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Westchester

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Westchester Flights as Low as $72

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

Spirit Airlines
Sat, Aug 23 - Wed, Aug 27
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 17 hours ago
$72
Roundtrip
found 17 hours ago
Select Spirit Airlines flight, departing Sat, Aug 23 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 27, priced at $72 found 17 hours ago
Frontier Airlines
Tue, Aug 5 - Wed, Aug 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$75 Roundtrip, found 8 hours ago
$75
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Aug 6, priced at $75 found 8 hours ago
Frontier Airlines
Sat, Aug 30 - Wed, Sep 3
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$105 Roundtrip, found 1 day ago
$105
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Sep 3, priced at $105 found 1 day ago
Frontier Airlines
Tue, Aug 5 - Tue, Aug 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$110 Roundtrip, found 10 hours ago
$110
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Aug 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, Aug 12, priced at $110 found 10 hours ago
Spirit Airlines
Sat, Dec 6 - Mon, Dec 8
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$120 Roundtrip, found 16 hours ago
$120
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Sat, Dec 6 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Dec 8, priced at $120 found 16 hours ago
Spirit Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$130 Roundtrip, just found
$130
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $130 just found
Delta
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 11 hours ago
$132
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 11 hours ago
United
Sat, Sep 6 - Sat, Sep 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 11 hours ago
$132
Roundtrip
found 11 hours ago
Select United flight, departing Sat, Sep 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 6, priced at $132 found 11 hours ago
American Airlines
Sat, Aug 30 - Sat, Aug 30
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 20 hours ago
$132
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Sat, Aug 30 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $132 found 20 hours ago
Contour Airlines
Mon, Aug 25 - Thu, Aug 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$189 Roundtrip, found 1 day ago
$189
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Mon, Aug 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $189 found 1 day ago
Delta
Sat, Sep 6 - Sat, Sep 6
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 20 hours ago
$191
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to O'Hare Intl., returning Sat, Sep 6, priced at $191 found 20 hours ago
Delta
Sat, Sep 6 - Tue, Sep 9
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 20 hours ago
$197
Roundtrip
found 20 hours ago
Select Delta flight, departing Sat, Sep 6 from Love Field to Midway Intl., returning Tue, Sep 9, priced at $197 found 20 hours ago
Delta
Sat, Oct 25 - Sat, Oct 25
LAX
Los Angeles Intl.
MDW
Midway Intl.
$211 Roundtrip, just found
$211
Roundtrip
just found
Select Delta flight, departing Sat, Oct 25 from Los Angeles Intl. to Midway Intl., returning Sat, Oct 25, priced at $211 just found
Alaska Airlines
Sat, Nov 15 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 11 hours ago
$216
Roundtrip
found 11 hours ago
Select Alaska Airlines flight, departing Sat, Nov 15 from Los Angeles Intl. to O'Hare Intl., returning Wed, Nov 19, priced at $216 found 11 hours ago
JetBlue Airways
Wed, Oct 15 - Wed, Oct 22
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$272 Roundtrip, found 20 hours ago
$272
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Wed, Oct 15 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 22, priced at $272 found 20 hours ago
Sun Country Airlines
Fri, Sep 26 - Mon, Sep 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 7 hours ago
$277
Roundtrip
found 7 hours ago
Select Sun Country Airlines flight, departing Fri, Sep 26 from Los Angeles Intl. to O'Hare Intl., returning Mon, Sep 29, priced at $277 found 7 hours 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 August, 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 $72, 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 $72 right now, why wait?

Westchester Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$72

Last Minute Hotel Deals in Westchester

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
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! (8,887 reviews)
"I liked that they provided a shower cap. I would prefer if there was a microwave in the room. Overall, it was a great stay."

Reviewed on Jul 19, 2025

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Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (2,070 reviews)
"Great location!"

Reviewed on Jul 19, 2025

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InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
8.8/10 Excellent! (2,510 reviews)
"Safe area and very walkable"

Reviewed on Jul 22, 2025

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Hilton Chicago/Magnificent Mile Suites
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Stay at this 3.5-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
8.8/10 Excellent! (1,293 reviews)
"It was nicely located near the event we were there to visit. It was near Greektown and it gave us good options to walk or uber easily."

Reviewed on Jul 20, 2025

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Crowne Plaza Chicago West Loop by IHG
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
8.4/10 Very Good! (4,498 reviews)
"Good central hotel. Not the"

Reviewed on Jul 20, 2025

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Embassy Suites by Hilton Chicago Downtown River North
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
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! (3,418 reviews)
"Really enjoyed the 4th floor “living room” area and the outdoor patio"

Reviewed on Jul 21, 2025

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citizenM Chicago Downtown
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
8.2/10 Very Good! (3,511 reviews)
"good"

Reviewed on Jul 22, 2025

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The Whitehall Hotel, BW Premier Collection
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8/10 Very Good! (1,907 reviews)
Hotel Felix - July 2025
"Hotel and staff were very nice. Breakfast consists of coffee, tea and fruit. Pastries can be purchased. The room was nice, not what I would consider a 4 star (i.e., not comparable to the nearby Hyatt). Charge of $5 per piece to store luggage."

Reviewed on Jul 21, 2025

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Hotel Felix River North/Magnificent Mile
See all 5,084 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.