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

Check prices on hotels in Chicago

Best deal Best deal Oct 5 - Oct 7
Tonight Tonight Sep 18 - Sep 19
This weekend This weekend Sep 21 - Sep 23
Next weekend Next weekend Sep 28 - Sep 30

Featured Chicago 5 Star Hotels

See all 1,166 Properties in Chicago
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago
  • Free Cancellation
  • Reserve now, pay when you stay
5.0 out of 5.0
 
 
4.8 out of 5 (2,011 reviews)
OMG - This hotel is amazingI don't like Donald Trump politics very much, but OMG he's good at hotels. This hotel is amazing. Beautiful interiors, spectacular spa and locker rooms, lovely big pool with fabulous views. It's in the best location in the whole of Chicago. Everywhere was spotless. Staff are obviously trained within ...
Sep 4, 2018
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
  • Free Cancellation
  • Reserve now, pay when you stay
5.0 out of 5.0
 
 
4.9 out of 5 (942 reviews)
Fantastic hotel Great facilities,especially the pool. Good location near to some good bars & restaurants!
Sep 9, 2018

$376 per night for 2 guests

The Langham, Chicago$376
The Peninsula Chicago

The Peninsula Chicago

108 East Superior Street, Chicago
  • Free Cancellation
  • Reserve now, pay when you stay
5.0 out of 5.0
 
 
4.9 out of 5 (902 reviews)
The rooms are beautiful and hotel staff very nice. The new roof top bar is great.
Sep 16, 2018

$425 per night for 2 guests

The Peninsula Chicago$425
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

160 E Pearson Street, Chicago
  • Free Cancellation
  • Reserve now, pay when you stay
5.0 out of 5.0
 
 
4.6 out of 5 (1,217 reviews)
Overcoimg job action which reduced hotel staffing during our stay.
Sep 11, 2018

$329 per night for 2 guests

The Ritz-Carlton, Chicago$329
Waldorf Astoria Chicago

Waldorf Astoria Chicago

11 E. Walton Street, Chicago
    5.0 out of 5.0
     
     
    4.8 out of 5 (807 reviews)
    The best hotel and service I have ever had. If you want a top notch experience stay here. You will not regret it.
    Sep 11, 2018

    $350 per night for 2 guests

    Waldorf Astoria Chicago$350
    Four Seasons Hotel Chicago

    Four Seasons Hotel Chicago

    120 East Delaware Place, Chicago
    • Free Cancellation
    • Reserve now, pay when you stay
    5.0 out of 5.0
     
     
    4.7 out of 5 (610 reviews)
    tv cable selection and movies need work and very slow, no Netflix no movies
    Sep 4, 2018

    $450 per night for 2 guests

    Four Seasons Hotel Chicago$450
    Park Hyatt - Chicago

    Park Hyatt - Chicago

    800 N Michigan Ave, Chicago
    • Free Cancellation
    • Reserve now, pay when you stay
    5.0 out of 5.0
     
     
    4.7 out of 5 (464 reviews)
    Great hotel in a great location Our room was lovely with a massive bath with sliding doors onto the bedroom to allow a view from the tub! Housekeeping was excellent and the toiletries had a lovely aroma. Fitness facilities were great with a good length pool and gym with plentiful treadmills - bottles of water and in-gym towels ...
    Jul 20, 2018

    $274 per night for 2 guests

    Park Hyatt - Chicago$274
    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

    Holiday Inn Chicago Nw Crystal Lk Conv Ctr
    3.0 out of 5.0
    Last booking: 1 minute ago
    Extended Stay America Chicago - Skokie
    2.5 out of 5.0
    Last booking: 5 minutes ago
    Hilton Orrington / Evanston
    4.0 out of 5.0
    Last booking: 14 minutes ago
    Sheraton Grand Chicago
    4.0 out of 5.0
    Last booking: 15 minutes ago
    Holiday Inn Express & Suites Chicago North Shore - Niles
    2.5 out of 5.0
    Last booking: 17 minutes ago
    Kimpton Gray Hotel
    4.5 out of 5.0
    Last booking: 25 minutes ago
    Crowne Plaza Hotel Chicago O'Hare
    3.5 out of 5.0
    Last booking: 34 minutes ago
    Indian Lakes Hotel
    3.5 out of 5.0
    Last booking: 36 minutes ago
    Motel 6 Chicago N Central-Arlington Hgt
    2.0 out of 5.0
    Last booking: 37 minutes ago