The Best Hotels in Chicago

Dan Angell is a longtime traveler and writer who’s always in search of the best restaurants and most unique experiences in every city he visits. He makes his home in Indianapolis, in part because of how easy travel is from the Crossroads of America.

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Having the right hotel in Chicago is the first step to making the most out of everything the Windy City offers. Whether it’s comfortable beds, location, great views, or affordable prices, these hotels all offer something special that makes them the best in Chicago. 

The Langham

Front entrance of The Langham with old pink cab out front.
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If your idea of a memorable Chicago vacation involves shopping and self-care, The Langham is the ideal place to stay. Located within walking distance of Michigan Avenue, nicknamed the Magnificent Mile, this hotel makes it easy to get to the city’s best shops and restaurants. 

The hotel boasts large, luxurious bathrooms with rain showers, a 67-foot-long indoor pool, a steam room, and a hot tub, plus fantastic views of both the Chicago river and the city.

The Westin Chicago River North

Aerial view of The Westin Chicago River North from across the river.
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The Westin Chicago River North is all about space and location. Offering incredible views of the city and the Chicago River, the hotel is situated just a couple of blocks away from the train station, making it easy to explore.

Inside the hotel, guests are treated to large, comfortable rooms. Head to the hotel’s 320 RiverBar restaurant for unbeatable views and service. 

The Pendry Chicago

Front entrance to the Pendry Chicago.
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As one of Chicago’s newest hotels, The Pendry Chicago provides a modern update to the historic Union Carbide and Carbon building. 

Rooms are spacious, beds are comfortable, and the black and white granite interior provides stunning examples of Art Deco architecture from a century ago.

The Pendry also sits just two blocks from the entrance to Millennium Park, making it an ideal location from which to enjoy some of Chicago’s best attractions.

The Peninsula Chicago

Exterior aerial view of The Peninsula Chicago.
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You’ve just gotten back from a long day of walking the Magnificent Mile. You’ve already eaten, and all you want to do is sit back, relax, and get some much-needed rest. The Peninsula Chicago has guests covered, as they can control temperature, curtains, lights, and interruptions all from the comfort of their bed. 

The bathrooms help handle that job as well, as they’re well-designed, spacious, and well-connected. If you’re in need of a good soak while watching a favorite show, you can do that here with televisions in the bathroom. 

The Ritz-Carlton Chicago

CHICAGO, USA - JUNE 28, 2013: People enter Ritz Carlton Hotel in Chicago. Ritz-Carlton is part of Marriott International and operates 84 luxury hotels worldwide.
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If it’s stunning views in the lap of luxury that you want, the Ritz-Carlton Chicago is your hotel. Book a room on a high floor for incredible views of Lake Michigan.

The hotel even has its own private art collection with pieces inspired by local attractions. This five-star hotel is family-friendly―diminutive bathrobes are on offer for the kids, as is a candy cart that’s sure to delight.

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The Viceroy Chicago

View of Chicago from the pool level of the Viceroy Chicago
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When summer arrives in the Windy City, there aren’t many better places to be than on top of the Viceroy Chicago. This hotel offers the best rooftop pool in the city, situated 18 stories above the Chicago traffic. The pool is only open to hotel guests, helping to prevent overcrowding.

The poolside bar is open year-round, so even when it’s too cold for a swim, guests can always go up for a drink. The hotel also sits just minutes away from the Magnificent Mile, so it’s easy to enjoy a day of shopping and quality restaurants before coming back for a relaxing dip in the pool under the Chicago skyline.

The Waldorf Astoria Chicago

Front entrance of the Waldorf Astoria Chicago
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Situated in one of Chicago’s tallest and most historic buildings, The Waldorf Astoria sits just off the Gold Coast, providing some incredible views of Lake Michigan.

Separate showers, deep soaking tubs, private fireplaces, and a classic black-and-white décor make for one of the most romantic and welcoming atmospheres in the entire city.

Chicago Athletic Association Hotel

Front entrance to the Chicago Athletic Association
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You won’t be bored at the Chicago Athletic Association Hotel, a historic property that’s converted old billiard rooms into giant game rooms featuring bocce and foosball, and more in a nightclub-type atmosphere.

Suites include working fireplaces for a cozy atmosphere, and the hotel’s location offers gorgeous views of both Millennium Park and Madison Street. If you’re in Chicago to catch a Bulls or Blackhawks game, the No. 20 bus goes from the hotel right to the United Center, making this spot perfect for sports fans.

Residence Inn Downtown Chicago Loop

Front entrance of the Residence Inn Chicago Downtown/Loop with taxis driving by in a blur
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Chicago is an incredibly convenient city to get around in, as long as you’re within the area known as the Loop. The Residence Inn Downtown Chicago Loop offers easy access to bus stops and CTA train stations.

Free breakfast, comfortable rooms, and plenty of business space make the Residence Inn a great budget-friendly option for a Chicago trip. 

The Freehand Chicago

Front entrance of the Freehand Chicago with people waiting for a cab from across the street
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For an even more affordable Chicago hotel, the Freehand Chicago is the perfect choice for groups. Book a bed in a dorm-style room or reserve a private quad room for your crew.

Don’t want to share? Private rooms still offer a great price for the area, and guests will enjoy colorful décor and a top-quality bar option with some of the most creative cocktails in the city. If you’re looking to maximize your budget for the shops and restaurants of Chicago, you’ll find plenty to love about this spot.

RELATED: Best Hotels With Jacuzzis in the Room

Crown Plaza Lombard Downers Grove

Front entrance of the Crowne Plaza Lombard Downers Grove, an IHG Hotel
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Most people who visit Chicago want to pay a premium to be in the city. If you’re willing to stay outside of the city and put in some driving, you can score some incredible deals on your hotel. The Crown Plaza Lombard Downers Grove is one of those options, where you’ll find four-star quality for a two-star price.

At the Crown Plaza, you’ll find a large swimming pool, spacious and comfortable rooms, luxurious bathrooms, and plenty of peace and quiet. 

Sonesta Rosemont Chicago

View of the front exterior of the Sonesta Chicago O'Hare Airport Rosemont
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Like the Crown Plaza, the Sonesta Rosemont Chicago offers some luxurious rooms at reasonable prices because you’re staying slightly outside the city. In this case, that can still put you close to some of the action, the hotel is near the Allstate Arena and Rivers Casino.

In the hotel itself, you’ll find spacious, comfortable rooms at a fraction of the cost of a downtown stay. You’re also right by the airport, so traveling in and out of the city couldn’t be much easier.

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