they're far quieter. Discuss the meaning of art or the love life of a famous painter and then steal kisses in empty exhibit halls. The Art Institute stays open until 8pm on Thursdays, which makes for a good date night, but it's closed Tuesdays and Wednesdays. On the Museum Campus, choose from the Shedd Aquarium, the Field Museum or the Adler Planetarium, at the tip of Northerly Island, where the skyline view from the front steps costs nothing. Farther south is the Griffin Museum of Science and Industry.

• More on Chicago museums

Listen to jazz

Chicago has a proud history of jazz and blues music, and there are plenty of venues with live music several nights a week. One of the most famous is the Green Mill, at 4802 N. Broadway in Uptown (not Andersonville, as we said the first time around). The Lawrence stop on the Red Line is a block away, about 20 minutes north of the Loop, and the Red Line runs all night.

City records put the Green Mill's opening in 1898, and in the 1920s one of Al Capone's men was part-owner. The current room dates to 1935, and Dave Jemilo has run it since 1986. The place practically drips with history, and both the performers and the audience clearly love the music. During sets the room goes quiet except for the music, and the staff will make sure it stays that way, so it's an ideal place for those who would rather cuddle than chat. It's cash only, with no reservations. The Green Mill website lists the schedule, and our blues and jazz clubs page has more rooms.

Planning around February 14? See Valentine's Day in Chicago.

Photos by jill d; digging90650; rebecca ann