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

Search 400 airlines and 321,000 hotels worldwide.

Get the guaranteed best price available for your trip.

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


Featured Chicago 5 Star Hotels

See all 937 Hotels in Chicago
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

5300 N River Rd, Rosemont
5.0 out of 5.0
4.4 out of 5 (67 reviews)
Nice stay !Staff was extremely pleasant and accommodating. Room was clean and comfortable.
  Nov 20, 2017

$129

$129
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 (17 reviews)
Great stay! Cant wait to stay again! Staff was excellent and hote was so beautiful! Rooms were clean comfortable and had an awesome view!!!! Best hotel for the money, we will def be back
  Aug 2, 2017

$96

$96
The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

909 North Michigan Ave, Chicago
5.0 out of 5.0
3.9 out of 5 (68 reviews)
Nice spot on Mag MileThe rooms smelled like a dead mouse or rat had died in the heat vents
  Nov 22, 2017

$117

$117
Loews Chicago Hotel

Loews Chicago Hotel

455 North Park Drive, Chicago
5.0 out of 5.0
5.0 out of 5 (8 reviews)
Perfect location. Room very well arranged great view of the lake
  Dec 11, 2017

$149

$149
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.8 out of 5 (4 reviews)
Luxury HotelWe loved our stay at the Langham-very clean, staff is excellent. Was a 5 star experience.
  Jul 5, 2017

$278

$278
The James Chicago-Magnificent Mile

The James Chicago-Magnificent Mile

55 East Ontario Street, Chicago
5.0 out of 5.0
4.4 out of 5 (72 reviews)
Repeat Visitor!This is now my "go to" hotel for Chicago visits. Great location and the hotel staff is fantastic. I think the deluxe room is worth paying for and the amenities are terrific.
  Aug 21, 2017

$82

$82
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago
5.0 out of 5.0
4.3 out of 5 (73 reviews)
Great Location and ValueWe arrived well ahead of check-in time, but our room was ready, so we were able to walk around the city without having to carry our luggage - a great start to our visit. The room was spacious and spotlessly clean. The hotel is in a great location, 2 blocks south of the river and a short walk north ...
  Jul 10, 2017

$127

$127
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

85 East Wacker Drive, Chicago
5.0 out of 5.0
4.3 out of 5 (7 reviews)
Great locationGreat location. Close to magnificent mile, Willis tower and millennium park. Nice hotel room.
  Jul 15, 2017

$93

$93
Kimpton Gray Hotel

Kimpton Gray Hotel

122 West Monroe Street, Chicago
5.0 out of 5.0
4.8 out of 5 (5 reviews)
I absolutely loved my stay at the Kimpton Gray Hotel and would definitely recommend staying here. The location downtown was perfect and close to everything that I wanted to see and experience during my stay. My room was very clean and the guestroom design was fresh and modern.
  Dec 5, 2017

$139

$139
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago
5.0 out of 5.0
4.7 out of 5 (18 reviews)
Outstanding!Neither my wife or I have one nagitive thing to say about Trump International in Chicag. We’ve stayed in many hotels around the country and this was by far the best! Excellent staff!
  Nov 23, 2017

$276

$276
Map

Recently booked Chicago hotels

American Inn & Suites
2.5 out of 5.0
Last booking: 1 minute ago
Hyatt Place Chicago/O'Hare Airport
3.5 out of 5.0
Last booking: 1 minute ago
Hyatt Regency Chicago
4.0 out of 5.0
Last booking: 1 minute ago
Candlewood Suites Aurora-Naperville
3.0 out of 5.0
Last booking: 4 minutes ago
River Hotel
4.0 out of 5.0
Last booking: 4 minutes ago
La Quinta Inn & Suites Chicago Downtown
3.5 out of 5.0
Last booking: 5 minutes ago
Ivy Boutique Hotel
5.0 out of 5.0
Last booking: 6 minutes ago
Country Inn & Suites By Carlson, O'Hare South
3.5 out of 5.0
Last booking: 9 minutes ago
Four Points by Sheraton Chicago O'Hare Airport
3.5 out of 5.0
Last booking: 11 minutes ago

About Chicago 5 stars Star Hotels

Book your travels from the selection of 5 stars star hotels in Chicago, Illinois.

Download Our Mobile App

Make booking your next reservation quick & easy. Download the Travelocity mobile app now for even more of the best deals and featured offers. Wander Wisely!