Search Cheap Flights to
Westchester

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Westchester Flights as Low as $43

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Wed, Mar 12 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$43 Roundtrip, found 3 days ago
$43
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Wed, Mar 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Mar 12, priced at $43 found 3 days ago
Frontier Airlines
Tue, Mar 25 - Tue, Apr 1
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$48 Roundtrip, found 6 days ago
$48
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Mar 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, Apr 1, priced at $48 found 6 days ago
Frontier Airlines
Wed, Mar 26 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 2 days ago
$48
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $48 found 2 days ago
Spirit Airlines
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$48 Roundtrip, found 2 days ago
$48
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $48 found 2 days ago
Frontier Airlines
Wed, Mar 5 - Wed, Mar 12
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$54 Roundtrip, found 2 days ago
$54
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 12, priced at $54 found 2 days ago
Spirit Airlines
Wed, Mar 19 - Wed, Mar 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$55 Roundtrip, found 16 hours ago
$55
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Mar 19 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Mar 19, priced at $55 found 16 hours ago
Spirit Airlines
Tue, Mar 25 - Tue, Apr 1
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$57 Roundtrip, found 6 days ago
$57
Roundtrip
found 6 days ago
Select Spirit Airlines flight, departing Tue, Mar 25 from George Bush Intercontinental to O'Hare Intl., returning Tue, Apr 1, priced at $57 found 6 days ago
Frontier Airlines
Wed, Mar 26 - Mon, Apr 7
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 2 days ago
$58
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 26 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Apr 7, priced at $58 found 2 days ago
Spirit Airlines
Tue, Apr 1 - Wed, Apr 2
MSY
Louis Armstrong New Orleans Intl.
ORD
O'Hare Intl.
$78 Roundtrip, found 2 days ago
$78
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Tue, Apr 1 from Louis Armstrong New Orleans Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $78 found 2 days ago
Delta
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 2 days ago
$134
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $134 found 2 days ago
Frontier Airlines
Thu, Apr 10 - Tue, Apr 15
MSY
Louis Armstrong New Orleans Intl.
MDW
Midway Intl.
$135 Roundtrip, found 14 hours ago
$135
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Thu, Apr 10 from Louis Armstrong New Orleans Intl. to Midway Intl., returning Tue, Apr 15, priced at $135 found 14 hours ago
United
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$139 Roundtrip, found 2 days ago
$139
Roundtrip
found 2 days ago
Select United flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $139 found 2 days ago
American Airlines
Wed, Apr 2 - Wed, Apr 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$159 Roundtrip, found 2 days ago
$159
Roundtrip
found 2 days ago
Select American Airlines flight, departing Wed, Apr 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Apr 2, priced at $159 found 2 days ago
Frontier Airlines
Fri, Feb 21 - Wed, Feb 26
IAH
George Bush Intercontinental
MDW
Midway Intl.
$180 Roundtrip, found 1 day ago
$180
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Feb 21 from George Bush Intercontinental to Midway Intl., returning Wed, Feb 26, priced at $180 found 1 day ago
JetBlue Airways
Sat, Mar 8 - Tue, Mar 11
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$309 Roundtrip, found 3 days ago
$309
Roundtrip
found 3 days ago
Select JetBlue Airways flight, departing Sat, Mar 8 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Mar 11, priced at $309 found 3 days ago
Delta
Fri, Jun 13 - Tue, Jun 17
CMH
John Glenn Columbus Intl.
MDW
Midway Intl.
$317 Roundtrip, found 2 days ago
$317
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Jun 13 from John Glenn Columbus Intl. to Midway Intl., returning Tue, Jun 17, priced at $317 found 2 days ago

Cheap Flights to Westchester

Fall in love at first flight with your vacation to Westchester by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Westchester on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Westchester, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Westchester

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Westchester with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Westchester?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Westchester are in March, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Westchester?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Westchester.

What airport is best to fly into Westchester?

When you’re planning your trip to Westchester, convenience is the name of the game. Luckily, Westchester Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Westchester must-do list.

How much are flights to Westchester?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Westchester on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $43, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Westchester?

The trick to saving a stack of cash on your flight to Westchester? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $43 right now, why wait?

Westchester Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$42

Last Minute Hotel Deals in Westchester

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
The price is $103 per night from Feb 26 to Feb 27
$103
includes taxes & fees
Feb 26 - Feb 27
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,800 reviews)
"Excellent location, restaurants closed the hotel, accessible bus stations to move around the city and Nice view to Chicago River."

Reviewed on Feb 17, 2025

River Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is $115 per night from Feb 23 to Feb 24
$115
includes taxes & fees
Feb 23 - Feb 24
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
7.8/10 Good! (8,508 reviews)
"The city"

Reviewed on Feb 18, 2025

Congress Plaza Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
The price is $151 per night from Feb 23 to Feb 24
$151
includes taxes & fees
Feb 23 - Feb 24
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
9.6/10 Exceptional! (1,653 reviews)
"The hotel is well-kept and the staff is very friendly and helpful. The amenities are great, the cost is affordable, and the area surrounding the location is really walkable and accessible."

Reviewed on Feb 17, 2025

L7 Chicago by LOTTE
Hilton Chicago
Hilton Chicago
4 out of 5
720 S Michigan Ave, Chicago, IL
The price is $204 per night from Feb 28 to Mar 1
$204
includes taxes & fees
Feb 28 - Mar 1
Stay at this 4-star historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.2/10 Very Good! (1,658 reviews)
"Beautiful hotel in the perfect area"

Reviewed on Feb 18, 2025

Hilton Chicago
Hyatt Regency O'Hare Chicago
Hyatt Regency O'Hare Chicago
4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
The price is $132 per night from Feb 22 to Feb 23
$132
includes taxes & fees
Feb 22 - Feb 23
Book a stay at this eco-certified hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,302 reviews)
"The room was beautiful"

Reviewed on Feb 18, 2025

Hyatt Regency O'Hare Chicago
citizenM Chicago Downtown
citizenM Chicago Downtown
4 out of 5
80 East Wacker Place, Chicago, IL
The price is $117 per night from Feb 23 to Feb 24
$117
includes taxes & fees
Feb 23 - Feb 24
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the breakfast and the ...
9.2/10 Wonderful! (2,681 reviews)
"Thanks for the stay"

Reviewed on Feb 17, 2025

citizenM Chicago Downtown
Hyatt Regency Chicago
Hyatt Regency Chicago
4 out of 5
151 East Wacker Dr, Chicago, IL
The price is $231 per night from Mar 21 to Mar 22
$231
includes taxes & fees
Mar 21 - Mar 22
Book a stay at this eco-certified hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our ...
9.2/10 Wonderful! (3,203 reviews)
"Amazing stay"

Reviewed on Feb 17, 2025

Hyatt Regency Chicago
Hotel Riu Plaza Chicago
Hotel Riu Plaza Chicago
4 out of 5
150 East Ontario Street, Chicago, IL
The price is $132 per night from Feb 24 to Feb 25
$132
includes taxes & fees
Feb 24 - Feb 25
Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Millennium Park are located nearby.
9.2/10 Wonderful! (1,472 reviews)
"First class service"

Reviewed on Feb 18, 2025

Hotel Riu Plaza Chicago
See all 4,713 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.