Search Chalets in Westchester from CA $172

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Westchester chalets

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,493 reviews)
"Great place to stay "
United States
Mark
The price is CA $251
CA $345 total
includes taxes & fees
May 26 - May 27
Sable at Navy Pier Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (3,707 reviews)
"Amazing hotel and staff!"
United States
erin
The price is CA $257
CA $345 total
includes taxes & fees
May 25 - May 26
LondonHouse Chicago, Curio Collection by Hilton

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,431 reviews)
"We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff. "
United States
Cynthia
The price is CA $202
CA $281 total
includes taxes & fees
May 25 - May 26
Palmer House a Hilton Hotel

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, (1,002 reviews)
"The room has clean & quiet. Nothing special. Did not try the breakfast. Decent stay. Nothing special. "
United States
GARY
The price is CA $163
CA $182 total
includes taxes & fees
May 10 - May 11
Four Points by Sheraton Chicago Westchester/Oak Brook

Congress Plaza Hotel

Congress Plaza Hotel
3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (10,184 reviews)
"Great stay"
United States
Matthew
The price is CA $182
CA $216 total
includes taxes & fees
May 9 - May 10
Congress Plaza Hotel

Hilton Chicago

Hilton Chicago
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2,780 reviews)
"Clean room and great location "
United States
Diana
The price is CA $217
CA $298 total
includes taxes & fees
May 25 - May 26
Hilton Chicago

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (2,257 reviews)
"Close to many attractions and shopping and nice unique hotel"
United States
Brittany
The price is CA $163
CA $235 total
includes taxes & fees
May 25 - May 26
Silversmith Hotel Chicago Downtown

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (1,423 reviews)
"Great stay, love the surrounding area. Rooms a bit small but overall a great stay. "
United States
Eric
The price is CA $183
CA $218 total
includes taxes & fees
May 10 - May 11
The Chicago Hotel Collection Ambassador Gold Coast

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (3,231 reviews)
"The design of the property and location is great!"
United States
Fedna
The price is CA $217
CA $258 total
includes taxes & fees
May 26 - May 27
Aloft Chicago Mag Mile

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,150 reviews)
"A great option to stay in the city! Nice hotel and friendly staff."
United States
Nicole
The price is CA $263
CA $361 total
includes taxes & fees
May 26 - May 27
Fairmont Chicago at Millennium Park

The Drake

The Drake
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (1,451 reviews)
"Loved staying at this hotel. "
United States
Geraldine
The price is CA $249
CA $296 total
includes taxes & fees
May 26 - May 27
The Drake

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,985 reviews)
"Had a great stay-5 stars of 5"
United States
donald
The price is CA $179
CA $213 total
includes taxes & fees
May 26 - May 27
Hilton Garden Inn Chicago Downtown South Loop

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago
3.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,396 reviews)
"Very friendly staff, great location."
Canada
Annabel
The price is CA $228
CA $309 total
includes taxes & fees
May 25 - May 26
Sports Illustrated Resorts Chicago

Eurostars Magnificent Mile

Eurostars Magnificent Mile
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (3,514 reviews)
"The hotel was phenomenally clean, the staff was nice !"
United States
Rochelle
The price is CA $197
CA $234 total
includes taxes & fees
May 10 - May 11
Eurostars Magnificent Mile

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites
3.5 star property
Downtown Chicago
9.0 out of 10, Wonderful, (4,269 reviews)
"Great place to stay , good location"
United States
Judith Daniella
The price is CA $185
CA $220 total
includes taxes & fees
May 25 - May 26
Hilton Chicago/Magnificent Mile Suites

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (4,086 reviews)
"Great hotel in an amazing location!"
United States
Samer
The price is CA $204
CA $281 total
includes taxes & fees
May 27 - May 28
Hotel Riu Plaza Chicago

Arlo Chicago

Arlo Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2,114 reviews)
"Great breakfast and staff. "
United States
Kelly
The price is CA $183
CA $259 total
includes taxes & fees
May 25 - May 26
Arlo Chicago

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1,830 reviews)
"We enjoy our stay."
United States
Nuria
The price is CA $176
CA $210 total
includes taxes & fees
May 10 - May 11
The Wade

The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile
4.0 star property
Downtown Chicago
7.8 out of 10, Good, (1,382 reviews)
"The bar was well stocked and the bar staff was great!!"
United States
Daynese
The price is CA $166
CA $197 total
includes taxes & fees
May 11 - May 12
The Chicago Hotel Collection - Magnificent Mile

FOUND Hotel Chicago River North

FOUND Hotel Chicago River North
2.0 star property
Downtown Chicago
8.4 out of 10, Very good, (594 reviews)
"Great stay!"
United States
Vanessa
The price is CA $146
CA $172 total
includes taxes & fees
May 10 - May 11
FOUND Hotel Chicago River North
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Westchester Hotel Reviews

Find out more about Westchester

Westchester Chalets information

Number of reviews
54,279
Accommodation
0 Chalets
Lowest Price
CA $172
Highest Price
CA $361

Explore a world of travel with Expedia