Westchester Holidays from £1,073
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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.
Kinzie Hotel
Downtown Chicago
Price was £1,444, price is now £1,073 per person
£1,073
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (2,146 reviews)
I truly enjoy. Can’t wait to check in again and would love to have some type of reward program for a better rate.
Reviewed on 18 Jun 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was £5,754, price is now £3,748 per person
£3,748
per person
1 Aug - 8 Aug
found 22 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
There charges are not clear, unnecessary security deposit, long hold period and I don't even know if they refunded my security deposit as haven't received any bill/receipt post checkout
Reviewed on 18 Jun 2026
Great Wolf Lodge Illinois
Price was £2,341, price is now £1,694 per person
£1,694
per person
1 Aug - 8 Aug
found 22 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
First time staying at a Great Wolf Lodge. Was a wonderful time. Onsite food selection was great and easy to order ahead of time if wanted. Waterpark was as expected. Many other activities available to keep the kids entertained was a nice touch. Arcade is expensive and having to pay to park were my only disappointments. Otherwise highly recommend!
Reviewed on 18 Jun 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was £2,275, price is now £1,651 per person
£1,651
per person
9 Sept - 14 Sept
found 20 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.6/10 Exceptional! (1,888 reviews)
Very clean rooms, helpful staff and great amenities! Close to everything and convenient to shopping and eating
Felt safe and comfortable in the area !
Reviewed on 15 Jun 2026
The Emily Hotel
Downtown Chicago
Price was £1,701, price is now £1,287 per person
£1,287
per person
9 Sept - 14 Sept
found 20 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
We stayed at this hotel for a small wedding venue. I booked the larger room and was glad I did. The hotel was close for walking to restaurants and some bars. The front desk was very friendly and helpful.
Reviewed on 19 Jun 2026
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
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is £123 per night from 29 Jun to 30 Jun
£123
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"The facilities are very old, and there is a musty smell in the room."
Reviewed on 18 Jun 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is £122 per night from 28 Jun to 29 Jun
£122
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,595 reviews)
"seems like we are visiting every other month to meet up with friends. We have already recommended this hotel many times and will definitely be staying again."
Reviewed on 19 Jun 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £117 per night from 28 Jun to 29 Jun
£117
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,670 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."
Reviewed on 17 Jun 2026
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.
What to do in Westchester
Wendella's 90-min Chicago River Architecture Tour
£30
per adult
94% of travellers recommend
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* 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.
