Last Updated February 21, 2019 2/21/2019

Top 8 Boutique Hotels in Chicago

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Chicago has absolutely everything you’d ever want in a city, including world-class attractions, amazing restaurants, and big luxurious hotels. However, there are also some excellent boutique hotels that offer an intimate vibe and really help you get to know the city on a personal level. By staying at a boutique Chicago hotel, you can connect with other travelers, explore the local scene, and have all the comforts of home in a unique and inspiring environment. Here are eight of our favorite boutique hotels in Chicago for your next Midwestern journey.

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Ivy Boutique Hotel
Ivy Boutique Hotel

Ivy Boutique Hotel

The Ivy Boutique Hotel has 63 guest rooms and stands 16 stories tall, just a few steps away from the iconic Magnificent Mile. Here you’ll have everything you need for a comfortable and convenient stay in the city and be so close to Chicago’s top attractions and restaurants. The hotel’s Divine Lounge is a great place to sip a cocktail, and there’s an outdoor lounge called the Sky Terrace where you can soak up amazing city views. Guests have access to a shared lounge area with a TV, can enjoy breakfast in their rooms, choose family rooms with more space, and use the hotel’s free Wi-Fi. Guests love the Ivy’s central location at 233 East Ontario and room service offerings.

Longman and Eagle
Longman and Eagle

Longman and Eagle

Located in the trendy Logan Square neighborhood, Longman & Eagle is best known as a hip eatery and whiskey bar. But this is also an exciting and affordable place to stay overnight. There are six rooms at this boutique hotel sitting above the tavern, which makes this ideal if you’re looking to have a few drinks and not worry about how to get to your hotel after the bar. Room offerings include smart TVs, vintage cassette tape consoles, complimentary Wi-Fi, original artwork, and curated mini bar. You’ll love exploring this hipster neighborhood and getting to know the local community when you stay overnight at Longman & Eagle.

Thompson Chicago
Thompson Chicago

Thompson Chicago

If you’re looking to stay somewhere sophisticated and stylish in the Gold Coast neighborhood of Chicago, then the Thompson Chicago is an excellent pick. This is one of the best hotels in Chicago that happens to also be a boutique hotel, which is beautifully designed and truly embraces luxury. It’s also on the edge of Michigan Avenue and the Magnificent Mile, as well as close to Lake Michigan. There are 247 rooms in this hotel, which is surrounded by designer boutique shops and lovely tree-lined streets. The rooms overlook one of the city’s most celebrated neighborhoods and offers floor-to-ceiling views of the city skyline. Make sure to enjoy a meal at Nico Osteria for Italian seafood and homemade pastas when you stay here. Salone Nico is an excellent cocktail lounge inside the Thompson Chicago that has a European flair and amazing wines from Greece and Italy.

The Guesthouse Hotel
Inside The Guesthouse Hotel

The Guesthouse Hotel

The Guesthouse Hotel in Chicago is a great boutique hotel for business travelers, families, and solo travelers too. With just 25 units at this boutique hotel, the Guesthouse Hotel offers one-, two-, and three-bedroom accommodations. When you stay here, you’ll be in the heart of the Andersonville neighborhood, which is quaint, full of local culture, and packed with great restaurants and bars. This is also a pet-friendly option for well-behaved dogs of all shapes and sizes and at no extra charge. The hotel even offers complimentary food and water bowls, beds, and baggies upon request. In-room spa services are offered courtesy of the hotel’s neighbor, Revive Massage Therapy and Spa. Other features include a fitness center, rooftop deck, kids’ activities for rainy days, and in-room dining with local restaurants like the Southport Grocery and Café and Calo Ristorante. Extended stay options are also available here for travelers looking for short-term housing.

Kimpton Hotel Palomar Chicago
Kimpton Hotel Palomar Chicago

Kimpton Hotel Palomar Chicago

You can also book a room at the luxury boutique hotel in the River North neighborhood of Chicago called the Kimpton Hotel Palomar. This welcoming hotel is a sophisticated place to stay with large guest rooms and suites, as well as a 17th-floor pool and terrace. There is also Sable Kitchen & Bar here, impressive views of the skyline, a popular wine hour, and wellness programs for guests. When you stay here, you’ll be within about a ten-minute walk from the Riverwalk, River North’s dining and nightlife scene, and the Merchandise Mart. The list of amenities offered at the Kimpton Hotel Palomar Chicago includes complimentary PUBLIC bikes, in-room yoga mats, and 24-hour fitness center, complimentary coffee and tea, and family accommodations. There are pet-friendly rooms here too if you are traveling with your pup.

The Robey

The Robey

Meanwhile, the Robey is a boutique hotel on the northwest side of Chicago that is unique and designed-oriented. This hotel is in the hip Bucktown-Wicker Park area of the city at the exciting intersection of Milwaukee, Damen, and North. It’s an art deco masterpiece that’s 203 feet tall, dates back to 1929, and has 89 rooms. Guests stay in the tower rooms and the annex lofts and enjoy perks like Wi-Fi, easy access to the Blue Line “L” train, the UP Room rooftop cocktail bar, and Cabana Club’s indoor/outdoor cocktail bar and rooftop pool. There’s a great lounge here for your workspace, Chef Kevin McAllister serves Modern American cuisine onsite for brunch and dinner, and the pool is open from May through September.

Soho House Chicago
Soho House Chicago

Soho House Chicago

Located in the Fulton Market District, the Soho House Chicago doubles as both a hotel and a members’ club. Local members and hotel guests can use the event spaces here, and Soho is also home to the Cowshed Spa. Choose among options for small-, medium-, and large-size bedrooms here. The House Kitchen is a rustic wood grill with seasonal and local ingredients, and there’s a 17,000-square-foot gym on the second floor.

Freehand Chicago
Inside the Freehand Chicago

Freehand Chicago

The last awesome boutique hotel we’ll highlight here is Freehand Chicago in the River North neighborhood. Here you’ll find multiple room options, a fitness center, all-day food and drink menu, complimentary Wi-Fi, guest kitchen and lounge, and affordable parking. Cafe Integral here serves delicious Nicaraguan coffee, teas, and juices, and the Broken Shaker is the place to be for handcrafted cocktails.

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