The 13 best downtown Chicago hotels in the Loop

Set inside the landmark 1894 New York Life Insurance Building, The Kimpton Gray seamlessly blends Gilded Age architecture with sleek, modern luxury. Guests arrive into a lobby featuring grand staircases and Georgia Gray marble before riding one of eight restored gilded elevators to their rooms. Accommodations balance modern minimalism with nod-to-tailoring details like dark gray sectionals, black-and-blue textiles, dimmable dome lighting, and handsome black-marble bathrooms with dual sinks.

Fitness options include a 24-hour gym with Peloton bikes, plus complimentary loaner cruiser bikes at the front desk. Traveling with a four-legged friend? Pets stay for free with zero deposit, featuring lobby treat stations and in-room pet bowls upon request.

For food and drink, the property offers La Bella Trattoria on the ground level for all-day Italian fare, Vol. 39 on the second floor for law-library-inspired cocktails (featuring extensive Old Fashioned and Manhattan menus), and Boleo on the 15th floor—a vibrant South American rooftop lounge operating under a retractable glass roof.

Time Out tip: Don’t miss the complimentary daily lobby social hour from 5-6pm.

Address: 122 W Monroe St, Chicago, IL 60603
Price per night: Prices start at $164 per night 
Closest transport link: From the airport, you can take the blue line on the Chicago Transit Authority (CTA) to the Forest Park stop and the hotel will be a five-minute walk away. 

➡️ Check out Time Out’s full list of the best hotels in Chicago.

The deluxe four-star chicago hotel on Monroe simply oozes historic class. As soon as you step into the glamorous Beaux Arts lobby you’ll feel like you’ve stepped back in time, especially when gazing up at the jaw-dropping 19th-century mural on the ceiling by Louis Pierre Rigal. First built in 1871, Palmer House lasted just 13 days before burning down in the Great Chicago Fire. But, undeterred, businessman Potter Palmer got right back to work and rebuilt the hotel, launching again two years later. This time the hotel stood strong and remains in its original spot today, making it the longest continuously operating hotel in America. There’s 24-hour room service, should you fancy a snack when you stumble in late at night, which, given you’re right in the heart of Chicago, is easily done. 

Time Out tip: Try the brownies—they’re still made using a recipe invented by the hotel chef in 1893.

Address: 17 East Monroe Street, Chicago, Illinois, 60603 
Price: Standard Rooms start from $190 per night
Closest transport: Monroe station is a few minutes’ walk away, with connections on the red and blue ‘L’ trains.

➡️ Discover Time Out’s collection of the best spa hotels in Chicago

To say the Chicago Athletic Association is beautiful is to put it mildly. Stay in one of the 241 luxury boutique rooms—throwbacks to the club rooms of athletic associations long gone. Look out at Lake Michigan from Cindy’s rooftop restaurant over great food and drinks. You’ll also love the Game Room, with its private alley entrance and bocce, shuffleboard and billiards. Find access to everything you need and more in this wonderfully restored 1890s building.

Time Out tip: Believe it or not, there’s an onsite Shake Shack. It’d be rude not to grab a burger and shake… Absolutely irresistible.

Address: 12 S Michigan Ave, Chicago, IL 60603
Price: from $220 per night
Closest transport: Chicago O’Hare International Airport is a 45 minute drive.

➡️ Here’s our roundup of the most romantic hotels in Chicago

Much of the appeal of this upscale chain hotel comes from its location: occupying 18 of the 82 floors of Jeanne Gang’s stunning Aqua skyscraper, perhaps the most impactful entrant in Chicago’s Loop skyline of the 21st century so far. One of the hotel’s most attractive features is an 80,000-square-foot, third-floor green roof that boasts a scattering of fire pits. Some rooms come with private access to Gang’s unique, undulating concrete balconies, too. Oooh. 

Time Out tip: Into fitness? Don’t forget to visit the green roof. There’s a running track and junior Olympic-sized pool up there. Wowzer.

Address: 225 N. Columbus Drive, Chicago, IL 60601
Price per night: Starting from $159 during low season (November-February) and $249 during high season (May-October)
Closest transport: 10-minute walk to State/Lake L station (Brown, Green, Orange, Pink and Purple Line trains) or Lake Red Line subway; 1-hour taxi ride from O’Hare Airport and 40-minute drive from Midway Airport; 3 blocks to Millennium Station (Metra Rail)

This Loop hotel in the Reliance Building, built in 1895 and now on the National Register of Historic Places, was known as the Hotel Burnham from 1999 to 2016, when it was bought by a small West Coast boutique chain, Pineapple Hospitality, and renamed The Alise, although it’s now dubbed Staypineapple, matching another property the company owns in San Francisco. Designed by famed architect Daniel Burnham, along with Charles Atwood and John Root, the building still features the original ornate grillwork on the elevators. The ground-floor restaurant, Atwood, sports an old-world-meet-modern vibe and serves seasonal American fare alongside bespoke cocktails. Perfect for visiting architecture buffs.

Time Out tip: The encyclopedic Art Institute of Chicago is only a ten-minute walk down South Michigan Ave, with more than 300,000 artworks and artifacts from all over the world.

Address: 1 W Washington St, Chicago, IL 60602
Price: From $150 per night
Closest transport: Chicago O’Hare International Airport is a 45/50 minute drive away. 

This 27-story hotel, which completed a $32 million renovation in 2016, features 553 rooms, including 40 sprawling suites that are bigger than many condos. The location is within stumbling distance of many a fine eateries, but those who prefer to eat in are well served by the contemporary take on Chicago’s street food in Staytion Market & Bar; Raised, the rooftop terrace lounge bar, is one of our favorite sky-high spots in the city. Michigan Avenue and Navy Pier are both a 10-minute walk away, but we wouldn’t blame you for doing sweet nothing and soaking in this boutique hotel's wonderful ambience.

