Our 18 Favorite Chicago Hotels, and the Best Use Case for Each

From blissful staycations to a place to stash in-laws

Calling a hotel “the best” is a subjective endeavor. For some, it’s all about location. For others, an impeccable room is the only requirement. Then there are those who need a quirky amenity or two to tip the scale.

But there’s no need to choose a favorite here.

Because today, we’ve compiled a list of 18 superlatives to celebrate Chicago’s top hotels for a variety of predilections and use cases. Looking for value? Square footage? Instagrammability? Excellent robes? We’ve got the best for each and more, in no particular order.

Most Impressive Lobby: Palmer House (See image above)
Sure, the latest hotel trend is toward the sleek and modern, but sometimes you can’t beat a little Gatsbyan excess. Palmer House is second to none: 24-carat gilded columns, 21 mural panels of Greek mythology painted on the ceiling, one-ton chandeliers. It’s opulent and enduring — the longest continually operating hotel in the United States, in fact. Charles freakin Dickens stayed here. So did Oscar Wilde, Frank Sinatra, Judy Garland, Louis Armstrong and Liberace. The last one seems a bit obvious, given the lobby.

Best Bang for Your Buck: Kimpton Gray Hotel
Location is great, but you make your money back in hotel amenities and The Gray packs them in: a nightly boozy social hour in the lobby, loaner bikes to tool around town, Peloton bikes in the on-site gym, lululemon clothing to borrow for your workout, Tie Bar pieces stocked in the mini-bars and a free library of children’s books for the kiddos. Something for everyone and standard rooms hover around $115 a night.

Rookie of the Year: Sophy Hyde Park
Finally there’s a boutique hotel on the South Side! Academic, historical and artistic, Sophy puts you in the action if you’re visiting the Museum of Science and Industry or University of Chicago. If you call yourself a Chicagoan but haven’t wandered through Jackson Park and seen The Statue of the Republic, it’s time to book a room.

Suite Most Likely to Have Its Own Zip Code: Trump International Hotel & Tower Chicago
Shocker … the largest suite in the city is in the Trump Hotel — or, as the owner might say, “It’s a VERY big room. The biggest room! People are really talking about how big this room is.” Or, in layman’s terms: 3,876 square feet, 10-foot floor-to-ceiling windows, 65” Samsung TV and a fully equipped kitchen with Sub-Zero and Miele appliances (in the fourth tallest building in the United States, to boot).

Most Easily Confused for an Art Gallery: The Blackstone, Autograph Collection
Some 1,600 pieces of art adorn the guest rooms, meeting rooms and hallways of this Michigan Avenue classic. The hotel of choice for 12 consecutive US Presidents (including Teddy Roosevelt and JFK) today, The Blackstone hosts an in-flux gallery of works by in-demand local artists, some on sale if you’re in the market.

Fittest Hotel: The Hotel at Midtown
Guests gain access to the Midtown Athletic Club and you’ll need the hotel room to pass out in after you’ve cycled through one of the world’s largest indoor tennis centers, two Olympic-length pools, a boxing gym, cycle studio and golf simulators. If you’re an ace, pop for one of the suites, designed by Venus Williams.

Rarest Amenity That Is Actually Quite Useful: The Majestic Hotel
Most hotel gyms are not the Midtown Athletic Club. For the times you crave the vibe of a normal gym, and all the equipment that comes with it, look for hotels like this Lakeview boutique that doles out passes to the Fitness Formula Club next door.

Slickest Hotel Robes: ACE Hotel
ACE isn’t like a regular hotel … it’s a cool hotel. The Fulton Market newbie is making some noise and even their robes break with tradition. A cross between a boxing robe and your favorite hooded sweatshirt, robe up in terrycloth goodness and order The Burger and Fries — you’re dining in.

Best Accessible Hotel: Park Hyatt
This top-tier luxury hotel delivers the best for all guests. Easy Access Chicago gives it top marks in hearing, vision and mobility categories. Accessible public areas and restaurants like NoMI give way to 12 wheelchair adapted rooms, three of which have roll-in showers. Park Hyatt’s location also puts travelers two blocks from the L for easy transport throughout the city.

Most ‘Grammable: Chicago Athletic Association Hotel
Are you even surprised? The Venetian Gothic exterior. The old-school interiors with heavy woods, leaded glass and carved marble. The kitschy vintage sporting equipment. The bars (Cindy’s Rooftop and Happy’s). THE VIEW. #doitforthegram

Sceniest: ACME Hotel
The Berkshire Room’s award-winning craft cocktail scene is legendary (Dealer’s Choice anyone?) and now they’ve added Bunny Slope, a subterranean après-ski themed lounge featuring an indoor jacuzzi and wood-paneled walls. Of course guest rooms include an Amazon Echo and suites are fitted with ESP Guitars. Party on.

Best Late Night Food: Moxy Chicago
Is it weird that more hotels don’t have a 24-hour walk-up taco counter? Zombie Taco is ready and waiting any time of day to hit the spot, or when you’re brave enough to tackle their 17-pound burrito.

Best Urban Respite: Hyatt Lodge at McDonald’s
Ditch the grind and head to Oak Brook, where the Mies van der Rohe-inspired Hyatt Lodge awaits. Surrounded by 88 acres of forest preserve and scenic lakes, it’s a perfect location to catch your breath. Trek for miles on wooded walking paths then melt into the striking glass-ceiling pool and hot tub. Plus, Butler National is five minutes away. Pack your sticks.

The Filet Mignon aka The Best Hotel for a Steak-cation: The Rose Hotel
Rosemont’s brand new boutique hotel is the prime location to enjoy Chicago’s favorite steakhouses: Morton’s, Carmine’s, Gene and Georgetti, Gibson’s, Harry Caray’s, The Capital Grille, Fogo de Chao, Hugo’s Frog Bar. Holy Cow! When the meat sweats hit, use the hotel’s pillow menu to customize your snooze — a rare amenity. Steak your claim on one of these rooms. Meat you there. Okay, I’m done. Well done.

Hotel Most Likely to Trick You Into Thinking You’re on a European Vacation: The Herrington Inn & Spa
Forty-five minutes out of the city but a world away, The Herrington (and Geneva) reads European. From the balcony, it’s hard to tell if you’re peering down the Fox River or the Danube. This romantic, AAA diamond haven feels straight out of Bavaria.

Techiest Experience: Conrad Chicago
Haven’t quite gotten into the VR craze? Well if you’re a whisky fan, we’ve got the perfect foray. At Baptiste & Bottle, the hotel’s cocktail bar, strap on a virtual-reality headset and fully immerse into the journey of your Macallan Cocktail, from farm to tongue.

Best Online Booking Tool: Hilton Honors App
Not a hotel per se, but an outstanding experience that puts this chain above the rest. Preferred guests pick their actual room from their phone at check-in time. Never again will you end up sandwiched between the ice machine and the elevator.

Best Alternative to an Airbnb: Fieldhouse Jones
Traveling with a group? On a tight budget? Looking for a friendly hostel? Fieldhouse Jones has a plethora of lodging options, from private bedrooms to bunk rooms and even apartment setups, and Airbnb ain’t got nothing on the decked-out communal spaces here.

All images via the attendant hotels; main image via Palmer House


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