Cheap Flights to Westchester from $21

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How Much Does it Cost To Fly To Westchester?

The cheapest prices found with in the last 7 days for return flights were $41 and $21 for one-way flights to Westchester for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
CMHChicagoMay 22 to May 26$124
CMHChicagoMay 14 to June 1$136
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
CMHChicagoApril 27 to May 18$304
CMHChicagoApril 28 to May 15$351
*Prices include taxes and fees

Westchester ORD Flight Information

Traveling to
Westchester ORD
Lowest Price
$41
Number of Airlines Serving
16
Airlines Serving
Spirit Airlines, United, American Airlines
Number of Daily Flights
43
Airlines with Direct Flights
American Airlines, Qatar Airways, JAL, Aer Lingus, Emirates, Air New Zealand, United Airlines, Alaska Airlines, Cathay Pacific, Turkish Airlines, SAS, Royal Jordanian, Iberia, ANA, Lufthansa, British Airways

Find The Perfect Hotel For After Your Flight

Amazing Westchester Accommodation Deals

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

3 out of 5
2222 Enterprise Drive, Westchester, IL
The price is $93 per night from May 23 to May 24
$93
per night
May 23 - May 24
Stay at this business-friendly hotel in Westchester. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (999 reviews)
"Great staff"

Reviewed on Apr 21, 2024

Four Points by Sheraton Chicago Westchester/Oak Brook
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.

Luxury Hotels in Westchester

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

3 out of 5
2222 Enterprise Drive, Westchester, IL
The price is $93 per night from May 23 to May 24
$93
per night
May 23 - May 24
Stay at this business-friendly hotel in Westchester. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (999 reviews)
"Great staff"

Reviewed on Apr 21, 2024

Four Points by Sheraton Chicago Westchester/Oak Brook
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.

Family Friendly Hotels in Westchester

Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

3 out of 5
2222 Enterprise Drive, Westchester, IL
The price is $93 per night from May 23 to May 24
$93
per night
May 23 - May 24
Stay at this business-friendly hotel in Westchester. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (999 reviews)
"Great staff"

Reviewed on Apr 21, 2024

Four Points by Sheraton Chicago Westchester/Oak Brook
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.

Best Westchester Flight and Hotel Packages

Westchester flight + hotel packages - economy flights

Prices and availability subject to change. Additional terms may apply.
Fairmont Chicago at Millennium Park Gold Experience
21c Museum Hotel Chicago
The Glen Club
Don't see what you're looking for?
See all available trips from CMH-All Airports to Westchester
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Westchester flight + hotel packages - premium economy flights

Prices and availability subject to change. Additional terms may apply.
JW Marriott Chicago
Hyatt Place Chicago/Downtown - The Loop
Congress Plaza Hotel
Don't see what you're looking for?
See all available trips from CMH-All Airports to Westchester
View all trips

Need a Car For After Your Flight?

Frequently asked questions

Which airlines fly to Westchester?
Getting ready to explore the world? Hoping to begin in Westchester? Just a few of the 20 air carriers that fly here include:

  • United Airlines
  • American Airlines
  • Southwest Airlines

What airport is best to fly into Westchester?
Before you book your flight to Westchester, think about where you’ll stay. This might help you choose which airport would be best for you to touch down at. O’Hare Intl. Airport (ORD) is 9 mi from the center of the city, while Midway Intl. Airport (MDW) is 9 mi from all the action downtown.
Where to stay in Westchester
Life is one incredible journey, so why not get out there and experience it in Westchester? You can begin by selecting from the 296 sensational properties available through Travelocity.Treat yourself to a little extravagance at the Le Méridien Chicago - Oakbrook Center or the Hyatt Lodge. After all, it’s not every day you take a vacation! If you’re the type of wanderer who prefers to spend all their time out exploring, a swanky suite may not be your style. Some fantastic budget options are the Rodeway Inn Lyons - La Grange and the FairBridge Inn Express Melrose Park.
Places to visit in Westchester
If you feel like a sightseeing adventure, you’re in for a treat at Brookfield Zoo. This notable attraction is well worth visiting.Oakbrook Center Mall is wonderful retail destination, with an impressive range of stores and eateries. Want some more ideas? Sharpen your swing and maybe knock a few strokes off your scorecard at Oak Brook Golf Course. But that’s not all there is. Anyone who enjoys nature will enjoy wandering around the unspoiled York Woods County Forest Preserve.
How to get through airport security fast when traveling to Westchester
If you like the thought of spending more time at the airport bars and restaurants and less time wading through security on your way to Westchester, just follow these useful tips:

  • Ensure your boarding pass and travel ID are not difficult to reach. You will be instructed to show them straightaway.
  • It’s important to know that belts with metal buckles can set off the body scanner’s alarms. If you have one on, you may be told to place it in a tray before continuing.
  • Laptops, tablets and other electronic devices must be placed in separate trays to be X-rayed.
  • Flying with a favorite cologne? As long as it contains no more than 3.4 ounces (100 milliliters) and it’s stored in a clear resealable plastic bag, you can keep it with you in your carry-on luggage.
  • Airport security staff will likely tell you to take off your shoes for the body scanner. Wear a pair that you can take off easily. There’s nothing worse than having to do up your laces over and over again.
  • Stash any multi-tools or other sharp items inside your checked luggage. Airport security won’t allow such things in carry-on baggage.

How to find cheap flights

What is the best day to buy a plane ticket?

Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you’re looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you’re browsing flight deals.

 

What are the cheapest days to fly?

Frequent travellers may already know this, earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.

 

How far in advance can you book a flight?

Here’s the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.

*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Plane Tickets To Westchester

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Westchester. Browse through our inventory to explore a wide range of cheap flights to Westchester to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Westchester as you anxiously await to exit the plane and explore what Westchester has to offer. Considering all the amazing local food and culture in Westchester, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Westchester to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Westchester without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Westchester with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Westchester today!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.