Westchester Holidays from £869

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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 £1,157, price is now £869 per person
£869
per person
28 Aug - 1 Sept
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
I feel very glad my husband and I chose Felix Hotel for our stay in Chicago during early June. The location was great for our purposes, there were plenty of food options near by and the complementary fruit and coffee/tea in the morning was very helpful to get our day started. We felt specially welcomed by Crystal at the front desk. Her friendly personality will be forever remembered as one of the highlights of a wonderful trip.

Reviewed on 18 Jun 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
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 24 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

Great Wolf Lodge Illinois

3 out of 5
Price was £2,341, price is now £1,694 per person
£1,694
per person
1 Aug - 8 Aug
found 24 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

Kinzie Hotel

Kinzie Hotel

4 out of 5
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

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,701, price is now £1,287 per person
£1,287
per person
9 Sept - 14 Sept
found 21 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

Congress Plaza Hotel

3.5 out of 5
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

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £143 per night from 1 Jul to 2 Jul
£143
1 Jul - 2 Jul
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

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £137 per night from 28 Jun to 29 Jun
£137
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,671 reviews)
"Great staff and amenities"

Reviewed on 19 Jun 2026

Hyatt Regency O'Hare Chicago
See all 5,113 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

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£81
per adult
88% of travellers recommend
Chicago C3® by CityPASS®
See all activities in Westchester

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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.