Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 321,000 hotels worldwide.

Get the best price available for your trip.

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


Featured Chicago 5 Star Hotels

See all 954 Hotels in Chicago
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

5300 N River Rd, Rosemont
5.0 out of 5.0
4.5 out of 5 (1,804 reviews)
Great get away! Great Hotel!A last minute date night turned into a nice mini get away thanks to the in-laws watching the 2 year old! The hotel was very clean, staff was great and we had a great dinner at the attached Capital Grill. I would highly recommend this hotel to all my friends and family!
  Dec 15, 2017

$129

$129
Omni Chicago Suites - Magnificent Mile

Omni Chicago Suites - Magnificent Mile

676 N Michigan Ave, Chicago
5.0 out of 5.0
4.4 out of 5 (2,828 reviews)
Perfect Hotel for familiesHotel provided my children with a little welcome gift with activities for them and in the evening, chocolate chip cookies and milk. I will always stay here with my children when downtown.
  Dec 13, 2017

$134

$134
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

127 West Huron, at LaSalle, Chicago
5.0 out of 5.0
4.4 out of 5 (2,286 reviews)
Hotel with a beautiful view Beautiful hotel with a beautiful view. I put in my comment section when I booked this hotel to get a view with the price point I was paying. If you're looking for a quite room make sure you let the hotel staff know so they can accomadate your stay because you could definitely hear bar going all day/night ...
  Dec 13, 2017

$98

$98
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago
5.0 out of 5.0
4.2 out of 5 (2,103 reviews)
Right on the Mag Mile, Close to everythingMy girlfriend and I stayed here for two night to celebrate our one year anniversary, we couldn't have picked a better place. The hotel was very upscale, everything was absolutely perfect. The staff are amazingly helpful and even more friendly. We had no issues whatsoever with our stay. The restaurant ...
  Dec 12, 2017

$99

$99
Loews Chicago Hotel

Loews Chicago Hotel

455 North Park Drive, Chicago
5.0 out of 5.0
4.7 out of 5 (981 reviews)
Great Concierge helpWith a 2 day whirl wind trip with 3 teens, I could not have done it without the help from the hotel concierge! We went to a music concert, saw the bean, museum, aquarium, broadway play, tilt, 360 skybox, ate Chicago deep dish, sugar factory, Mile shops and in just 2 days! The room service night attendant ...
  Dec 15, 2017

$149

$149
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.9 out of 5 (679 reviews)
Modern hotel in great location Usually stay at the Trump Tower but got a very good discounted rate at the Langham. Love the location. Close to walk to everything. Love the spacious room and bathroom. The bathtub is huge!!! Love the bar and view of river. The staff bends over backwards to accommodate. Would’ve given all 5 stars ...
  Dec 13, 2017

$305

$305
The James Chicago-Magnificent Mile

The James Chicago-Magnificent Mile

55 East Ontario Street, Chicago
5.0 out of 5.0
4.5 out of 5 (2,128 reviews)
Perfect location very nice lobby for relaxing I am happy
  Dec 15, 2017

$103

$103
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago
5.0 out of 5.0
4.4 out of 5 (3,388 reviews)
Spent two nights at the hotel. Was able to walk to restaurants & shopping. The staff was wonderful!
  Dec 15, 2017

$119

$119
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

85 East Wacker Drive, Chicago
5.0 out of 5.0
4.6 out of 5 (784 reviews)
Check inAt check in the beds are smaller then we though from the pictures. Planned to have are daughters with us we will have to try and upgrade or rent another room. We are some what disappeared.
  Dec 14, 2017

$109

$109
Kimpton Gray Hotel

Kimpton Gray Hotel

122 West Monroe Street, Chicago
5.0 out of 5.0
4.7 out of 5 (372 reviews)
nice hotel, great location, friendly staffgirls weekend away, close to the christkindle market, plenty of restaurants and shopping nearby. staff friendly and helpful
  Dec 12, 2017

$104

$104
Map

Ready for an incredible adventure? Add even more pleasure on your next trip to Chicago by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Chicago so popular in the last year. Come see what all the fuss is about. Furthermore, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. Book one of Expedia's luxurious 5-star hotels in Chicago and get ready to be pampered like never before. Don't wait any longer!

5-Star Hotels in Chicago

Don't be afraid to be pampered during your trip, along with the best conditions. Spa treatments, delicious meals, and one-on-one attention are all at your fingertips. We have a tremendous number of hotels in the region, and all of them provide awesome amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. How do you want to relax? A reflexology treatment that will leave you feeling great? 24-hour room service, so you can order that chocolate soufflé© in the wee hours of the morning? A full-body massage to help your cares fall away? Don't want to take our word for it? Then explore the 12,572 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? You're in luck. You'll find all kinds of activities in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals -- they'll be happy to sit down for a pint or a cuppa.

Your Getaway Starts Today

The results are in, and Chicago 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Don't put off your dream vacation any longer -- this is a great time to find 5-star hotel deals in @region! Decide on one of the 5-star hotels in Chicago today and relax in luxe surroundings when you're ready.

Recently booked 5 Star Hotels in Chicago

La Quinta Inn & Suites Chicago Downtown
3.0 out of 5.0
Last booking: 1 minute ago
Chicago Marriott at Medical District/UIC
4.0 out of 5.0
Last booking: 7 minutes ago
Hilton Chicago O'Hare Airport
4.5 out of 5.0
Last booking: 7 minutes ago
The Ritz-Carlton, Chicago
5.0 out of 5.0
Last booking: 8 minutes ago
Holiday Inn Express Chicago-Magnificent Mile
3.0 out of 5.0
Last booking: 9 minutes ago
Best Western At O'Hare
3.5 out of 5.0
Last booking: 11 minutes ago
Sleep Inn Lansing
2.5 out of 5.0
Last booking: 13 minutes ago
Holiday Inn Express & Suites Chicago North Shore - Niles
3.0 out of 5.0
Last booking: 13 minutes ago
Hampton Inn & Suites Chicago-Libertyville
3.0 out of 5.0
Last booking: 13 minutes ago