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The most romantic places in Chicago

Chicago's chilly weather makes for warm hearts

One of the most scenic spots in Chicago is Buckingham Fountain.

Believe it, Chicago is a city of romance. And possibly even more so for all the amorous pleasantries that go unseen during our brutal winters, in sweatpants, under blankets in our heated living rooms with a movie on TV. You know, the unsexy kind of stuff so often portrayed on Midwestern sitcoms.

When the weather permits though, we’re out and about like it's nobody's business, which makes Chicago one of the best cities for singles. Whether it's frequenting the nearest watering hole or lazing about Chicago's beaches, there's no shortage of things to do during Chicago's summer months, and a good portion of those places to go and sights to see are loaded with romantic potential. 

If you're looking for venues with the best opportunities to make sparks fly or rekindle an old flame, search no further. These are the most romantic spots in Chicago.

Chicago's most romantic spots


Buckingham Fountain

With its four Art Deco-style seahorses, Georgia pink marble and light and music show, this fountain built in 1927 is a sight to behold. From April through mid-October (depending on weather), 20-minute shows every hour on the hour feature 14,000 gallons of water spouting from 133 jets. In summer, see the nighttime colored light shows, capped off with a center jet shooting 150 feet of water in the air.

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Grant Park

Promontory Point

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.

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Hyde Park

Garfield Park Conservatory

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. About 120,000 plants representing some 600 species occupy the conservatory’s 1.6 acres, and flower shows happen four times a year.

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East Garfield Park

Chicago Athletic Association

To say the Chicago Athletic Association is beautiful is to put it mildly. Stay in one of the 241 luxury, boutique rooms—throwbacks to the club rooms of athletic associations long gone. From the unparalleled view of Millennium Park and Lake Michigan at Cindy’s rooftop restaurant to more great food and drink at Cherry Circle Room and Shake Shack, there’s no shortage of options.

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Signature Room

The Signature Room on the 95th floor of the John Hancock Center offers unparalleled panoramic views of Chicago for a dining experience wholly unlike any other. The view at night is beyond gorgeous, it's absolutely stunning. The food isn't half bad to boot.

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Alfred Caldwell Lily Pool

This semihidden oasis inside Lincoln Park, accessible from April to November, has become a popular spot for small weddings since it was restored and reopened in 2002. But you don't have to be getting hitched to feel the spot's naturally romantic vibe.

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Lincoln Park

Maggie Daley Park Skating Ribbon

If you don't mind the presence of kids, ice skating through the winding skating ribbon is a great way to spend a winter afternoon date; both the path and the skyline views make this far more enticing than your average rink.

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Millennium Park

Chicago Theatre

The Loop’s 5,000-seat Chicago Theatre was the opulent French baroque-style flagship of the Balaban and Katz movie palace chain when it opened in 1921. It’s still a beautiful venue (you’ve probably seen the famous illuminated Chicago marquee even if you’re from out of town) that’s surprisingly cozy for its large size.

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Harold Washington Library Center Winter Garden

The ninth floor of the Harold Washington Library Center is one of the unsung gems of Chicago. In what is otherwise a labyrinthian network of hallways and books reminiscent of Chicago's iconic bureaucracy, on the library's topmost floor is the Winter Garden, perfect for a couple to share a reprieve of peaceful quietude immersed in literature and fantastic surroundings.

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Langham Hotel

Opened in 2013 and occupying 13 floors of AMA Plaza (formerly the IBM Building), the Langham is the only hotel in the world to be found in a Mies Van Der Rohe building. The lushly appointed rooms are in contrast to the stark black slab of the exterior. Rated the nation's top hotel in a TripAdvisor survey less than two years after opening, the Langham is a pricey (rooms start at $395 a night) but inarguably luxurious place to spend a vacation or staycation.

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River North

The Green Mill

Al Capone and other gangsters used to hang here in the 1920s, but these days it’s all about the music. Owner Dave Jemilo, who returned the club to its original luster in the 1980s, books smart bebop and free jazz with a discriminating ear.

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