Westchester Holidays from AU$636

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Your Westchester Holiday

Book a tailored Westchester holiday package that includes everything you need and nothing you don't. Good for nightlife, bars and pubs and cafes, consider staying in the neighbourhood of Wicker Park. Any trip to Westchester needs a well-planned itinerary. Fill yours with leading attractions like Brookfield Zoo, Oakbrook Centre Mall and Ernest Hemingway Museum and House. Your dream Westchester holiday is only clicks away. Browse hotels, flights and more on Expedia for an adventure that's tailored to suit your travel style.

The Latest Westchester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Lombard Oak Brook

Embassy Suites by Hilton Chicago Lombard Oak Brook

3.5 out of 5
Price was AU$737, price is now AU$636 per person
AU$636
per person
5 Aug - 8 Aug
found 1 day ago
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
8.2/10 Very good! (1,662 reviews)
Everything was wonderful

Reviewed on 2 July 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was AU$1,882, price is now AU$1,508 per person
AU$1,508
per person
5 Aug - 8 Aug
found 1 day ago
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
We had a great stay at Level. I think it’s a really good option for a longer trip, especially if you want more of an apartment-style setup and a convenient location. The staff was amazing from start to finish and truly made the stay stand out. Everyone was kind, helpful, and welcoming, and the service alone would make me come back. The location is also very convenient and worked well for getting around Chicago, especially if you don’t mind doing a bit of walking. For our family, I think it felt a little more geared toward professionals or longer stays than a traditional family hotel, but overall we had a very positive experience. If you’re staying in Chicago for more than a couple of nights and want something comfortable and convenient, I would definitely recommend it.

Reviewed on 2 July 2026

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was AU$1,201, price is now AU$974 per person
AU$974
per person
5 Aug - 8 Aug
found 1 day ago
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
8.4/10 Very good! (2,332 reviews)
I have severe mobility issues, but was taken by wheelchair directly from United gate to Hilton reception desk. Restaurants were close to reception and elevators, so accessible with stroller.

Reviewed on 2 July 2026

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Price was AU$835, price is now AU$695 per person
AU$695
per person
5 Aug - 8 Aug
found 1 day ago
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
8.8/10 Excellent! (1,649 reviews)
Thanks

Reviewed on 2 July 2026

Saratoga Motel By Capital O Near Midway Airport Chicago IL

Saratoga Motel By Capital O Near Midway Airport Chicago IL

2.5 out of 5
Ashburn
Price was AU$763, price is now AU$652 per person
AU$652
per person
5 Aug - 8 Aug
found 1 day ago
Return direct flight included
Las Vegas (LAS) to Chicago (ORD)
6/10 (66 reviews)
Rooms need more attention to details with cleaning bed sheets needs to be new stayings on bed.Sheets and towels

Reviewed on 25 June 2026

Westchester Holiday

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
Rosemont Theatre, Brookfield Zoo and Parkway Bank Park Entertainment District

Our pick of the best Westchester Hotel Deals

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 AU$209 per night from 6 July to 7 July
AU$209
6 July - 7 July
includes taxes & fees
8/10 Very good! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on 2 July 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$311 per night from 5 July to 6 July
AU$311
5 July - 6 July
includes taxes & fees
9.2/10 Wonderful! (1,834 reviews)
"We enjoyed a mini vacation to our favorite hotel in Chicago. This is our fourth time staying with the Omni and they never disappoint. Easy walk to the Red Line to head to a Cubs game. Steps away from shopping, bars, and restaurants. Thanks for another amazing stay."

Reviewed on 2 July 2026

Omni Chicago Hotel
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 AU$342 per night from 5 July to 6 July
AU$342
5 July - 6 July
includes taxes & fees
9/10 Wonderful! (4,481 reviews)
"My refrigerator didn't work at all I reported it to the front desk no one came and fix it I wasted two expensive dinners I had purchased"

Reviewed on 2 July 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,952 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
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All Inclusive Holidays
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beach holidays
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What to do in Westchester

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Westchester

Frequently asked questions

How much does a Westchester holiday package cost?
You'll find cheap prices from AU$636 on Expedia for your Westchester getaway. However, factors like the season, choice of hotel and length of stay will influence how much your holiday to Westchester costs.
What are the cheapest months to go to Westchester?
If you're hoping to score a cheap Westchester holiday package, consider planning a trip in November, December and January. You'll usually find lower prices on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Westchester?
The ideal duration for your Westchester holiday depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to tick off all the main sights and explore some hidden spots along the way.
How to find the best Westchester package deals?
Bagging a cheap Westchester package deal is a cinch with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and browse what's available. You can personalise your search by "Popular locations," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to view the most economical Westchester package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Westchester holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll typically snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Westchester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Westchester?
Land incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for a spur-of-the-moment Westchester escape.
How to plan a trip to Westchester?

  1. Pick the perfect time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Westchester.
  2. Set your budget: Factor in expenses like flights, transportation and food when calculating how much to put aside for your trip to Westchester. Then, select a property that works with your budget, whether that's a wallet-friendly stay or a high-end retreat.
  3. Decide how long to go away for: Now that you're more familiar with Westchester, you can work out the right length of your break. Put together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your accommodation and airfare: After you've nailed down your trip dates and duration, book the ideal Westchester holiday package for you.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.