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Choose from 5129 Westchester Hotel Deals
Congress Plaza Hotel
"Room was super clean. Comfortable bed. Shower took quite awhile to warm up. Overall great location and will stay again."
Reviewed on Jun 22, 2026
Hilton Chicago/Magnificent Mile Suites
"Cleaneage rooms. Great location. Lovely staff"
Reviewed on Jun 21, 2026
The Chicago Hotel Collection - Magnificent Mile
"The hotel was in a great location, and the staff were friendly and welcoming. My only complaint was that the hallway smelled like cigarettes and damp carpet. Overall, it was a pleasant stay, but the hallway and elevator odor could definitely be improved."
Reviewed on Jun 21, 2026
Hyatt Regency O'Hare Chicago
"Clean room, very friendly staff, we ate at one of the restaurants and the food and drinks were great. I will definitely recommend and go back here again."
Reviewed on Jun 21, 2026
The Chicago Hotel Collection Ambassador Gold Coast
"The lobby and first floor looked nice, and the staff was friendly, but that’s where the positives ended. This was supposed to be a four-star hotel, yet it felt more like a four-star motel. The bathrooms were not very clean and had an awkward layout. There was no daily housekeeping service, and the ..."
Reviewed on Jun 21, 2026
Hilton Chicago O'Hare Airport
"Such a relaxing way to fly out of O'hare on an early am flight. Dinner at the Gaslight was delicious."
Reviewed on Jun 21, 2026
Freehand Chicago
"Easy check in, clean room, helpful staff, great location."
Reviewed on Jun 22, 2026
Travelodge by Wyndham Downtown Chicago
"Basic but a great location"
Reviewed on Jun 22, 2026
Palmer House a Hilton Hotel
"Prepaid parking through Expedia not honored at the hotel. Staff completely unhelpful in sorting this issue out. Forced to double pay for parking. Rooms dated with older furnishings. Beds old. Plumbing drained poorly. Location nice but otherwise I would not recommend."
Reviewed on Jun 22, 2026
Omni Chicago Hotel
"Fabulous"
Reviewed on Jun 21, 2026
Hotel Riu Plaza Chicago
"Beautiful hotel, perfect location! Loved everything about this hotel. Breakfast was great. But they really want you out of the restaurant right at the closing time so give yourself time in the morning for breakfast"
Reviewed on Jun 21, 2026
InterContinental Chicago Magnificent Mile by IHG
"Great customer service. Pool was very unique!"
Reviewed on Jun 21, 2026
Find cheap hotels in Westchester
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For you, intrepid voyager, Hotwire has a large selection of the best hotels in Westchester.
Choosing the right hotel in Illinois has everything to do with the way you want your trip to go. If you’ve scribbled a few obscure destinations on your itinerary, you probably already have a good sense of how your getaway is taking shape. Lean into that by booking one of Westchester’s 5,129 hotels. Choose the one that best catches your trip’s tourist drift.
If you’re traveling during the week for business, Hotwire can score you a luxury hotel for as low as $146. In town for pleasure? Hotwire still has you covered. If you’re in the mood for a quick last-minute weekend getaway or spa retreat, you can get great Westchester hotel deals at the last minute.
While traveling, where you stay plays a major role in your overall vacation enjoyment. Choosing the right hotel is just as important as making sure you book the right flight and car rental. If you’re traveling with family or friends, you may need to book a hotel with connecting rooms. If you enjoy an elegant and relaxing hotel ambiance, opt for one of Hotwire’s luxury hotels in Westchester. No matter your reason for visiting Westchester, with Hotwire’s large selection of hotels in the area, you’re sure to book a hotel that meets all your accommodation needs.
Frequently Asked Questions About Westchester hotels
Where can I find the best last-minute travel deals?
If you’re traveling in the spirit of spontaneity, you’ll love the idea of leaving your exact hotel choice up to chance. With Hotwire Hot Rates, you can unlock great deals on your next flight, hotel, or car rental. Just plug in your general preferences and let Hotwire choose last-minute hotel deals in Westchester for as low as $146.
How many hotels are there in Westchester?
With over 5,129 hotels in Westchester, you’re sure to find one that best matches your travel mood. When you book with Hotwire, you can score a stellar home away from home for as low as $146.
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Finding a cheap car rental deal in Westchester is as easy as scoring cheap hotels in Westchester. Hotwire partners with top-of-the-line car rental companies to bring you a large selection of affordable options. Whether you’re in need of a large SUV for the entire family or a more compact but stylish vehicle, Hotwire has you covered. You can unlock great car rental deals if you book a Hotwire Hot Rate at the last minute.
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