$21 Cheap Flights to Westchester , IL

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How much is the cheapest flight to Westchester?

Prices were available within the past 7 days and start at $21 for one-way flights and $41 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Tue, Aug 27 - Tue, Aug 27
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$43 Roundtrip, found 5 hours ago
$43
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Tue, Aug 27 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Aug 27, priced at $43 found 5 hours ago
Spirit Airlines
Tue, Jun 11 - Wed, Jun 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$51 Roundtrip, just found
$51
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jun 11 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Jun 12, priced at $51 just found
Spirit Airlines
Tue, Jun 4 - Sat, Jun 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$60 Roundtrip, just found
$60
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Jun 4 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Jun 8, priced at $60 just found
Frontier Airlines
Sun, May 26 - Wed, May 29
PHL
Philadelphia Intl.
MDW
Midway Intl.
$62 Roundtrip, just found
$62
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, May 26 from Philadelphia Intl. to Midway Intl., returning Wed, May 29, priced at $62 just found
Frontier Airlines
Sun, May 26 - Wed, May 29
PHL
Philadelphia Intl.
ORD
O'Hare Intl.
$63 Roundtrip, just found
$63
Roundtrip
just found
Select Frontier Airlines flight, departing Sun, May 26 from Philadelphia Intl. to O'Hare Intl., returning Wed, May 29, priced at $63 just found

Find Your Flights to Westchester CHI

Cheap flights to Westchester (CHI)

Get started finding a cheap flight to Westchester on Expedia by either choosing a deal on this page or entering into the search bar your travel dates, origin airport, and whether you want roundtrip or one-way airfare. You can filter for flexibility, number of stops, airline, and departure/arrival times to find the best flight for you.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Westchester.

Roundtrip prices range from $41 - $63, and one-ways to Westchester start as low as $21.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

Airlines that fly to Westchester (CHI)

You have several options for which airline you choose to travel with to Westchester. There are 10 airlines flying into CHI: Frontier Airlines, Spirit Airlines. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check a bag or bring a carry-on, check whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked/carry-on baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programs may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel in one online platform.

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at the optimal times. Airfare to Westchester (CHI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for roundtrips to CHI in August and in August for one-ways.

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24-hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Frequently asked questions

How do I find cheap flights to Westchester that have flexible change policies?
By using our neat “No change fee” filter, that’s how. Just enter your travel dates, click “Search,” then mark the checkbox underneath the “Flexible change policies” subheading (left-hand side of your screen). Expedia makes it a cinch to find flexible, low-cost flights to Westchester.
What is the name of the airport in Westchester?
If you’re heading for Westchester, there are a few options. Midway Intl. Airport (MDW) is the main one, followed by O’Hare Intl. Airport (ORD).
How far is O'Hare Airport from central Westchester?
It’s 14 mi from ORD to downtown Westchester. Make things easy by researching the best way of getting from the terminal to the city center before you land.
How can I book the cheapest flight to Westchester?
To improve your chances of finding the cheapest flight, enter your travel details into the search fields, then filter the results by your preferred airline, departure and arrival times, and number of stops on your route. Also compare the prices of flying into and out of other airports if that’s an option. Timing is key when it comes to clinching a bargain — book domestic flights at least four weeks out and international flights around six months before departure to save an average of 10%. And if you see a good deal, book it before it’s gone! One of the cheapest flights to Westchester currently is $19, departing Charlotte in June. Wherever you’ll be jetting in from, Expedia will get you on your way to Westchester for the cheapest price possible.
Which day of the week is the best day to buy a plane ticket to Westchester?
Based on our research, Sundays are the best day to purchase a plane ticket. Airfares do fluctuate with demand though, so it’s wise to check prices regularly. Want another tip? Begin browsing airfares to Westchester as soon as you’ve chosen your travel dates and be ready to book when you spot a bargain. The optimal booking window is from 21 days to about 45 days out from takeoff, so the earlier you start looking, the better your chances are of scoring a fantastic deal! Savings are subject to change and may vary depending on selections made.
What airport is best to fly into Westchester?
If you’re planning on hopping on a flight to Westchester, you’ll likely touchdown at O’Hare Airport (14 mi from downtown). MDW (13 mi from downtown) is the other main airport here.
Which airlines fly to Westchester?
You can choose from 47 airlines that connect Westchester with 233 airports around the world, including United Airlines. New York is the most popular departure point for United Airlines flights to Westchester. American Airlines also operates regular services to this destination.
How many nonstop flights are there to Westchester?
Flying to a new place is much more straightforward when there aren’t any lengthy stopovers. If you’re heading to Westchester, the great news is that there are 7,977 direct flights operating every week.
Where are the most popular flights to Westchester departing from?
A large number of flights to Westchester set off from New York, Dallas and Phoenix airports.
Do you have any tips for my flight to Westchester?

  • Get your trip off to a promising start by being prepared. Pack your passport or ID, travel documents and medications first. Next, think about downloading your favorite series on your tablet for a binge session sans guilt. Or, throw in that juicy bestseller you’ve been itching to read. Lastly, a few healthy snacks and a blow-up neck pillow will go a long way to making the trip as comfy as possible.
  • There’s a list of items you should not pack in your carry-on too. Flammables, sharps and explosives are strictly prohibited in the cabin — they often include box cutters, razor blades, flares and aerosol cans. Some sporting equipment, such as baseball bats and martial arts weapons like nunchucks, also generally can’t go in your hand luggage. Visit your airline’s website for details about what you can and can’t take on board.

What to wear on a flight:

  • The aisles of an aircraft aren’t suitable for a fashion show. Layer up with comfortable clothing and bring a pullover as it can get cool in the cabin during long-haul flights. Enclosed, flat shoes are the best type of footwear for longer journeys.
  • The condition known as deep vein thrombosis (DVT) is a risk on long-haul flights. It’s the result of blood clotting due to inactivity and poor circulation. Walking up and down the aisle and doing leg and foot exercises while seated can help prevent this developing. Wearing compression socks or tights can also help to lessen your risk.

How can I get a cheap last-minute flight to Westchester?
The key to booking a cheap last-minute flight to Westchester is to stay flexible. You can land an unbeatable deal if you’re not tied to specific airlines, travel dates and flight times. Also compare the prices of flying out of and into alternative airports if that’s an option.
Where can I learn more about changing or canceling my flight to Westchester?
Most flights are free to cancel within 24 hours of making the reservation. However, some flights are non-refundable, and you may receive a flight credit from the airline to use for a future booking. For more information, please visit our Customer Service Portal.
Flights to Westchester information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
$40

Trending flights to Westchester

Prices were available within the past 7 days and start at $21 for one-way flights and $41 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Spirit Airlines
Tue, May 28 - Wed, May 29
LGA
LaGuardia
ORD
O'Hare Intl.
$41 Roundtrip, just found
$41
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, May 28 from LaGuardia to O'Hare Intl., returning Wed, May 29, priced at $41 just found
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