Chicago Athletic Association Hotel
CHICAGO
Chicago’s Boutique Hotels: 12 Unique Places That Capture Windy City Vibes
By Jamie Dutton | June 17, 2025
AUTHOR BIO: With family spread across the Midwest and a job that has her in airports regularly, Jamie Dutton finds herself across the center of the U.S. regularly. She’s partial to BPTs and a Bell's Lager.
Back when I first started coming to Chicago, I’d crash on the futon of a college friend who lived off the Blue Line.
The couch had that signature IKEA bend in the middle and usually smelled faintly of Bernese mountain dog, because during the day it was, in fact, the favorite resting spot of a dog named Fred.
These days, I visit on the dime of my day job, which means no more shared showers or digging through drawers for a clean towel. Now I stay in hotels—different ones each time—so I can get a feel for new neighborhoods, eat my way through whichever restaurants are buzzing that week, and figure out which corners of this city still feel like they’re shifting underfoot.
This list is what I’d send to someone who asked where to stay in Chicago and actually wanted a good answer. Real boutique hotels—ranked by what you get, what you don’t, and where they drop you into the glorious Chicago sprawl.
1. Chicago Athletic Association Hotel
$$$$$ | MAP | WEBSITE | INSTAGRAM
I stayed here once on a press rate and regretted not paying full. The Venetian Gothic former men’s club from 1893 still owns the block on Michigan Avenue—game room, fireplaces, leather club chairs included. Rooms are dark and cozy, and yes, there are real fireplaces in some. You’re two steps from Millennium Park with multiple spots to grab a drink or bite inside.
3. Nobu Hotel Chicago
$$$$$ | MAP | WEBSITE | INSTAGRAM
On the corner of Randolph and Peoria, Nobu’s 115-room, Japanese‑minimalist take on industrial chic nails West Loop energy. The spa includes a 40‑ft pool and sauna, and the rooftop bar has real view power. Just don’t expect breakfast included—grab from Nobu restaurant or rooftop small plates.
4. Soho House Chicago
$$$$$ | MAP | WEBSITE | INSTAGRAM
This is where you stay if you want to pretend you live in a private club where everyone has great skin and a book deal. Housed in a 1908 industrial building in Fulton Market, Soho House is part hotel, part coworking space, part rooftop playground, and all very much aware of how good it looks in photos. The rooms feel like they were designed by someone who’s allergic to minimalism—velvet, wood, rugs on rugs—but somehow it not only works but will become the background of your new LinkedIn profile. As a guest, you get temporary access to everything: the 80-foot rooftop pool, the screening room, the gym, the spa, and whatever version of clubby creative energy is brewing that night at Fox Bar or Cecconi’s.
5. The Emily Hotel
$$$$$ | MAP | WEBSITE | INSTAGRAM
The 159 minimalist rooms feel fresh—modern, and Bauhaus‑inspired, with clean lines and local artwork. It doesn’t feel posh, but it doesn’t cheap out either. It’s a perfect home base for a West Loop itinerary, especially a girls’ weekend of ladies who are both ready to party and enjoy comfy beds.
6. 21c Museum Hotel
$$$$$ | MAP | WEBSITE | INSTAGRAM
Once a 1927 Tudor Revival building, now 297 rooms built around 10,000 sq ft of contemporary art space. You walk through gallery pieces on your way to the gym or a nightcap—that’s intentional. Around the Magnificent Mile, so you're close but not smack in the tourist sweep. It feels like a museum that lets you sleep in it.
7. Virgin Hotels Chicago
$$$$$ | MAP | WEBSITE | INSTAGRAM
Virgin grabbed the 1928 Old Dearborn Bank building, restored it with cathedral ceilings, terra cotta exterior—and no resort fees. There’s 250 rooms, two penthouses, plus three restaurants and a rooftop bar called Cerise. The app‑controlled room temp and minibar pricing (street-level, not markup) shows they flipped the script. Walking distance to Millennium Park and the theatre district—no hidden charges, no surprises.
8. Silversmith Hotel
$$$$$ | MAP | WEBSITE | INSTAGRAM
The Silversmith was built in 1897 as part of Jewelers Row and is now a 144-room boutique hotel with loft‑style rooms and 12-foot ceilings. The marble‑accented lobby and on-site New American restaurant make it feel polished without being gaudy. Just a block from Millennium Park and Magnificent Mile, this is the spot for people like me who want to see Chicago by foot. It’s also a solid choice if you want old‑school architecture with modern ease.
9. The Guesthouse Hotel
$$$$$ | MAP | WEBSITE | INSTAGRAM
The Guesthouse took a set of condo‑grade units and turned them into 25 spacious hotel suites—this place feels like someone’s well‑styled home. Many rooms have kitchens, washers, balconies, even BBQ grills—which is rare in the city . It’s dog‑friendly and has a far more local vibe than many Loop hotels. It’s ideal if you want apartment comfort and neighborhood character.
10. Hotel Zachary
$$$$$ | MAP | WEBSITE | INSTAGRAM
Right across from Wrigley Field, Hotel Zachary was built to honor the stadium's architect and heritage. You walk in and immediately feel the baseball-home vibe—portrait-lined halls, rooftop terrace ready for game days. The two-story lobby with a library-style bar is a solid pre-game hangout. If you’re in town for the Cubs or just want North Side energy, this hits.
11. The Hoxton
$$$$$ | MAP | WEBSITE | INSTAGRAM
The Hoxton is the kind of hotel where the lobby always smells like someone just opened a cedar wardrobe while brewing espresso, which is to say: it smells glorious. The rooms are small but smart, with vintage-style radios, hardwood floors, and blackout shades that actually block light. Downstairs you’ve got Cira, a Mediterranean spot that draws a steady crowd, and upstairs there’s a rooftop bar with skyline views and people pretending it’s not 43 degrees out. The location drops you right in the middle of Fulton Market, so you can walk to a dozen great restaurants without ever calling an Uber.
12. Kimpton Gray Hotel
$$$$$ | MAP | WEBSITE | INSTAGRAM
The Kimpton Gray feels like the hotel version of someone who wears cufflinks unironically. It’s set in a 19th-century insurance building with bones to prove it: marble everything, high ceilings, and a lobby bar that looks like a law library, complete with leather-bound casebooks and dark liquor on dark shelves. Rooms lean masculine and mid-century, with gray-on-gray tones and just enough baby blue to keep things from going full charcoal suit. Boleo, the rooftop bar under a retractable glass ceiling, turns out solid South American cocktails and a view that feels like a reward for surviving your meetings.
