21 E. Bellevue Pl., Gold Coast
This boutique hotel feels at once like an urban loft and a cozy cabin, combining rich colors and exposed brick with stellar views of Lake Michigan and the Chicago skyline. Its Gold Coast location means it's just a walk away from shopping and dining on the Magnificent Mile (and legendary pizza from Lou Malnati's), though the admired Osteria Nico downstairs means you don't even have to leave the hotel for Italian with a view. Just as enticing are the modern rooms themselves, featuring velvet seating and Brooklyn-made D.S. & Durga toiletries. If you do decide to change out of the insanely comfortable robes and venture outdoors, though, take advantage of the hotel's complimentary offsite car service.
Ace Hotel Chicago
311 N. Morgan St., West Loop
In Chicago's buzzy and rapidly gentrifying West Loop, Ace Hotel has set up shop right across from Google's Midwest HQ. Fittingly, the 159-room property is a nod to the city's strong architectural history having partnered with LA-based Commune design studio to thoughtfully marry both utility and craftsmanship. Taking inspiration from Mies Van der Rohe and Frank Lloyd Wright, the hotel expertly mixes warm woods, clean lines, and rich textures. Commune and Ace also tapped Chicago's Volume Gallery, which specializes in American Craft, to collaborate on a series of pieces specifically for the hotel by emerging and mid-career area artists. In the guest rooms, the low-slung plywood furniture references Mid-century design with pops of blue, greens, and grays and geometric patterns. (One of our favorite rooms is the Loft, a 545-plus square foot space, where a turntable and selection of curated vinyl and an acoustic Martin guitar are also on offer.) Downstairs, Stumptown Coffee set up shop just off the lobby —it's their first location in the Midwest—making for an ideal pit stop before you explore the neighborhood by foot.
2018 W. North Ave., Wicker Park
The building itself is an art deco jewel that preserves much of the charm of its 1920s design, and its triangular footprint means each of the hotel's 69 rooms are filled with plenty of light.
19 E. Ohio St., River North
The second Freehand outpost (the first is in Miami) refers to itself as a hotel-slash-hostel, meaning they've made their beautifully appointed shared and private rooms exceptionally tourist and wallet-friendly.
The James (Closed)
55 E. Ontario St., Magnificent Mile
Simply put, this downtown hotel's proximity to some of the city's best sites can't be beat: Millennium Park, The Museum of Contemporary Art, and Michigan Avenue are all just steps away. It offers all the comforts and amenities you'd need (bike rentals, a great gym), in addition to a sleek, modern design that makes it nothing short of a city oasis.
505 N. State St., River North
Located in the hub of the art and design district, the Palomar is a modern, pet-friendly, eco-friendly, organic-oriented hotel that caters to active city visitors. The hotel organizes fun group exercise classes that include guided runs along Lake Michigan and ballet barre workouts on the hotel’s sundeck. Other novel perks are the in-room massages and yoga sessions. And, if you travel with your pets, you’ll be pleased with all the amenities that they’ll enjoy. Sable, one of the best bars around, is just down the stairs.
The Peninsula Chicago
108 E. Superior St., Magnificent Mile
We don’t say this much—or ever—but: The Peninsula is maybe our favorite urban hotel in the entire country. It was recently renovated, which, in this case, means new custom artwork in the guest rooms (including silk floral wall prints), tablet technology for controlling everything (lights, curtains, room service) by touchpad, and a new cocktail lounge, Z Bar, perched high above Michigan Avenue, where drinks are made tableside on a roving cart. Sipping an Old Fashioned here while soaking in the rooftop views before heading to your room and falling asleep on Pretesi linens in one of the Peninsula’s supremely comfortable beds…this is the perfect Chicago evening.
Waldorf Astoria Chicago
11 E. Walton St., Gold Coast
The Waldorf’s massive, elegantly appointed guestrooms—a good portion of which have working fireplaces—are just one of the many reasons why we chose it as our home away from home during the Chicago goop pop (it actually used to be the Elysian, another goop fave). Here, a heated porte-cochère (a godsend during those brutal Midwestern winters) gives you the sense that comfort is taken very seriously before you even step through the doors. Balsan, the on-site bistro, has a solid selection of classic American fare (burgers, salads, and super fresh oysters), so leaving the grounds for a great market-driven meal isn’t a necessity.
The Langham Chicago
330 N. Wabash Ave., Magnificent Mile
Only a few years old, this 300+ room hotel takes up the first 13 floors of the Mies van der Rohe-designed IBM building (it’s actually the architect’s final work) but feels more like a boutique operation rather than a corporate-y behemoth. That said, it’s well equipped to host both business and leisure-minded travelers: spacious rooms, a choice of on-site restaurants, and a killer spa. It also offers all the thoughtful extras one might expect from a Langham, including afternoon tea service and a mini fleet of the signature pink taxis.
Longman & Eagle
2657 N. Kedzie Ave., Logan Square
This is easily the hippest hotel in town, and at only 6 rooms strong, it’s also the tiniest. But what it lacks in size and fancy amenities (there’s no concierge or room service) it totally makes up for in fun and food. For one thing, the open-plan rooms are exceptionally designed (terrariums, freestanding tubs, custom furniture handmade by the owners) with hilarious little details like vintage Fisher Price tape decks and PBR in the mini fridge. The guesthouse sits directly on top of its namesake Michelin star restaurant, which means that wild boar sloppy joes and over 150 varieties of whiskey are literally steps away. Understandably evenings tend to get rowdy, so keep that in mind when booking.