North America

8 Coolest Hotels in Chicago | Rooftop Bars, In-Room Guitars, and Hipster Charms

Chicago hotels come in all shapes and styles. Local writer Jay Gentile takes you through 8 of the coolest options in the city.

With one hand, I grab the patio railing perched 13 floors above downtown Chicago overlooking views of Millennium Park and Lake Michigan. With the other, I slowly bring an expertly crafted vodka tonic to my lips. But in my mind, I find it hard not to think of myself as a modern-day version of Wall Street’s Gordon Gekko surveying his kingdom from above.

This is just another day at the Chicago Athletic Association, where locals and visitors alike mingle to take in the eye-popping scenery Cindy’s, a popular rooftop bar. The vibe is laid back and the panoramic view of Lake Michigan is stunning.

But in a city as crazy about architecture as Chicago, it’s certainly not the only hotel to cultivate a hip aesthetic paired with excellent cocktails and panoramic rooftop views. In fact, Chicago is blessed with a number of such properties–not to mention hipster-approved hotels with in-room guitars, podcast booths, and karaoke bars.

With Chicago’s hotel scene aimed at millennials in recent years, I set out to uncover the coolest hotels in a city with plenty of them. So book your stay at one the hotels below and immediately become one of the cool kids.

Join the club at the Chicago Athletic Association


It’s hard to be more centrally located in Chicago than the Chicago Athletic Association, perched over downtown’s Millennium Park in a recently renovated 1893 landmark building. The former private club was reopened to the public in 2015 as a bustling 241-room hotel, helping to usher in Chicago’s current hotel Renaissance. But the CAA isn’t just a hotel, it’s a destination in itself.

Complete with seven on-site bars and restaurants, the hotel offers guests a taste of Chicago’s past, present, and future through a variety of interesting spaces including the bocce ball-equipped Game Room, the eight-seat microbar and former speakeasy Milk Room, classy throwback eatery Cherry Circle Room, and even its own Shake Shack location. But the top draw here is Cindy’s, the hotel’s stunning rooftop bar and central meeting place for downtown’s in-crowd unfurling one of the finest panoramic views in the city overlooking Lake Michigan from the 13th floor.

Bring cocktails back to your Millennium King room overlooking Millennium Park or get cozy under the covers in one of the hotel’s classic or superior rooms, all of which are comfortable and stylish without trying too hard–sort of like the city itself. In addition to the park, you’re within easy walking distance to many of Chicago’s top attractions including the Art Institute of Chicago and the Chicago Riverwalk.

Chicago Athletic Association, Part Of Hyatt

Top rated
9.1 Excellent (4539 reviews)

Drink tiki cocktails at local “poshtel" Freehand Chicago


One of the first and finest examples of Chicago’s upscale hostel-style “poshtels” to have opened in recent years, Freehand Chicago has helped lead the charge in downtown’s diversification from more traditional high-end stuffy hotels to those that cater more towards a millennial demographic. The first thing you’ll need to attract such guests is a cool cocktail bar, and the Freehand has one of the best in the city.

Often grabbing more headlines than the hotel itself, The Broken Shaker is the Freehand’s award-winning cocktail emporium where some of the city’s top mixologists are slinging a slew of hipster-inspired cocktails including Cocoa Puff-infused Old Fashioneds. With retro wallpaper and a tiki-meets-Miami vibe, The Broken Shaker (modeled after its original Miami location) can be counted on to cultivate an ultra-cool scene with live bands, DJs, and a street-food style menu of small bites like fried chicken sandwiches or vegan sausage “fo’ boys. If you aren’t in the mood to booze (or are recovering from a long night at Broken Shaker), hit The Freehand’s Café Integral for some fancy Nicaraguan coffee.

Unlike most traditional hostels, The Freehand offers a variety of private rooms including a duplex penthouse in addition to shared quad rooms that can also be rented out for private groups. You’re also within easy walking distance of many of Chicago’s top bars and restaurants, including the speakeasy-style tiki hotspot Three Dots and a Dash.

