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Check availability on Westchester Hotels with Connecting Rooms

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Westchester Hotels with Connecting Rooms

Breakfast and dinner served
Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

3.0 star property
Westchester
8.6 out of 10, Excellent, (1004)
"Nice hotel "
United States
Maciej
The price is 2.663.471 ₫
2.982.554 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Four Points by Sheraton Chicago Westchester/Oak Brook
Lobby
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2098)
"Would stay again. "
United States
Montroy
The price is 2.602.619 ₫
3.860.118 ₫ total
includes taxes & fees
3 Jan - 4 Jan 2026
Silversmith Hotel Chicago Downtown
Reception
Swissotel - Chicago

Swissotel - Chicago

4.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (2989)
"Great stay"
Canada
Lorrington Ashford
The price is 2.495.018 ₫
3.702.949 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Swissotel - Chicago
Cocktail bar
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2944)
"Great location and great staff!!"
United States
lynne
The price is 2.373.390 ₫
2.786.121 ₫ total
includes taxes & fees
1 Jan - 2 Jan 2026
Aloft Chicago Mag Mile
Lobby sitting area
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4.0 star property
Downtown Chicago
8.4 out of 10, Very good, (2994)
"Enjoyed this hotel stay. "
United States
Kimberly
The price is 1.793.228 ₫
2.879.186 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Warwick Allerton - Chicago
Exterior
The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3105)
"Very nice staff, beautiful hotel and a clean room"
United States
Tara
The price is 3.006.294 ₫
4.372.962 ₫ total
includes taxes & fees
2 Jan - 3 Jan 2026
The Royal Sonesta Chicago Downtown
Bar (on property)
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3.0 star property
Downtown Chicago
8.4 out of 10, Very good, (4215)
"Great location. "
United States
Rodger
The price is 2.194.067 ₫
2.575.615 ₫ total
includes taxes & fees
22 Dec - 23 Dec
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Cocktail bar
Claridge House Chicago, Tapestry Collection by Hilton

Claridge House Chicago, Tapestry Collection by Hilton

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1472)
"Loved this hotel, great location, pet friendly."
United States
Tracy
The price is 1.816.434 ₫
2.906.301 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Claridge House Chicago, Tapestry Collection by Hilton
Ballroom
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3432)
"Great hotel located in nice area."
United States
Robert
The price is 2.768.110 ₫
3.249.485 ₫ total
includes taxes & fees
14 Dec - 15 Dec
Hilton Chicago/Magnificent Mile Suites
Bar (on property)
voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3433)
"Great hotel"
United States
Clara
The price is 2.721.694 ₫
3.194.996 ₫ total
includes taxes & fees
24 Dec - 25 Dec
voco Chicago Downtown - Riverwalk by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Westchester Hotel Reviews

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