Time Out tip: Less than ten minutes from the northwest corner of Milennium Park, where you’ll find the Frank Gehry-designed Jay Pritzker Pavilion—home to some of the city’s biggest outdoor concerts and festivals.

Address: 1 W Wacker Dr, Chicago, IL 60601
Price: From $230 per night
Closest transport: Chicago O’Hare International Airport is between a 25–38 mins drive

Chicago’s Hyatt opened the city’s first Centric, a boutique imprint aimed at millennial travelers, in this converted 1927 office block in 2015. The 257-room hotel incorporates some of the building’s original Art Deco design touches, and features French brasserie Bandol Brasserie & Raw Bar at street level as well as a rooftop bar, AIRE, atop the 22-story structure. 

Time Out tip: Stop by The Corner before you head out for a day of exploring for complimentary coffee and snacks in a kitchen-style setting.

Address: 100 W Monroe St, Chicago, IL 60603
Price: From around $170 per night
Closest transport: Chicago O’Hare International Airport is between 30–40 mins drive

Hilton Vacation Club Hotel Blake Chicago is housed in the renovated former 19th-century headquarters of the Morton Salt Company, the historic exterior of which belies the chic, contemporary digs that live within its walls. A 24-hour complimentary business center and fitness room are just a few of the attractions. If you’re here for fun, you’re in luck. There’s an on-site restaurant, and you’re super close to some of the trendiest parts of the city.

Time Out tip: Walk east for ten minutes until you hit the beautiful spectacle that is Buckingham Fountain. Built in 1927, it features four Art Deco seahorses and Georgia pink marble, plus a holiday light and music show.

Address: 500 S Dearborn St, Chicago, IL 60605
Price: Starting from $140 per night
Closest transport: Chicago O’Hare International Airport is 30–45 min drive

A feeling of refined romance pervades in these cushy digs: oversized bathroom, separate dressing rooms, fluffy robes and a full-service spa. At the end of the evening, settle down in the lobby’s wine, cocktail and small-plates lounge for a nightcap. You can also make use of the 24-hour gym. Bliss.

Time Out tip: A ten-minute walk west will land you outside the glittering doors of the Loop’s 5,000-seat Chicago Theatre—built in 1921 and home to outstanding shows, from Eddie Vedder to Coco O’Brien.

Address: 200 N Columbus Dr, Chicago, IL 60601
Price: From $200 per night
Closest transport: Chicago O’Hare International Airport is between a 28–42 minute drive from the hotel

This 144-room boutique hotel on Jewelers Row keeps a lower profile than others, but it’s an architectural gem. The late-19th-century Arts and Crafts style is evident outside and in, with wrought-iron pieces adding accents to the comfortable (if slightly dated—let’s call it vintage) decorations in each room. There’s also room service from 7am-11pm and a 24-hour gym.

Time Out tip: Design nerds will delight in the nearby Chicago Architecture Foundation, which is worth a visit if only to marvel at its highly accurate model of Chicago, featuring 1,000 buildings in 400 city blocks glowing under simulated sunshine.

Address: 10 S Wabash Ave, Chicago, IL 60603
Price: From around $160 per night
Closest transport: Chicago O’Hare International Airport is between a 30–45 minute drive

This gorgeous hotel, first opened in 1910, has had an intriguing run so far. Many U.S. Presidents have stayed there (including Teddy Roosevelt), it was a favorite hangout of Al Capone and his cronies, and Maharishi Yogi, the Beatles’ personal guru, once owned the building. Now part of Marriott’s Autograph Collection boutique imprint, it’s simply one of the most beautiful hotels in the Loop and a favorite for bands playing at the nearby Lollapalooza music festival in August. Don’t miss the attached Spanish small-plates restaurant, Mercat a la Planxa. There’s a 24-hour gym, if that’s your vibe. There’s also a small walk to the Art Institute of Chicago, Magnificent Mile’s shops and much more. So as nice as the hotel is, you can be sure time outside won’t be anything less than great.

Time Out tip: Walk south along Michigan Avenue to access Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium.

Address: 636 S Michigan Ave, Chicago, IL 60605
Price: From $200 per night
Closest Transport: Driving? Chicago O’Hare International Airport is a 30–45 min drive away. 

There was quite a hubbub when LondonHouse finally opened in 2016. The historic landmark building is part beautiful hotel and part high-end restaurant. Guest rooms are spacious and include free Wi-Fi, large work stations and, of course, large flat-screen TVs. Many rooms also have unbeatable views of the city skyline. If you’d like, there’s a 24-hour fitness center, but we’d likely just stroll around Millennium Park, which is ten minutes away.

Time Out tip: If the idea of a great height doesn’t set your teeth a-chattering, then you’ll love LondonHouse’s rooftop bar—the only tri-level one in the city. 

Address: 85 E Wacker Dr, Chicago, IL 60601
Price: From around $240 per night
Closest transport: Chicago O’Hare Airport is roughly a 25–38 min drive from the hotel, depending on traffic. 

The lobby of this luxury Loop hotel is a stunner—all black and white marble and dramatic, curving staircases. The rooms are just as gorgeous and the spa, Valeo, is a must-visit. If you want to stay in the hotel, then, fair enough really—there’s 24-hour room service. Soak it in.

Time Out tip: Navy Pier is a short stroll—a miniature amusement park, launching point for boat tours, massive food court and home to one of the best movie theaters in town.

Address: 151 W Adams St, Chicago, IL 60603
Price: Starting from around $250 per night
Closest transport: Chicago O’Hare International Airport is between a 28–42 minute drive, depending on traffic

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