Westchester Holidays from £1,096

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Your Westchester Holiday

A great way to experience this lively city is with a tailor-made Westchester holiday package. Stay in the neighbourhood of Wicker Park, which is great for nightlife, bars and pubs and cafes or go someplace else — our package deals are all about you. A trip to Westchester is a great opportunity to sightsee. Be sure to visit renowned attractions like Brookfield Zoo, Oakbrook Centre Mall and Frank Lloyd Wright Historic District. Don't put off your visit to this city any longer. The perfect Westchester holiday is only a few clicks away with Expedia.

Top Westchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
25 Aug - 29 Aug
found 12 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
Hotel staff and room were awesome..bed very comfortable. Coffee shop was great had great fast breakfast options. Had Miss Rickie's one day was really great food. Only complaint would be the rooftop bar evening clientele...did not feel comfortable and they were loud and raucous.

Reviewed on 8 Jul 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
25 Aug - 29 Aug
found 12 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on 12 Jul 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
23 Aug - 30 Aug
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Always love our stay at The Peninsula!

Reviewed on 29 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
25 Aug - 29 Aug
found 12 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
I didn’t like the staff insinuating that I couldn’t afford a bottle of Dom. I didn’t like the 3 calls to my room to make sure I understood what the price was. I didn’t like how Brandy told me the reason for doubting my ability to pay for a $700 bottle of champagne was because of what my “profile” said about me. I would love to see this profile they had on me. I did not appreciate being embarrassed in front of my wife. We spent close to 10K at this place for the 7 days we spent there. We chose to stay at Trump Intl in Chicago because we can afford to do so. I understood before checking in that it would be very expensive. I did not know that a profile would be built about me and I would be judged by the staff according to it. I will never stay at a Trump hotel again. There are too many hotels to chose from to have to deal with this kind of treatment.

Reviewed on 12 Jul 2025

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
per person
20 Sept - 26 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,037 reviews)
My favorite hotel in Chicago! Always a fabulous time and the staff are delightful!

Reviewed on 11 Jul 2025

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

Top hotels in Westchester

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £129 per night from 5 Aug to 6 Aug
£129
5 Aug - 6 Aug
includes taxes & fees
7.8/10 Good! (8,930 reviews)
"Good location.good staff."

Reviewed on 9 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is £197 per night from 10 Aug to 11 Aug
£197
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,009 reviews)
"We had a wonderful stay at the Intercontinental Magnificent Mile over the July 4th weekend! We enjoyed all 3 restaurants/bars- especially Casa Chi! The staff were all excellent. The spot is super convenient/walkable to everywhere you would want to go in downtown Chicago, a block from the riverwalk ..."

Reviewed on 9 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 10 Aug to 11 Aug
£132
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,430 reviews)
"I always prefer staying in Hilton!"

Reviewed on 12 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,982 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

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

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
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Westchester

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Westchester

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.

* 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.