Lofty steel factories and Prohibition-era speakeasies have been transformed into unique places to stay in the Windy City. Tucked between towering skyscrapers and historic stadiums, you’ll find boutique boltholes making names for themselves with retro designs, themed decor and crowd-beckoning bars. If you like a bit of flair and fun, check out these brilliant boutique hotels in Chicago.
The Robey sits on Wicker Park’s most coveted intersection, surrounded by vintage shops and small cafés. Built in 1929, the hotel’s prism-shaped Art Deco structure is home to minimalist ’50s-style rooms drenched in natural light. Choose between the Tower Rooms with terrazzo tiles and motorized blackout blinds, or the exposed concrete of the Annex Lofts, which inhabit a warehouse conversion. Venture up to the Cabana Club on the rooftop for far-reaching views of the city skyline and fresh morning dips in the triangular pool.
FOUND Hotel Chicago resides behind the cast-iron facade of the original Olympia Building, a Gothic shell containing stripped-back rooms. If you’re sticking to a budget, you can opt for the shared dorms with bunk beds, but if you’re looking for solitude, the private rooms all come with en-suite bathrooms. Whip up a home-cooked meal in the communal kitchen – or tear into steaks at Mason House – before heading to the karaoke bar to sing your heart out and get ready for a night out in the cosmopolitan River North neighborhood.
Take a step into the IVY Hotel to find a sleek space lined with smoky contemporary art and atmospheric neon-violet lighting. Watch the world go by while sipping on a signature pumpkin spice martini at the marbled lobby bar, or head up to the roof to take in views of the city’s cloud-brushing architecture over charcuterie boards. Downstairs, you’ll find roomy suites with fuschia furniture, platform beds and deep tubs, inviting you to sprawl and soak to your heart’s content.
FieldHouse Jones is a blast from the sporting past. An artsy tangle of vintage tennis rackets hangs in the DropShot Coffee & Snack Bar, looking as if they have been blown in by the famous breeze of the Windy City. Meanwhile, hidden behind an “Employees Only” door and cluster of mops is the aptly named speakeasy Janitor’s Closet. There are shared single-sex dorms for the budget-conscious or private rooms with gym-locker-style cupboards and eco-friendly toiletries. Tucked in the basement is also a games room, complete with classic gems such as air hockey, foosball and a giant slot-car track.
SOPHY Hyde Park is a gallery-style hotel brimming with kaleidoscopic art, vintage posters and geometric light fixtures. Its community-focused ethos shines throughout. The array of art found in the on-site restaurant, Mesler Kitchen, comes from the students of Hyde Park Academy High School, while local artist Joey Korom is responsible for the abstract murals brightening each room. When you’re not tucking into chicken and sugar waffles among the literature-stacked shelves of the restaurant, you should indulge in a caffeine-fueled cocktail on the outdoor patio.
A passion for fitness lies at the heart of the Hotel at Midtown – its gym-with-rooms approach is a haven for exercise enthusiasts. Rooms with tobacco-leather furnishings and killer views of the skyline also come with honorary membership at the Midtown Athletic Club. Get your endorphin fix from the indoor tennis courts, cycle studio, Olympic-length pool or boxing gym, and then treat yourself to CBD treatments and skin-awakening facials at the Spa at Midtown. On your doorstep are also the foodie haunts and vintage boutiques of trendy Bucktown.
A stone’s throw from the famous Wrigley Field, the Wheelhouse Hotel is infused with baseball-themed nostalgia. A swarm-like collection of hanging baseball bats and a vintage scoreboard decorate the lobby, while elsewhere, you’ll find memorabilia such as classic stadium seating and retro hotdog ads. Rooms are less on the nose – a sophisticated mix of exposed brick, floor-to-ceiling windows and oceanic blues. The minibars are stuffed with local snacks, and the famous Wrigley’s gum will be sitting on your pillow on arrival. However, for something heartier, check out nearby eateries such as Lucky’s Sandwich Company or Cozy Noodles & Rice.
The Majestic Hotel nods to Wrigleyville’s past with leather tub chairs, vintage Chicago Cubs memorabilia and black-and-white baseball photography. Dressed in abstract art and golden accents, rooms range from standard queens to the Sunroom Suite – its kitchenette and sitting room are ideal for families or extended stays. While amenities are minimal, you’ll receive a complimentary pass to a nearby fitness club, and there are cookies in the lounge every afternoon. You are also a short stroll from the famous Wrigley Field and Clark Street’s popular pubs and clubs.
Hotel guests at this members-only creative club have access to exclusive bars, restaurants and a rooftop pool, amenities all coveted by the average Chicagoan. The six-story building in the West Loop has 40 rooms in an industrial space commissioned by an art collector in 1907. Its features include Neoclassical tiles at the front entrance and a gym with genuine-leather boxing equipment.
