8 Hot Hotels to Book for Your Next Chicago Getaway

Think of Richard Branson’s Virgin Hotels debut like the Southwest Airlines of the hotel world, only better. The brand mantra: no more nickel and diming. Instead, you’ll find zero cancellation fees or penalties for late check-out, minibars stocked at street prices, and free happy hours every night of the week. Hotel rooms (called ‘chambers’) feature one-of-a-kind lounge beds with ergonomic headboards and erectable footboards, making it easier to work and hang out in comfort, and you can order room service, an extra toothbrush, or even control the room temp all through a convenient mobile app. (Travel with Fluffy often? Dog-friendly chambers come with separate dog beds.) The hotel recently brought on Top Chef contestant Rebecca LaMalfa, so expect to see elevated menus at the four food and booze spots around the hotel.

Originally built in the 1890s, the stunning, masterful Chicago Athletic Association building opened to the public last year after undergoing a major revamp. Vintage chandeliers, stained glass windows, massive fireplaces, and original mosaic-tiled floors were left intact, while new dining establishments—including Shake Shack and the Cherry Circle Room, where you’ll find a raw bar alongside American classics—cater to the hip at heart. Sport and play is still top of mind here. By day, borrow one of the hotel’s custom-designed tandem bicycles for a spin around the city; by night, you’ll find guests in the cavern-like Game Room competing in rounds of shuffleboard, bocce, chess, checkers, and billiards while sipping on hand-crafted cocktails.

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The Freehand may be one of the more affordable stays in lively River North, but it’s a far cry from those joints you likely booked in college during that semester abroad. The proof: a high-design aesthetic and thoughtful gathering spaces including a stylish breakfast and coffee café and the Broken Shaker Bar, whose outpost at the Miami Freehand was nominated for a James Beard Award. At this hotel-hostel hybrid, take your pick among private rooms, shared quads (where privacy curtains make snoozing next to a stranger less awkward), or one of two penthouses, which have living areas and two bedrooms apiece—perfect for traveling groups.

The 60-story skyscraper was built with a 1920s Parisian grand dame in mind, and it’s those European design influences (including a brick-paved drive and stunning white marble lobby with a centerpiece chandelier) that make this romantic Gold Coast neighborhood stunner the perfect setting for a couple’s weekend away. A new cobblestone patio is open for outdoor dining as well as a pop-up restaurant concept called the Kitchen, which features a menu built to complement the flavor notes found in champagne. For extra pampering, don’t forget to book a lava-shell massage in the tranquil downstairs spa.

A predominantly under-40 crowd digs the young, tech-savvy personality of this 130-room hotel right off the Magnificent Mile. Neon signs, industrial pipes, chalkboards, and elevators lined with album covers lend it an artsy vibe, while gadgets like Apple watches and even Google Glass are on loan for guests looking to unleash their inner nerd. Hit up the West Town Bakery for pastries and coffee in the a.m., then, come evening, kick back with a barrel-aged bourbon cocktail in hand at the see-and-be-seen Berkshire Room lounge.

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Looking to avoid Chicago’s tourist-packed Mag Mile and get a more authentic city experience? Lincoln Park’s boutique Hotel Lincoln grants the best of both worlds: it sits across the street from the popular, picturesque Lincoln Park Zoo and conservatory but is just far enough away from downtown to feel like an escape. The hotel’s buzzy first floor restaurant, Perennial Virant, specializes in seasonal farm-to-table fare (psst: go for the brunch) while the rooftop dining and cocktail spot, J. Parker, became an instant neighborhood hit thanks to its sunset drinks and some of the best views of the city.

June saw this nearly 100-year-old structure, formerly the 1923 London Guarantee Building, reopen as a 452-room hotel complete with a new glass tower that overlooks the Chicago River. The restored interior, defined by subtle jazz-themed motifs that pay homage to its former life as a 50s music club, juxtaposes the original building’s classic details—including the gold-leaf ceiling in the rotunda—alongside more modern ones like custom artwork and keyless room entry. The biggest draw, however, might be LH, the city’s first tri-level rooftop bar that serves retro cocktails and delectable shared plates against a backdrop of skyscrapers.

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This 40-room boutique and social club is where Chicago’s creative class comes to work and play. Throughout the day, visitors spend their free hours bouncing between the cozy fifth-floor ‘club’ (where you’ll find a grand piano, fireplace, plush velvet couches, and Ping-Pong tables), the movie screening room, rooftop pool and outdoor deck, gorgeous wood-paneled fitness center (fitted with a full-size boxing ring), and lower-level Cowshed Spa. Small, charming features like tea sets and Persian rugs give the hotel rooms, which range in size, a homey touch.