7 Chicago Hotels that Make Your Stay an Experience in Itself

By Tiffany Mast

When you’re hard pressed for time on a business trip, one way to enjoy a city is to book a boutique hotel that makes your stay an experience in itself. From swanky rooftop bars and modern amenities to craft cocktails and custom menus, these seven Chicago hotels have got you covered.

The Virgin Hotel

The Virgin brand is known for it’s purple inflight mood lighting and eccentric branding, and while the lobby is done up in deep hues of the hotel’s signature red, the rooms at The Virgin Hotel are quite the opposite. The white and gray aesthetic offer a cool, calming space with surprising little features to kick your experience up a notch.

For starters (important things first, right?) the mini bar snacks are priced at market cost, so you won’t have to pay $6 for a Twinkie. And yes, you read that correctly. Along with a Chicago-style popcorn blend, protein bars and M&Ms, they stock the mini bar with Twinkies. The room is also ideal for business travelers needing a quick space to work. The headboard is specifically designed to offer lower lumbar support, perfect for working from bed, and there is also a table workspace.

Upstairs, The Virgin Hotel hosts a swanky downtown rooftop bar with views of the surrounding skyscrapers. And downstairs, you’ll find a hip coffee shop and a restaurant for a bite to eat, equipped with outdoor swingset seats. The Virgin Hotel is conveniently steps from the attractions of Millennium Park and the Loop and a short walk or L Train ride from the West Loop foodie scene, but far enough away that you’ll get a quiet night of sleep.

Dana Hotel and Spa

The Dana Hotel and Spa, highlights its tranquil offerings for good reason. In addition to a 24/7 fitness center with access to a steam room, this hotel provides a variety of spa services for guests. The guest rooms are very modern, on par with what you’d expect to see in some popular Las Vegas hotels, like glass walls and spa-inspired rain showers.

The staff is incredibly nice and a full concierge service is happy to help you arrange any travel plans as needed. On the first floor you’ll find an amazing restaurant with really good coffee, and there’s a bar on the second floor. But perhaps most exciting is the rooftop bar. The Dana refreshed its rooftop bar, Apogee, in 2013, with turf, firepits, cushioned couches and chairs, creating a comfortable outdoor space with urban views.

The Dana Hotel and Spa is located in River North, offering easy access to the Magnificent Mile and the rest of downtown Chicago.

Kimpton Gray

The Kimpton properties are known for converting historic buildings into hotels, and this Kimpton Gray in Chicago is no exception. Once an office building, the Kimpton Gray now offers an elevated hotel experience in their marble-clad interiors. The rooms stick to the gray color palette as well and the luxurious bathrooms will give you bathtub goals, if that’s even a thing.

On-site you can enjoy Vol. 39, a law library-themed bar, or Boleo, the Kimpton Gray’s Argentinean-inspired rooftop lounge featuring craft cocktails, Latin American street food and live music.

The property also boasts all the usual amenities of a Kimpton including loaner bikes, complimentary morning coffee and tea service, and a hosted evening wine happy hour. The hotel’s downtown location makes it easy to get around.

Chicago Athletic Association

In 2015, the historic Chicago Athletic Association was reopened to the public as a boutique hotel. The ornate building originally housed an athletic club where Chicago’s wealthy could exercise, enjoy fine dining and relax in a comfortable room for the evening.

Today visitors staying at the hotel flock to Cindy’s rooftop bar for boozy popsicles, delicious cocktails and skyline views of downtown Chicago towards Lake Michigan, and enjoy throwback-style vintage furnishing throughout hotels rooms, suites, and spaces.

Located right in the Loop across from Millennium Park, the Chicago Athletic Association is in the heart of Chicago on Michigan Ave. Most downtown spots are easily walkable from here, or just a short cab or L train ride away.

The Freehand Hotel

This bohemian hotel/hostel definitely strays from your run-of-the-mill hotel chain. While the word hostel would typically deter business travelers, this property is simply a mix of more traditional hotel rooms and social hostel-style shared rooms. It’s ideal for travelers who appreciate an instagrammable space, love being surrounded by lots of greenery and can’t wait to order the avocado toast from Cafe Integral downstairs.

While the private rooms are a bit small they are the perfect quiet space to kick up your feet in the evening. The desk space is also on the small size, but you can just set up shop in the cafe or bar downstairs.

The concierge at the front desk will happily point you in the direction of anything you need, like the most photogenic views of the city. And given The Freehand Hotel’s ideal location in River North, you’re just steps from the Magnificent Mile for shopping and the riverwalk (where we highly recommend hopping on the Architecture Boat tour if you have an hour and a half to spare), and a short walk from the Loop.

ACME Hotel Company

The Acme Hotel is located right next store to The Freehand Hotel, so it’s equally well positioned in the River North neighborhood. Downstairs, you have got to stop in to West Town Bakery to try the doughssant.

Those who check in here will find awesome extras for business travelers like free hotspots to go and complimentary coffee delivery to your room. And the tech lovers will enjoy taking the hotel’s complimentary Apple watches and Snapchat Spectacles for a spin.

And when you have time between meetings, The Acme Hotel offers a curated list of cool attractions and events around the city.

The Robey Hall

While The Robey at over $200/night is a bit of a business travel splurge, The Robey Hall, Wicker Park and Bucktown’s newest designer hotel, is much more “trip budget” friendly. And it’s right next door!

Built in the historic Hollander Fireproof Warehouse, The Robey Hall sits between The Robey and the Damen Station on the blue line of the L train, making it easy to get downtown quickly. And this neighborhood offers guests a variety of galleries, cafes, studios, independent boutiques, nightlife, street fashion, and live music venues to explore.

Inside The Robey Hall, you can find an ever changing schedule of live music and interesting happenings. The onsite bar serves local beer, classic cocktails, and coffee from local favorite Metric Coffee Co.

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