Westchester Holidays

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    Save up to €900 when you book a flight and hotel together*

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Top hotels in Westchester

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 €179 per night from 26 Jul to 27 Jul
€179
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very good! (1,691 reviews)
"Location Location Location !! Friendly welcoming staff Nice upkeep of legendary Chicago hotel. Rooms decent side. Excellent water pressure in shower. Only suggestion would be to replace dated carpet in hotel room with laminate flooring. The carpet is tired looking"

Reviewed on 5 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 €126 per night from 7 Jul to 8 Jul
€126
7 Jul - 8 Jul
includes taxes & fees
8/10 Very good! (10,171 reviews)
"First, the parking is not accessible through the building. It was raining when we arrived. The parking is a regular open lot that is $62 and nothing special. You cannot enter the building from the parking lot. We had to walk over a block in the rain carrying all our luggage. Next, when we stepped ..."

Reviewed on 5 Jul 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 €181 per night from 8 Jul to 9 Jul
€181
8 Jul - 9 Jul
includes taxes & fees
9.2/10 Wonderful! (1,853 reviews)
"Clean room, pullout couch was ready and good quality. Restaurant / bar proved to be really good and convenient. Staff there were very friendly. Location is excellent. Needing 2 elevators to reach your room is inconvenient, but this seems to be the standard in the area."

Reviewed on 5 Jul 2026

Omni Chicago Hotel
See all 4,882 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.

What to do in Westchester

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€40
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€35
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 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.