The Hoxton has four options for rooms (Snug, Cosy, Cosy Up, and Roomy). None are palatial in size (the largest rooms are 300 square feet), but all are modern and stylish, with leather headboards, brass lighting, and retro-styled speakers.
Visited by Joseph Hernandez
Courtesy of the Publishing House
This 11-room, three-story property located in the former Historic Free Methodist Publishing House is private and low-key while still being in the center of it all in the West Loop. While the space is now a bed and breakfast, it has lived many lives—as the Walter Rudolph Casket Factory in the 1930s through 1950s and the Museum of Holography from 1976 to 2009. You can feel that historic charm in its current iteration, even after the hotel’s renovation in 2016. There’s original wood paneling and maple flooring, but the property now feels updated to suit a modern day traveler.
Design varies with each room, which are named after Chicago literary figures, and the communal third-floor living room, meant for lingering, has a grand piano and double-sided fireplace. There’s also a wine bar, the Press Room, in the basement. Because of the property’s intimate size, it’s a great option for a buyout so a big group or wedding party can all stay together.
Visited by Joseph Hernandez
Down by the River
The Loop and River North are bustling business and tourist areas. You can access most CTA rail lines (including the Blue Line, which runs to the airport) and walk to iconic landmarks like Millennium Park and the “Bean,” the Art Institute of Chicago, and the Riverwalk. Of course, you’ll need to eat when you’re checking landmarks off your to-see list.
Walk in at Gus’ Sip & Dip (a BA Best New Bar of 2025) for no-fuss classic cocktails and a Wagyu beef dip in a tavern setting, or delight in Indian fine dining at Indienne (a Best New Restaurant of 2023). You can’t miss a daytime stop at Doma, a Croatian café with a dynamite breakfast sandwich and destination-worthy hashbrowns. Plus, River North is home to many Chicago classics like Rick Bayless’s Topolobampo and Shaw’s Crab House. We recommend a quick trip south to Chinatown for an MSG martini and neon-drenched vibes at Nine Bar.
Courtesy of the Chicago Athletic Association
The Chicago Athletic Association offers an elevated members club experience without the steely pretension. It’s also one of the most gorgeous properties in town. The common spaces in this Venetian Gothic building include a game room and a historic basketball court (a holdover from the property’s previous life as an actual athletic club). As for dining, Cindy’s Rooftop offers cocktails with unbeatable views of Millennium Park on a year-round terrace that’s enclosed by a photo-worthy glass atrium, and the cozy Drawing Room in the 19th-century-inspired lobby has all-day fare in a space you wish were your living room. The hotel also just debuted Midosuji, an eight-seat omakase counter with two seatings a night.
