Westchester Holidays from £720

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £944, price is now £720 per person
£720
per person
14 Jan - 21 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,099, price is now £793 per person
£793
per person
14 Jan - 21 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,318, price is now £977 per person
£977
per person
21 Jan - 26 Jan
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,726, price is now £1,315 per person
£1,315
per person
26 Dec - 31 Dec
found 18 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Limpieza ,atención,todo 100 ,muy complacida y feliz con mi estancia

Reviewed on 3 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,477, price is now £1,127 per person
£1,127
per person
5 Jan - 12 Jan
found 11 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

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 £103 per night from 10 Nov to 11 Nov
£103
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,094 reviews)
"This was an older hotel but very well maintained. I stayed here with my two daughters (19 & 13) and it was spacious enough for us three. We were able to see the fireworks at the pier from our room."

Reviewed on 3 Nov 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £103 per night from 9 Nov to 10 Nov
£103
9 Nov - 10 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £106 per night from 23 Nov to 24 Nov
£106
23 Nov - 24 Nov
includes taxes & fees
River Hotel
See all 5,158 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

What to do in Westchester

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.