Beginning of main content

Best 5 stars Hotels in Chicago

Search Flights

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Chicago Hotels

Search Flight + Hotel

Advanced options

Search 321,000 hotels worldwide.

Get the price guarantee available for your trip.

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Chicago 5 stars Hotels

See all 801 Hotels in Chicago
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
401 N Wabash Ave, Chicago
5.0 out of 5.0
4.8 out of 5 (750 reviews)
Hide review
The staff was very friendly and upgraded my room when I arrived at the hotel. I had planned on just dropping my bags but was allowed to check in at 9:00am because my room was available. The hotel is high quality; everything one would expect from a Trump location. The rooms are spotless, quiet and ...
  May 22, 2017

$316

$316
The Ritz-Carlton, Chicago
The Ritz-Carlton, Chicago
160 E Pearson Street, Chicago
5.0 out of 5.0
4.6 out of 5 (411 reviews)
Hide review
Wonderful experience! Great room, great bed! Perfect location! The service was wonderful. Great room, great bed, great pillows. This was the perfect place to stay in Chicago. Look forward to to seeing your remodel.
  May 19, 2017

$280

$280
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
120 East Delaware Place, Chicago
5.0 out of 5.0
4.7 out of 5 (168 reviews)
Hide review
Excellent hotel on the Mag-mile. Staff is extremely helpful. Special requests were addressed prior to my arrival. My suite was very spacious and well-equipped.
  Apr 5, 2017

$364

$364
The Peninsula Chicago
The Peninsula Chicago
108 East Superior Street, Chicago
5.0 out of 5.0
4.9 out of 5 (237 reviews)
Hide review
perfect Chicago getaway Incredible friendly and helpful service, first-class room, beautiful pool and ideal location
  May 20, 2017

$399

$399
Waldorf Astoria Chicago
Waldorf Astoria Chicago
11 E. Walton Street, Chicago
5.0 out of 5.0
4.7 out of 5 (219 reviews)
Hide review
Best Hotel in Chicago What can I say? This place is phenomenal! From the rooms (spacious and comfortable) to the service (always top-notch), the Waldorf is simply the best hotel I have ever stayed in during numerous visits to the Windy City.
  May 11, 2017

$355

$355
The Langham, Chicago
The Langham, Chicago
330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.9 out of 5 (250 reviews)
Hide review
Not impressed at all I stayed last year in The Langham NYC and it was superb but The Langham Chicago wasn´t the same story for me, the street was VERY NOISY almost all the time, ambulances, fire trucks, horns, you name it, the room is not "noise proof" at all. Besides I stayed in a Junior Suite and it was very little ...
  May 17, 2017

$344

$344
Park Hyatt - Chicago
Park Hyatt - Chicago
800 N Michigan Ave, Chicago
5.0 out of 5.0
4.8 out of 5 (124 reviews)
Hide review
Great experience, fantastic location, friendly and acccomadating staff.
  May 11, 2017

$292

$292
Map

Chicago Five Star Hotel Information

When you’ve got your heart set on a fancy getaway in the city, dabble in the glamorous side of Chicago, Illinois.

  • Treat yourself to an exclusive hotel with first-rate amenities
  • Receive points and benefits with the Expedia+ program
  • Keep your savings intact and book the best deals around

Sure the deep-dish pizza and Ferris wheel in Chicago are fantastic, but when you’re looking for a luxurious stay in the Windy City, step up your game.

Instead of simply dreaming of designer amenities and royal treatment, make it a reality when you book right here. At Expedia.com, you’ll find an enticing selection of some of the best hotels in Chicago at rates that won’t cost you a fortune. Take a look at our variety of affordable luxury and boutique hotels with fine amenities such as first-class concierge services and views of the city skyline. Some of the top hotels in Chicago boast full-service spas with massage and facial sessions, steam rooms, and saunas, while others present fancy lounges and renowned restaurants. You’ll even come across a number of 5-star places that include rooftop terraces, state-of-the-art fitness centers, and valet parking to further round out your extravagant adventure in Chi-Town.

Continue your glamorous adventure with some retail therapy at the luxury shops along Rush Street, Michigan Avenue, and Oak Street. Shop ’til you drop at these retail strips where you’ll find designer goods and high-end boutiques. Once you’ve spent the day indulging in Chicago’s grand attractions, treat yourself to a three-course dinner at the finest restaurants in town with a view of the city’s skyscrapers. Then to top it all off, return to whichever of the best 5-star hotels in Chicago you chose to keep the lavish times rolling.

Get in touch with the spectacular side of this city in the Land of Lincoln. Chicago offers so much more than street food and amusement rides as it dazzles with marvelous attractions and upscale activities to suit your VIP-stylesojourn. If your idea of a ritzy getaway includes scoring the best seats to the city’s sporting events, book box tickets to cheer on the Cubs at the ballpark or root for the Bears from the 50-yard line of Soldier Field. Alternatively, if you’re looking to show off your sophisticated side, browse through masterpieces at the art galleries in River North and West Loop, and don’t miss a performance at the Civic Opera House. Spoil your ears to the sweet sounds of the Chicago Symphony Orchestra and marvel at the graceful Ballet Chicago.

At Expedia.com we provide you with verified reviews of Chicago hotels. When you read these write-ups, you’ll receive the inside scoop on travelers’ favorite places to stay in town, so that you end up picking a luxurious accommodation that best suits your preferences and needs. You can even use our convenient mobile booking app to browse and make reservations on the fly. Choose the ideal 5-star hotel that matches all your desires to get your opulent Chicago trip started today.

Recently booked Chicago hotels

Park Hyatt - Chicago
5.0 out of 5.0
Last booking: 3 minutes ago