Book Cheap Hotels in Westchester

Check hotel availability in Westchester

Tonight

Nov 14 - Nov 15

Tomorrow night

Nov 15 - Nov 16

Next weekend

Nov 20 - Nov 22

Most frequently booked Westchester hotels

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free cancellation

Reserve now, pay when you stay

21.41 km from city centre

CA $166

CA $197 total

Nov 23 - Nov 24

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). 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

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free cancellation

Reserve now, pay when you stay

21.8 km from city centre

CA $165

CA $197 total

Dec 1 - Dec 2

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). 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

River Hotel

75 East Wacker Drive Chicago IL

Free cancellation

Reserve now, pay when you stay

21.53 km from city centre

CA $151

CA $180 total

Dec 10 - Dec 11

includes taxes & fees

Book a stay at this business-friendly 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 Chicago Riverwalk and Michigan Avenue are located nearby.

Pet-friendly

Free WiFi

The Wade

644 N Lake Shore Dr Chicago IL

Free cancellation

Reserve now, pay when you stay

22.51 km from city centre

CA $170

CA $202 total

Nov 22 - Nov 23

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Navy Pier are located nearby.

Pool

Pet-friendly

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Free cancellation

Reserve now, pay when you stay

21.96 km from city centre

CA $149

CA $177 total

Nov 23 - Nov 24

includes taxes & fees

Book a stay at this boutique 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 Michigan Avenue and Chicago Riverwalk are located nearby.

Pet-friendly

Free WiFi

Hilton Chicago

720 S Michigan Ave Chicago IL

Free cancellation

Reserve now, pay when you stay

21.34 km from city centre

CA $193

CA $271 total

Nov 23 - Nov 24

includes taxes & fees

Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

Pool

Hot tub

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

172 W Adams St Chicago IL

Free cancellation

Reserve now, pay when you stay

20.77 km from city centre

CA $198

CA $236 total

Nov 23 - Nov 24

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Pet-friendly

Free WiFi

The Royal Sonesta Chicago Downtown

71 E Wacker Dr Chicago IL

Free cancellation

Reserve now, pay when you stay

21.52 km from city centre

CA $170

CA $247 total

Dec 14 - Dec 15

includes taxes & fees

Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.

Pet-friendly

Free WiFi

Fairmont Chicago at Millennium Park

200 North Columbus Drive Chicago IL

Free cancellation

Reserve now, pay when you stay

21.87 km from city centre

CA $284

CA $388 total

Dec 6 - Dec 7

includes taxes & fees

Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.

Spa

Pet-friendly

Don't see what you're looking for?

See all available properties in Westchester

View all properties

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

2222 Enterprise Drive Westchester IL

CA $156

CA $175 total

Nov 25 - Nov 26

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

Top cheap Westchester hotel deals

Four Points by Sheraton Chicago Westchester/Oak Brook

2222 Enterprise Drive Westchester IL

CA $156

CA $175 total

Nov 25 - Nov 26

includes taxes & fees

8.6/10 Excellent! (1,003 reviews)

Top hotels in Westchester for Extended Stay

The Neighborhood Hotel-Little Italy

1431 W Taylor St Chicago IL

9.6/10 Exceptional! (378 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	4,973 hotels
Lowest Price	CA $175
Highest Price	CA $388
Popular hotels	Congress Plaza Hotel, The Chicago Hotel Collection Ambassador Gold Coast, River Hotel, The Wade, The Chicago Hotel Collection - Magnificent Mile, Hilton Chicago, THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel, The Royal Sonesta Chicago Downtown, Fairmont Chicago at Millennium Park

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 $175 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 4,973 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.