The 6 Most Romantic Hotels in Chicago

It's easy to be seduced by the bones of the Chicago Athletic Association: the 1890s Venetian Gothic tower operated as a private club back in its heyday. A masterful revamp from the minds behind the Ace Hotels has given it new pizzaz—we're talking vintage chandeliers, stained glass windows, 19th-century wood fireplaces, and a fresh shine on the original mosaic-tile floors, which extend into the Game Room (where shuffleboard, bocce, and billiards await twosomes looking for some friendly competition). After cozying up to views and bites at Cindy's, the rooftop restaurant lit by curved skylights, grab one of the hotel's tandem bicycles for a spin around town.

The historic Peninsula, smack dab on Magnificent Mile, was already beautiful—but a recent $37 million overhaul made it that much better. In addition to a new bi-level spa and 19th-floor swimming pool, there are fresh nods to its Asian-inspired roots, including the big-on-style Shanghai Terrace restaurant that channels 1930s China. Rooms are some of the most spacious retreats in the city (you'll want to spend lots of time testing out the king-size bed and deep soaking tub) but the lobby is our favorite hangout thanks to its gold ceiling frescoes and daily afternoon tea...not to mention a mean Sunday brunch. Looking to bop around the neighborhood? The hotel's BMW is on hand to chauffeur you.

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Soho House, the first boutique to hit Chicago’s West Loop, has become the "it" spot where Chicagoans and visitors come to see and be seen. And you'll want to hang around—there's more than enough here to occupy you and your beau for multiple afternoons, including a club lounge with its own Ping-Pong table and piano, a movie screening room, a spa, and—the pièce de résistance—a 60-foot rooftop pool and bar-slash-bistro with views of the skyline. Of course, guest rooms are nothing but stylish, with English club chairs, rotary phones, and exposed concrete and brick left over from the original 1907 warehouse.

In Chicago, it doesn't get much more intimate than this 11-room boutique, which takes its former life as a publishing house (as you might have guessed) to heart. Individually designed guest rooms are eclectic, full of art, and named after an author, book title, or character in a book about Chicago—including Audrey Niffenegger (who wrote The Time Traveler's Wife) and Upton Sinclair, who based The Jungle on a neighborhood close by. In the common area, guests can sit down for breakfast at the communal table or cozy up in one of the leather chairs by the fireplace with something from the book rack. If you'd rather keep things more private, the 70-seat Press Room basement wine bar and restaurant might be more to your taste.

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That this 60-story stunner in Chicago's Gold Coast neighborhood was modeled after a 1920s Parisian grand dame tells you all you need to know about the kind of romance you'll find here. (No wonder so many weddings are booked here year-round.) Talk about an entrance: cars pull up a brick-paved driveway and deposit guests at the entry of the chandelier-lit, velvet-couch-lined white marble lobby. Upstairs, guest rooms are even more glamorous—think pops of platinum and gold, furnished terraces, black granite fireplaces‚ and huge soaking tubs—as is the spa, where you can indulge in a lava-shell massage. When you're feeling peckish, stop by Margeaux Brasserie, the Parisian café-like restaurant helmed by James Beard Award-winning chef Michael Mina, which hosts a weekend jazz brunch on Saturdays and Sundays.

The 1923 neoclassical London Guarantee Building reopened as the 452-room LondonHouse hotel in 2016 with a glamorous new glass tower overlooking the Chicago River. The restoration was impressive, full of subtle details like jazz-themed motifs that pay homage to the building's former life as a 50s music club and custom artwork and monogrammed duvets in guest rooms. Not so subtle is the gold-leaf ceiling in the rotunda or LH, the city’s first tri-level rooftop bar that serves retro cocktails and small plates against a backdrop of skyscrapers. Looking to seal the deal? Ask for a river view room on a high floor for a show-stopping stay.