Westchester Holidays from £1,016

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Your Westchester Holiday

A great way to experience this vibrant city is with a tailor-made Westchester holiday package. Stay in the neighbourhood of Wicker Park, which is good for nightlife, bars and pubs and cafes or choose someplace else — our package deals are all about you. If taking in sights is part of the programme during your trip to Westchester, look around well-known attractions like Brookfield Zoo, Oakbrook Centre Mall and Frank Lloyd Wright Historic District. Don't put off your visit to this destination any longer. The ultimate Westchester holiday is just a few clicks away with Expedia.

The Latest Westchester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
13 Jul - 17 Jul
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (3,511 reviews)
Tuve un late Checkin. Fue notificado. Me dieron una habitación diferente a la reservada. Al día siguiente tuvimos que cambiarnos, perdí lo que había comprado de comida pues no tenía donde guardarlo al dejar la habitación. Me dijeron que me darían un upgrade y me dieron una habitación exactamente como la había reservado inicialmente, además les pedí una cobija adicional Y más amenities y no las dejaron en la nueva habitación. No hubo ninguna compensación por el mal rato. El personal de front desk solo se disculpó amablemente. Esto no debería ocurrir. El hotel tiene una locación estupenda, el roof top vale la pena, el brunch nada espectacular. Pero agradable servicio.

Reviewed on 21 May 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on 16 Mar 2024

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,902 reviews)
Beautiful room. Staff was responsive to messaging. Bed was hard. Not much with coffee or creamer. Need a safe in room.

Reviewed on 24 May 2024

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Very nice, clean, large rooms. Well-appointed. Hotel lobby very welcoming. Looked like a lovely outdoor dining patio, though I didn’t eat there.

Reviewed on 22 May 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
13 Jul - 17 Jul
found 9 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,190 reviews)
Great view and environment

Reviewed on 23 May 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
10 Aug - 17 Aug
found 23 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Enjoyed the property and roof top pool

Reviewed on 21 May 2024

Westchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
16,700
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Brookfield Zoo, Rosemont Theatre and Parkway Bank Park Entertainment District

Our pick of the best Westchester Hotel Deals

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this family-friendly hotel in Chicago. Enjoy a 24-hour fitness centre, valet parking (surcharge) and in-room massages. Our guests praise the helpful ...
7.6/10 Good! (2,612 reviews)
"The stay was enjoyable! Conveniently to downtown Chicago, clean and quiet each night we enjoyed the city! Will stay again definitely."

Reviewed on 24 May 2024

Warwick Allerton - Chicago
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.6/10 Good! (6,797 reviews)
"Great historical hotel which is undergoing massive updates at the time we visited. Whole wings were being done. Our room smelled of fresh paint. Large gaps under doors made privacy and noise an issue between guests. However, the panoramic view of the lakefront from the 10th was breathtaking and location ..."

Reviewed on 24 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free Wi-Fi, room service and a fitness centre. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (2,887 reviews)
"Appreciated the easy of self serve check in and checkout. Did not have to stand in line. Only complaint is that the wait time for elevators is too long. Number iof elevators do not support number of guests"

Reviewed on 22 May 2024

River Hotel
See all 4,634 properties in Westchester
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Westchester holiday with Expedia?
Expedia has you covered for all aspects of your Westchester holiday. You’ll always get the best prices around, but when you bundle your accommodation, flights and/or car hire into a holiday package, you’ll get even more savings. Want to truly make the most of your stay? Add some activities and tours to your package. We offer flexible cancellation policies on almost all bookings, so there’s no need to worry if you have to change your plans. Head over to our Customer Service Portal link to discover more.
When is the best time of year to holiday in Westchester?
If you want to experience the excitement of Westchester during the high season, lock in your adventure for April, May and June. November, December and January are usually the quietest months of the year. With average daytime temperatures of -3ºC, January is the coolest month in Westchester. The warmest month is July, when you can experience average temperatures of 23ºC during the day. Whatever the weather, you’ll find plenty to keep you occupied here.
What is the top hotel for my holiday in Westchester?
LondonHouse Chicago, Curio Collection by Hilton is the perfect base for an epic getaway in Westchester, offering all the conveniences you need.
How do I get a cheap holiday to Westchester?
Our Westchester holidays mean plenty of savings for the savvy wanderer. For the best deals, simply combine your flights, hotels and hire cars. But bargain prices are only the start of your next epic adventure. Book with Expedia and you’ll have more than 400 airlines and 321,000 properties worldwide to select from. No matter your style or budget, there’s a holiday here just for you. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Westchester holiday?
Make sure your next holiday in Westchester is a memorable one by taking in its major attractions. Brookfield Zoo, SeatGeek Stadium, Donald E. Stephens Convention Centre and Oakbrook Centre Mall are just a few of the things you must see while you’re in the area.
What is the best area to stay in when on holiday in Westchester?
If you’re interested in visiting Fresh Meadow Golf Club, save yourself the hassle of commuting and find somewhere to stay close by. It’s one of the best attractions in Westchester.
Do I need a visa for my Westchester holiday?
Official government websites have all the information you need on visa requirements, application procedures and any supporting documentation. Your nationality and reason for travelling, whether it be for tourism or business, will determine if you’ll need a visa for Westchester. Also check that your passport is up to date and has at least six months validity remaining after your return date. Finalise all your travel planning well ahead of time to avoid any last-minute surprises.
What should I wear on my Westchester holiday?
Consider the activities planned during your Westchester holiday and take versatile pieces that you can mix and match. For fashion inspiration or even information on dress codes, look up a few style blogs or social media accounts. Daytime temperatures during January, Westchester’s coolest month, average -3ºC. July marks this destination’s warmest month when the average reaches 23ºC. Our suggestion? Take the guesswork out of packing and check the local weather forecast.
What does an Expedia Westchester holiday include?
Flights, hire cars and hotels — we have them covered. With Expedia, you can shape your Westchester travel package the way you want. All you have to do is work out exactly what you need. Once you’ve made your booking, why not add extras like tours and activities? The more you bundle, the bigger the savings! Expedia features all kinds of properties, with the most sought after in Westchester including private holiday homes and hotels. With Expedia, you can expect the freedom and flexibility to personalise your holiday however you want.
Does Expedia offer Book Now, Pay Later Westchester holidays?
Your bank balance shouldn’t stop you from taking a holiday, so Expedia has devised a solution to help. Thanks to our partnership with online lender Klarna, it’s easier than ever to book a fantastic getaway without hurting your hip pocket. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying across multiple transactions sounds best for you, Klarna offers just that! Paying in several transactions will make that dream holiday possible.
  • No-deposit holidays: When you spot an awesome deal but your budget doesn’t quite go that far, Klarna’s no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a Westchester Expedia holiday?
Expedia offers access to more than 400 partner airlines globally, so you sure can! Simply pick your favourite carrier and put together your ideal Westchester trip.

Discover the most popular places to visit in Westchester

Image for Wrigley Field

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Image for Six Flags Great America

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America
Image for McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place

Unmissable things to do in Westchester

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

£182
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
See all activities in Westchester

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.