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Westchester

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Westchester Flights as Low as $83

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

Frontier Airlines
Tue, Oct 6 - Wed, Oct 21
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 1 day ago
$83
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Oct 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, Oct 21, priced at $83 found 1 day ago
Frontier Airlines
Mon, Nov 16 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$84 Roundtrip, found 1 day ago
$84
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Nov 19, priced at $84 found 1 day ago
Frontier Airlines
Wed, Oct 21 - Thu, Oct 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$96 Roundtrip, found 1 day ago
$96
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Thu, Oct 29, priced at $96 found 1 day ago
Frontier Airlines
Mon, Nov 23 - Thu, Dec 3
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Mon, Nov 23 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Dec 3, priced at $100 found 1 day ago
Frontier Airlines
Tue, Nov 17 - Thu, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$104 Roundtrip, found 1 day ago
$104
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Nov 17 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Nov 19, priced at $104 found 1 day ago
Bargain Flight
Sat, Oct 3 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$176 Roundtrip, found 1 day ago
$176
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Oct 3 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Oct 5, priced at $176 found 1 day ago
Bargain Flight
Mon, Nov 16 - Wed, Nov 18
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$185 Roundtrip, found 5 hours ago
$185
Roundtrip
found 5 hours ago
Select Bargain Flight flight, departing Mon, Nov 16 from Ronald Reagan Washington National to O'Hare Intl., returning Wed, Nov 18, priced at $185 found 5 hours ago
American Airlines
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $197 found 1 day ago
Delta
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $197 found 1 day ago
Southwest Airlines
Wed, Dec 2 - Tue, Dec 15
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$197 Roundtrip, found 5 hours ago
$197
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 15, priced at $197 found 5 hours ago
United
Wed, Oct 14 - Sat, Oct 17
IAD
Washington Dulles Intl.
ORD
O'Hare Intl.
$212 Roundtrip, found 20 hours ago
$212
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Oct 14 from Washington Dulles Intl. to O'Hare Intl., returning Sat, Oct 17, priced at $212 found 20 hours ago
Delta
Wed, Oct 28 - Sat, Oct 31
IAD
Washington Dulles Intl.
MDW
Midway Intl.
$232 Roundtrip, found 1 day ago
$232
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Oct 28 from Washington Dulles Intl. to Midway Intl., returning Sat, Oct 31, priced at $232 found 1 day ago
Southwest Airlines
Fri, Nov 27 - Tue, Dec 1
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Nov 27 from Ronald Reagan Washington National to Midway Intl., returning Tue, Dec 1, priced at $255 found 1 day ago
Frontier Airlines
Wed, Oct 28 - Sat, Oct 31
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$256 Roundtrip, found 2 days ago
$256
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Oct 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Sat, Oct 31, priced at $256 found 2 days ago
JetBlue Airways
Wed, Dec 2 - Tue, Dec 8
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$319 Roundtrip, found 1 day ago
$319
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, Dec 2 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 8, priced at $319 found 1 day ago
KEY LIME AIR DBA DENVER AIR CONNECTION
Mon, Sep 21 - Sat, Sep 26
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$507 Roundtrip, found 7 hours ago
$507
Roundtrip
found 7 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Mon, Sep 21 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Sep 26, priced at $507 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 October, 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 14 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 $83, 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 $83 right now, why wait?

Westchester Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$82

Last Minute Hotel Deals in Westchester

River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,459 reviews)
"Location was perfect. Staff were nice."

Reviewed on Sep 16, 2026

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River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
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The Chicago Hotel Collection Ambassador Gold Coast
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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,257 reviews)
"The Congress Plaza Hotel is old, but affordable. If you're not after a high level of comfort and just need a clean and conveniently located place to sleep that is probably more affordable than anywhere else in downtown Chicago, then this hotel should do nicely for you."

Reviewed on Sep 16, 2026

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Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,208 reviews)
"From the very start at check in Stephen was so kind and helpful. Throughout my stay the staff was very friendly. The restaurant was excellent & I was grateful to have a chance to take a swim!"

Reviewed on Sep 15, 2026

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Hilton Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (2,175 reviews)
"The rooms were clean a bit dated but comfortable for my family. Leo (valet) was absolutely the best help while traveling with a toddler. Sadly, we experienced cold water but overall pleasant hotel with great view."

Reviewed on Sep 16, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hampton Inn Chicago Downtown/Magnificent Mile

Hampton Inn Chicago Downtown/Magnificent Mile

2.5 out of 5
160 E Huron Street Chicago IL
Book a stay at this family-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and valet parking (surcharge). Our guests praise the breakfast and the ...
8/10 Very Good! (1,613 reviews)
"Do not stay here. Terrible staff. Long lines. No response from management. Very disappointing."

Reviewed on Sep 15, 2026

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Hampton Inn Chicago Downtown/Magnificent Mile
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (2,681 reviews)
"The location and room itself worked well for us after a wedding on the Southside and using a Spot Hero parking place. The breakfast was very good, made fresh with good options but the tables needed to be bused and wiped down. The lobby needed tending to as well"

Reviewed on Sep 15, 2026

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Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
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Hyatt Regency Chicago
See all 5,020 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.