Freehand Chicago

8.0 Very good (3085 reviews)

Rent out your own ski bar with hot tub at Acme Hotel Company


What hotel has in-suite guitars and its very own hot tub-equipped après ski bar that you can rent out with 17 of your friends? This hotel. As if created in a lab in order to maximize your cool points, it’s hard to get more hip than downtown mainstay Acme Hotel Company, which opened in 2012 next door to what is now the Freehand Chicago.

Get the party started by grabbing some suds from your in-room beer vending machine or mix up a stiff one using your DIY cocktail kit before heading to the hotel’s excellent cocktail bar Berkshire Room, famous for their “dealer’s choice” cocktail where you name your spirit and flavor profile and their top-flight mixologists do the rest. As for that ski bar with a hot tub? It’s called Bunny Slope and it’s available for private bookings only, although hotel guests are allowed in when it’s not booked. In addition to the hotel’s communal workspace and Bare Painted Ladies mannequin art installation, rooms also come equipped with plenty of high-tech flourishes including state-of-the-art wireless audio systems and Amazon Echos.

Rooms are outfitted with fashionable wall art and 300 thread-count Egyptian cotton beds, although you’ll probably be too busy boozing and rocking to spend much time there. And in case you do overindulge, not to worry: there are even hangover kits equipped with Gatorade, aspirin, and local burger shop gift certificates as part of the hotel’s “Hair of the Dog” package.

Acme Hotel Company

Top rated
9.0 Excellent (2887 reviews)

Play guitars and turntables from your room at Ace Chicago


With the Ace Hotel brand well known for cultivating some of the coolest hotels in the United States and beyond, Ace Chicago is no different with a hipster-approved space popping up in 2017 in an industrial concrete and glass building in the city’s increasingly cool West Loop neighborhood.

Not only does the hotel offer rooms equipped with Martin acoustic guitars and/or turntables with a curated selection of vinyl, but the hotel also hosts its own summer music festival called Double Vision on its rooftop bar Waydown. Well known as one of the coolest rooftop bars in the city, the festival features live bands and DJs performing from July 21-August 4 in the days between Chicago’s Pitchfork and Lollapalooza music festivals. (As part of the hotel’s Double Vision package, you can also get hangover fighting “Morning Oasis” access at Waydown complete with B12 shots and massage chairs.) But even if you’re not here to party till dawn with the music festival kids, Waydown should be on your radar as should the hotel’s standout restaurant City Mouse, where the weekend brunch burrito and corned Wagyu beef is a force to be reckoned with.

Rooms come in a loft, suite, or standard variety, with Bluetooth radio and some rooms offering prime skyline views. Fuel up for your big day at the on-site location of highly acclaimed Stumptown Coffee Roasters (their first Midwest outpost) and be sure to check out rotating exhibits in the hotel’s gallery space.

The Emily Hotel

Top rated
9.0 Excellent (1124 reviews)

Perch yourself atop one of Chicago's coolest hoods at The Robey


If you want to get out of more touristy downtown areas and into the more neighborhood-centric enclaves where the “real” Chicagoans live, you could do far worse than booking a stay at The Robey. Situated in the heart of Chicago’s trendy Wicker Park neighborhood, this stunning space was opened in 2016 inside a historic Art Deco building designed in 1929.

As the tallest building for miles, The Robey is famous for its fantastic 13th-floor rooftop bar The Up Room, where you can enjoy unobstructed views of the city all the way to Lake Michigan. But that’s not all that’s on offer here. If you’re lucky enough to visit Chicago in summer, you can also take advantage of the Robey’s sixth-floor cocktail bar with rooftop pool Cabana Club. If you get hungry you can grab a bite of seasonal comfort food from Café Robey or chill with occasional live bands or DJs on the second-floor lounge. More fitness-conscious guests can take advantage of free bikes for hire as well as full access to Bucktown Athletic Club next door.

The 89-room hotel offers 69 standards yet chic and sunny Tower Rooms in addition to 20 warehouse-style Loft Rooms with 10-foot ceilings, concrete floors, and flexible multi-bed configurations. You’re steps from Chicago’s Damen Avenue subway stop as well as some of the coolest bars and restaurants in town, including the always packed and in-demand outdoor patio at hip taqueria Big Star. Ride your bike or take a short walk to Chicago’s 606 urban hiking trail perched along a former railway line for elevated views of the city cutting across some of Chicago’s coolest neighborhoods.

