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. 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. 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. 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. 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. 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. One of the first and finest examples of Chicago’s upscale hostel-style “poshtels” to have opened in recent years, Freehand Chicagohas helped lead the charge in downtown’s diversification from more traditional high-end stuffy hotels to those that cater more towards a millennial demographic. 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. 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.īring 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. ![]() But the CAA isn’t just a hotel, it’s a destination in itself.Ĭomplete 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. 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. 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. So book your stay at one the hotels below and immediately become one of the cool kids. 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. 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. The vibe is laid back and the panoramic view of Lake Michigan is stunning.īut 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. 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. 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. ![]() With the other, I slowly bring an expertly crafted vodka tonic to my lips. ![]() ![]() With one hand, I grab the patio railing perched 13 floors above downtown Chicago overlooking views of Millennium Park and Lake Michigan.
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