Book Cheap Hotels in Westchester

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Most frequently booked Westchester hotels

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
21.41 km from city centre
Get rates
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
Free WiFi
Restaurant
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Free cancellation
Reserve now, pay when you stay
21.51 km from city centre
The price is CA $138 per night
CA $138
CA $227 total
Oct 27 - Oct 28
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
21.45 km from city centre
The price is CA $271 per night
CA $271
CA $318 total
Oct 19 - Oct 20
includes taxes & fees
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Breakfast included
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
22.12 km from city centre
The price is CA $224 per night
CA $224
CA $263 total
Oct 20 - Oct 21
includes taxes & fees
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pet-friendly
Free WiFi
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
21.47 km from city centre
The price is CA $256 per night
CA $256
CA $300 total
Oct 19 - Oct 20
includes taxes & fees
Stay at this 3-star hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Pet-friendly
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
21.74 km from city centre
The price is CA $374 per night
CA $374
CA $484 total
Oct 30 - Oct 31
includes taxes & fees
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pool
Spa
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
21.57 km from city centre
The price is CA $283 per night
CA $283
CA $332 total
Oct 30 - Oct 31
includes taxes & fees
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the bar in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Free WiFi
Restaurant
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
20.83 km from city centre
Get rates
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pet-friendly
Air conditioning
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL
21.82 km from city centre
The price is CA $184 per night
CA $184
CA $256 total
Oct 22 - Oct 23
includes taxes & fees
Stay at this 4-star family-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Free WiFi
Air conditioning
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See all available properties in Westchester
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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.

Top family friendly Westchester hotel deals

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

2222 Enterprise Drive, Westchester, IL
The price is CA $125 per night from Oct 7 to Oct 8
CA $125
CA $140 total
Oct 7 - Oct 8
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)

Top cheap Westchester hotel deals

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

2222 Enterprise Drive, Westchester, IL
The price is CA $125 per night from Oct 7 to Oct 8
CA $125
CA $140 total
Oct 7 - Oct 8
includes taxes & fees
8.4/10 Very Good! (1,010 reviews)

Top hotels in Westchester for Extended Stay

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

1431 W Taylor St, Chicago, IL
9.6/10 Exceptional! (205 reviews)
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.

Westchester hotels essential information

Accommodation
5,026 hotels
Lowest Price
CA $140
Highest Price
CA $484
Popular hotels
Congress Plaza Hotel, Freehand Chicago, Embassy Suites by Hilton Chicago Downtown River North, Hilton Chicago/Magnificent Mile Suites, Hilton Garden Inn Chicago Downtown/Magnificent Mile, InterContinental Chicago Magnificent Mile by IHG, citizenM Chicago Downtown, The Allegro Royal Sonesta Hotel Chicago Loop, Warwick Allerton - Chicago

Frequently asked questions

What are the top kid-friendly hotels in Westchester?
From well-designed amenities to more room to move, kid-friendly hotels come with features that can help turn a routine family vacation into a fabulous one. These Westchester properties make vacationing with young ones a snap: Holiday Inn Express & Suites Chicago West - OHare Arpt Area will help make your next trip the best one yet. It offers lots of conveniences geared toward families, such as a swimming pool and complimentary breakfast. Otherwise, spend your Westchester break at A beautiful home in quiet Westchester. Take advantage of a king bed, a fireplace and more here.
Where can I find cheap hotels in Westchester?
At Travelocity you'll find really nice hotels in Westchester at great prices. We source incredible prices with our trusted partners, so you have a tempting selection of cheap hotels to choose from. If you can be flexible on dates and location, consider staying at a hotel near Westchester rather than in Westchester. We may find you even better rates, too.
How do I find the best Westchester hotel deals?
Simple! On Travelocity, look through the fantastic offers we've already found in Westchester then use our filters to find a great deal that's perfect for you. Enter your travel dates, select the number of rooms you need, and we'll do the rest. You can get great discounts on flights and car hire, too, when you bundle.
How much does it cost to stay in a hotel in Westchester?
The cheapest hotel in Westchester is CA $140 This price was available within the past 7 days, for stays with a check-in date within the next year. Of course, the price you pay depends on your dates of travel, the length of your stay, and the hotel's location. Prices and availability are subject to change. Additional terms apply.
How many hotels are in Westchester?
There are 5,026 hotels in Westchester on Travelocity.
What are the best hotels in Westchester?
Westchester has so many great hotels to choose from at Travelocity — and it's so easy to find the perfect one. Just choose one of our popular pre-selected hotels with great reviews, or you can refine your search to build your ideal stay. Simply filter hotels based on price or star rating, or select properties with a pool, a hot tub, or a range of other amenities and pick the best place to stay in Westchester for you!
When is the best time to visit Westchester?
If you want the joy of a fun-filled trip in peak season, visit Westchester during April, May and June. If you'd prefer the peace of off-season, book a stay during quieter months, such as November, December and January.
When is the cheapest time to stay in Westchester?
Based on historic data is usually the cheapest month to visit Westchester. However, we have incredible deals all year round, so we're confident you'll find a room in your budget whenever you choose to travel.
Are there any great family-friendly hotels in Westchester?
There are multiple hotels in Westchester that will please the whole family. Do you need adjoining rooms, babysitting services or a swimming pool? We've got you covered. Use our family filter to narrow your search down and use guest reviews to help you pick the perfect place for your next family trip to Westchester. We have plenty of kid-friendly hotels in Westchester to choose from on Travelocity!
Why book a hotel in Westchester through Travelocity?
Because we have the top hotels in Westchester! We want to help you travel more and worry less. That's why we've put the most amazing hotel, car rental, and flight deals in one place. When you search for hotels with us, you know you're getting fantastic prices with no hidden fees and free cancellation on most properties up to 24 hours before your stay. If you become a Travelocity member, you also get exclusive member discounts. Sign up today!
How do I cancel my hotel booking in Westchester on Travelocity?
Canceling your booking with Travelocity is easy. Sign into your account and select My Trips. Here, you will see your cancellation options. We offer free cancellation on many properties.

Recent Westchester hotel reviews by fellow wanderers

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"We enjoyed everything about our stay at the Whitehall."
A verified traveller stayed at The Whitehall Hotel, BW Premier Collection
The Whitehall Hotel, BW Premier Collection

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