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Westchester

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Westchester Flights as Low as $113

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

JetBlue Airways
Thu, Sep 4 - Thu, Sep 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$113 Roundtrip, found 1 hour ago
$113
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Sep 4 from Logan Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $113 found 1 hour ago
American Airlines
Thu, Sep 4 - Thu, Sep 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 1 hour ago
$119
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Thu, Sep 4 from Logan Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $119 found 1 hour ago
Frontier Airlines
Thu, Aug 21 - Thu, Aug 28
RDU
Raleigh - Durham Intl.
ORD
O'Hare Intl.
$121 Roundtrip, found 1 day ago
$121
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Aug 21 from Raleigh - Durham Intl. to O'Hare Intl., returning Thu, Aug 28, priced at $121 found 1 day ago
JetBlue Airways
Thu, Sep 4 - Thu, Sep 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$123 Roundtrip, found 1 hour ago
$123
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Sep 4 from Logan Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $123 found 1 hour ago
JetBlue Airways
Wed, Sep 3 - Mon, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$129 Roundtrip, just found
$129
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Sep 3 from Logan Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $129 just found
United
Wed, Sep 3 - Mon, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$129 Roundtrip, just found
$129
Roundtrip
just found
Select United flight, departing Wed, Sep 3 from Logan Intl. to O'Hare Intl., returning Mon, Sep 8, priced at $129 just found
Delta
Sat, Aug 30 - Sun, Aug 31
BOS
Logan Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 4 days ago
$138
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 30 from Logan Intl. to O'Hare Intl., returning Sun, Aug 31, priced at $138 found 4 days ago
Spirit Airlines
Sat, Aug 16 - Tue, Aug 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$141 Roundtrip, found 5 days ago
$141
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, Aug 16 from Los Angeles Intl. to O'Hare Intl., returning Tue, Aug 19, priced at $141 found 5 days ago
Bargain Flight
Thu, Sep 4 - Thu, Sep 4
MEM
Memphis Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 6 hours ago
$153
Roundtrip
found 6 hours ago
Select Bargain Flight flight, departing Thu, Sep 4 from Memphis Intl. to O'Hare Intl., returning Thu, Sep 4, priced at $153 found 6 hours ago
Delta
Sat, Sep 6 - Sat, Sep 6
RDU
Raleigh - Durham Intl.
MDW
Midway Intl.
$194 Roundtrip, found 2 days ago
$194
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Sep 6 from Raleigh - Durham Intl. to Midway Intl., returning Sat, Sep 6, priced at $194 found 2 days ago
Delta
Tue, Oct 14 - Tue, Oct 21
MEM
Memphis Intl.
MDW
Midway Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 14 from Memphis Intl. to Midway Intl., returning Tue, Oct 21, priced at $197 found 3 days ago
Delta
Sat, Oct 25 - Sat, Oct 25
LAX
Los Angeles Intl.
MDW
Midway Intl.
$211 Roundtrip, found 11 hours ago
$211
Roundtrip
found 11 hours ago
Select Delta flight, departing Sat, Oct 25 from Los Angeles Intl. to Midway Intl., returning Sat, Oct 25, priced at $211 found 11 hours ago
Alaska Airlines
Sat, Nov 15 - Wed, Nov 19
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 4 hours ago
$216
Roundtrip
found 4 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 4 hours ago
Sun Country Airlines
Fri, Sep 26 - Mon, Sep 29
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$277 Roundtrip, found 3 days ago
$277
Roundtrip
found 3 days 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 3 days ago
Delta
Wed, Aug 20 - Tue, Aug 26
BOS
Logan Intl.
MDW
Midway Intl.
$279 Roundtrip, found 2 days ago
$279
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Aug 20 from Logan Intl. to Midway Intl., returning Tue, Aug 26, priced at $279 found 2 days ago
Hawaiian Airlines
Mon, Nov 17 - Sat, Nov 22
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$348 Roundtrip, found 1 day ago
$348
Roundtrip
found 1 day ago
Select Hawaiian Airlines flight, departing Mon, Nov 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Nov 22, priced at $348 found 1 day 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 September, 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 15 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 $113, 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 $113 right now, why wait?

Westchester Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$113

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! (8,939 reviews)
Historic Charmer
"GORGEOUS view of downtown and Lake Michigan! Light filled room. Comfortable bed. Bathtub to welcome zen. Restful sleep nightly to embrace the day ahead. All staff were welcoming and helpful. Gym more than sufficient for maintaining my fitness goals while traveling. I appreciate renovated spaces that ..."

Reviewed on Jul 22, 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! (2,091 reviews)
"The location and staff were excellent. The conditions of the rooms were below expectation considering the price and the brand. There were visible signs of wear and tear in the units. Our first room was musty and smelled like it had been smoked in. The corners of the bench at the foot of the bed was ..."

Reviewed on Jul 22, 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! (2,528 reviews)
"Convenient to the public transportation and nearby shopping. On-site restaurant was a good breakfast option for us before heading out for the day."

Reviewed on Jul 24, 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! (1,307 reviews)
"Great location"

Reviewed on Jul 23, 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! (4,526 reviews)
"Excellent all around"

Reviewed on Jul 23, 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! (3,438 reviews)
Fantastic find in Chicago
"What a great hotel -selected from many close to my conference at the Hyatt. It was also walking distance (1.2 miles) from Union Station (Amtrak). Hotel check-in and check-out is seamless -all done at central kiosk. Hotel staff ever-present to assist. Rooms are exceptionally clean and comfortable. ..."

Reviewed on Jul 24, 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
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
7.8/10 Good! (2,096 reviews)
"Perfect location just the interior is way too dark …. It’s not a night club !"

Reviewed on Jul 22, 2025

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Freehand Chicago
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.