The Robey, Chicago, A Member Of Design Hotels

9.0 Excellent (1307 reviews)

Find the basement karaoke lounge at Found Chicago River North


Entering the increasingly crowded downtown hotel field in 2018 is 60-room boutique hotel Found Chicago River North, the latest spot in the city to offer shared accommodations geared towards younger travelers. While the 1910s-era building housing the hotel at one time offered shabby single room occupancy (SRO) rooms, today that sketchy vibe is long gone while the space still manages to offer some of the most affordable options in the city.

Found is most famous for its dimly lit basement Asian-inspired karaoke lounge Blind Dragon, where you can choose from more than 25,000 songs as you sip exotic cocktails, punch bowls, and sakes with private karaoke suites also available. The hotel’s restaurant Mason goes off in a more upscale direction with caviar dip and filet mignon, while its coffee shop Mason&Mason keeps things simple with gourmet coffee paired with breakfast and lunch items including fried egg and turkey sandwiches.

Bunks in one of its nine shared rooms can be had for as low as $24 a night. Found also offers a number of private queen and twin rooms which are low on excess frills and gimmicks but high on comfort and design, needing little but simple walnut woods and soft paint colors to create a relaxing apartment-style vibe.

Found Chicago River North


Record your next podcast at Moxy Chicago Downtown


If your “must-have” list of hotel amenities includes a podcast booth and a vinyl library, Moxy Chicago Downtown is calling (or, more likely, texting) your name with an endless assortment of millennial-geared twists like a 24/7 taco window and custom art installations meant to serve as social media backdrops when you message with neighboring guestrooms.

There’s no standard check-in service here. You check-in at the Bar Moxy, which hosts DJ series and an “Adulting Is Hard” happy hour while the hotel’s comfortable Game Room is packed with vintage arcade games like Pac-Man in addition to shuffleboard and foosball. The podcast booth hosts live recordings of top local podcasters like Podlander Drunkcast and Stories We’d Tell in Bars, while the taco window Zombie Taco slings an array of surprisingly authentic Mexican fare including the ridiculously massive 17-pound Zombie Burrito.

Pet-friendly rooms at the 156-room property are equipped with plush bedding and 49-inch smart TVs with a range of options from bunk beds to exclusive “Inner Circle” rooms which face the Garden of Eden-style courtyard art installation while graffiti art lines the stairwells. Events at Moxy include drag shows, bar crawls, and taco-eating contests, so come ready to party.

Moxy Chicago Downtown

Top rated
9.2 Excellent (1226 reviews)

Drink local beers overlooking the park at Hotel Lincoln


This neighborhood-centric spot in Chicago’s upscale Lincoln Park neighborhood has become one of Chicago’s most well-known boutique hotels since opening in 2012. The pet-friendly 184-room Hotel Lincoln, which occupies 13 floors of a storied 1928 building, is situated in one of the city’s most scenic locations overlooking Lincoln Park and North Avenue Beach.

Enjoy unrivaled views of the park, lake, and beach from Hotel Lincoln’s most famous asset: its stunning year-round rooftop bar J. Parker, named after one of President Lincoln’s bodyguards. Sip craft cans of local beer like Half Acre Daisy Cutter or Revolution Anti-Hero with a well-dressed, always lively crowd as you dig into a food menu that includes one of the best burgers in the city in addition to addictive offerings like truffle fries, pork nachos, and Thai chili chicken wings. Additional offerings at Hotel Lincoln include the highly regarded farm-to-table restaurant The Kennison and European-styled coffee bar Elaine’s Coffee Call.

With an eye towards classic Midwestern charm, basic rooms are laid-back with local artwork and 42-inch HDTVs with upgrades available in the form of one-bedroom and junior suites. While free bikes and pedicabs are available during the warmer months, the location has you within easy walking distance of some of the finest destinations in the city including the leafy Lincoln Park Zoo and iconic comedy venue The Second City.

Hotel Lincoln

8.2 Very good (2348 reviews)