With their breezy rooftop bars, edgy designs, and hotter-than-hot restaurants, these six boutique hotels—all under 100 rooms—are . Time to check in.
An iconic 1929 Art Deco office building in Wicker Park has become the neighborhood’s buzziest new hotel. Following a three-year revamp, restored details like the marble and brass lobby and rooftop spire pair perfectly with the fresh minimalist aesthetic—all 69 rooms come with hardwood floors, mid-century modern furniture, and floor-to-ceiling windows that overlook Wicker Park’s defining six-corner intersection. The ground-floor French bistro is another way to take in the neighborhood, as is the sophisticated rooftop bar, the Cabana Club, where guests sip mojitos and margs while soaking in the skyline views.
Soho House Chicago
It’s a see-and-be-seen kind of atmosphere at Soho House, the first boutique to hit Chicago’s West Loop that’s fast become the spot to hang. Once you check in, you’ll have access to lots of members-only perks, including the fifth-floor club lounge (complete with a grand piano and Ping-Pong tables), screening room, spa, and 60-foot rooftop pool and adjacent open-air bistro and bar, where Chicago’s style set come to sip stiff drinks alongside views of the John Hancock and Willis towers. Downstairs, the 40 industrial-chic rooms pay homage to their retro warehouse digs with exposed brick and concrete, English club chairs, and rotary phones.
A more perfect name could not exist for the Guesthouse Hotel, whose 25 one-, two-, and three-bedroom apartments (formerly part of a condo complex) each feel like the guesthouse of your closest family friend. There’s charm at every corner, from the pale gray walls and wooden floors to the striped throw pillows and leather couches, as well as all the amenities you’d want to feel truly settled—we’re talking good-sized living rooms, eat-in kitchens, washer/dryers, a balcony with a grill, and free WiFi for ordering in (Southport Grocery can deliver breakfast and lunch, while Calo is everyone’s favorite local pizza joint).
Longman and Eagle
Night owls rejoiced when, in 2011, one of Chicago’s hottest restaurants decided to open an inn upstairs. Just six rooms are decked out in gorgeous vintage, eclectic finds like curated minibars, original art, indie mags, and cassette players—details that might just help distract from the noise emanating from downstairs. Of course, the reason you’re here is to crash after a long and fruitful night at the namesake gastropub, which earned a Michelin star for its elevated American classics—beef tartare; fried chicken roulade—and impressive 150-varieties-strong whiskey selection.
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A strong community vibe surrounds FieldHouse Jones, a former dairy warehouse turned hostel-hotel hybrid in River North. There are communal dorms and a clutch of Airbnb-esque rentable penthouses in addition to private rooms, while the lounge areas—including a speakeasy, a coffee and snack bar, and an arcade room stocked with air hockey and Ping Pong tables—encourage mingling. Despite how “backpacker” it might sound, you’ll also find your fair share of families, couples, and suits passing through on business, who come for FieldHouse’s unique design (dartboard wall art; vintage trophies; local artwork) and affordable price tag.
For a chilled-out getaway in the heart of the Windy City, you can’t do much better than the Ivy, which sits on a tree-lined street just blocks from the lake. Don't let the hotel’s slim exterior fool you, inside 63 spacious rooms are spread out over 15 floors and refreshingly simple—no to mention eco-friendly—with their mahogany bamboo floors, sisal rugs, deep soaking tubs, and cool color palette of grays and purples. The place to be during the day or night is the rooftop bar, where light bites and drinks are served up with skyline views. FYI: There’s no pool or gym onsite, but daily passes to the River East Club are provided.