Hotels Trip Ideas building outdoor metropolitan area metropolis City urban area people skyscraper neighbourhood road Downtown human settlement cityscape street group tourism skyline plaza pedestrian public transport several crowd
Hotels

8 Hot Hotels to Book for Your Next Chicago Getaway

Chi-town's hottest hotel openings are causing a stir thanks to heavy doses of style and—for some—reclaimed historic buildings unique to the Windy City. These are our new favorite stays in Chi-Town.

See recent posts by Kristen Dold l Photo by Tom Rossiter for Goettsch Partners

Hip Hotels Living Lobby Lounge Modern indoor ceiling room interior design estate Boutique tourist attraction living room hall decorated
1

Virgin Hotels Chicago

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.

Check Prices for Virgin Hotels Chicago in Chicago, IL

Loading Price
Fireplace Hip Historic Hotels Living Lobby Lounge Modern indoor room flower estate interior design home living room altar mansion decorated furniture
2

Chicago Athletic Association

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.

RELATED: It's All Fun and Games at These 10 Hotels

Check Prices for Chicago Athletic Association in Chicago, IL

Loading Price
Bedroom Budget Hotels Lounge Suite wall indoor floor room Living property home hardwood interior design living room cottage flooring Design furniture real estate estate apartment area wood
3

Freehand Chicago

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.

Check Prices for Freehand Chicago in Chicago, IL

Loading Price
Hotels floor property room indoor swimming pool bathtub interior design estate home flooring daylighting Design living room bathroom mansion area furniture
4

Waldorf Astoria Chicago

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.

Check Prices for Waldorf Astoria Chicago in Chicago, IL

Loading Price
Budget Dining Hip Hotels Luxury Modern indoor restaurant interior design Bar lighting Lobby several
5

ACME Hotel Company Chicago

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.

RELATED: 24 Fruity Cocktails for the Summer

Check Prices for ACME Hotel Company Chicago in Chicago, IL

Loading Price
Bedroom Hip Historic Hotels Living Lounge Modern Suite indoor wall room ceiling property furniture home interior design living room estate real estate cottage apartment area several
6

Hotel Lincoln

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.

Check Prices for Hotel Lincoln in Chicago, IL

Loading Price
artistic artsy chic cozy Hip Hotels library living area Lounge Luxury neutral tones regal sophisticated trendy floor chair indoor living room furniture room interior design home Design table leather

Photo by Nicholas James Photography

7

LondonHouse Chicago

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.

RELATED: The World's Best Rooftop Bars

Check Prices for LondonHouse Chicago, Curio Collection by Hilton in Chicago, IL

Loading Price
Hotels indoor wall floor room property living room estate home interior design furniture Suite cottage real estate Bedroom Design mansion farmhouse apartment
8

Soho House Chicago

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.

Check Prices for Soho House Chicago in Chicago, IL

Loading Price

Want more?

All products are independently selected by our writers and editors. If you buy something through our links, Jetsetter may earn an affiliate commission.