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Westchester

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Westchester Flights as Low as $77

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

Delta
Tue, Jul 8 - Tue, Jul 15
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$77 Roundtrip, found 6 days ago
$77
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jul 8 from Minneapolis - St. Paul Intl. to Midway Intl., returning Tue, Jul 15, priced at $77 found 6 days ago
Spirit Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$90 Roundtrip, found 11 hours ago
$90
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $90 found 11 hours ago
Spirit Airlines
Wed, Jul 16 - Wed, Jul 23
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$102 Roundtrip, found 9 hours ago
$102
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Wed, Jul 16 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 23, priced at $102 found 9 hours ago
Spirit Airlines
Mon, Jul 7 - Wed, Jul 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$110 Roundtrip, found 19 hours ago
$110
Roundtrip
found 19 hours ago
Select Spirit Airlines flight, departing Mon, Jul 7 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jul 9, priced at $110 found 19 hours ago
Spirit Airlines
Wed, Jun 11 - Wed, Jun 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$112 Roundtrip, found 12 hours ago
$112
Roundtrip
found 12 hours ago
Select Spirit Airlines flight, departing Wed, Jun 11 from Los Angeles Intl. to O'Hare Intl., returning Wed, Jun 11, priced at $112 found 12 hours ago
Spirit Airlines
Fri, Jul 25 - Wed, Jul 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$114 Roundtrip, found 3 days ago
$114
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Fri, Jul 25 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 30, priced at $114 found 3 days ago
Sun Country Airlines
Tue, Jul 15 - Wed, Jul 16
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 18 hours ago
$127
Roundtrip
found 18 hours ago
Select Sun Country Airlines flight, departing Tue, Jul 15 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $127 found 18 hours ago
Frontier Airlines
Sat, Sep 20 - Sun, Sep 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$138 Roundtrip, found 4 days ago
$138
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Sep 20 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sun, Sep 21, priced at $138 found 4 days ago
Bargain Flight
Fri, Jun 13 - Fri, Jun 27
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Fri, Jun 13 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Fri, Jun 27, priced at $154 found 1 day ago
American Airlines
Wed, Jul 9 - Wed, Jul 16
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$158 Roundtrip, found 11 hours ago
$158
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jul 16, priced at $158 found 11 hours ago
Frontier Airlines
Tue, Jun 24 - Wed, Jun 25
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$171 Roundtrip, found 1 day ago
$171
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Jun 24 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Jun 25, priced at $171 found 1 day ago
Delta
Sat, Jul 5 - Tue, Jul 15
DAL
Love Field
MDW
Midway Intl.
$197 Roundtrip, found 5 days ago
$197
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Jul 5 from Love Field to Midway Intl., returning Tue, Jul 15, priced at $197 found 5 days ago
Delta
Tue, Jul 1 - Sat, Jul 12
DAL
Love Field
ORD
O'Hare Intl.
$200 Roundtrip, found 16 hours ago
$200
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Jul 1 from Love Field to O'Hare Intl., returning Sat, Jul 12, priced at $200 found 16 hours ago
Contour Airlines
Wed, Jul 23 - Mon, Jul 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Wed, Jul 23 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Mon, Jul 28, priced at $213 found 1 day ago
Alaska Airlines
Tue, Aug 26 - Sat, Aug 30
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$216 Roundtrip, found 13 hours ago
$216
Roundtrip
found 13 hours ago
Select Alaska Airlines flight, departing Tue, Aug 26 from Los Angeles Intl. to O'Hare Intl., returning Sat, Aug 30, priced at $216 found 13 hours ago
Frontier Airlines
Thu, Jun 5 - Wed, Jun 11
LAX
Los Angeles Intl.
MDW
Midway Intl.
$251 Roundtrip, found 2 days ago
$251
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Jun 5 from Los Angeles Intl. to Midway Intl., returning Wed, Jun 11, priced at $251 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 July, 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 $77, 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 $77 right now, why wait?

Westchester Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$90

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! (8,832 reviews)
"Beautiful, historic, great views if you select a lake view!"

Reviewed on May 26, 2025

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Congress Plaza 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
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.4/10 Very Good! (1,027 reviews)
"Def check out the rooftop view on the 17th floor. Byron was excellent for guest services on 2 occasions. Was able to check in early and walk 2 blocks to the lake. Breakfast was free but meh. Go 2 blocks West to the 3rd Coast Cafe,was reasonably priced and the food was very good."

Reviewed on May 26, 2025

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The Chicago Hotel Collection Ambassador Gold Coast
Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Stay at this 4-star family-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and valet parking (surcharge). Our guests praise ...
8/10 Very Good! (2,870 reviews)
"We stay here every time we visit Chicago. Always convenient, beds are comfy and staff is wonderful. Newly renovated too. Icing on the cake."

Reviewed on May 26, 2025

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Warwick Allerton - Chicago
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! (3,103 reviews)
"We stayed at this hotel 2 years in a row for the suenos festival and we love it every time we stay here! The staff is very kind and the walking distance was so convenient for us."

Reviewed on May 27, 2025

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citizenM Chicago Downtown
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
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! (4,201 reviews)
"Great location and close to all local attractions. Hotel was clean and comfortable. Is beginning to look a little tired but otherwise it’s a great location for all tourist areas. It can be a little noisy at night but can’t hear too much from the rooms if windows are closed."

Reviewed on May 28, 2025

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River Hotel
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
8.4/10 Very Good! (1,754 reviews)
"Good but felt like things were missing vending machines or a store where I can missing items"

Reviewed on May 23, 2025

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Fairmont Chicago at Millennium Park
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! (2,255 reviews)
"Hilton is the way to go. My wife loves shopping and all the best shops are just right around the corner. Workers here are very nice and polite."

Reviewed on May 22, 2025

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Hilton Chicago/Magnificent Mile Suites
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! (1,841 reviews)
"It was a beautiful property with great service, clean, safe and in the perfect location"

Reviewed on May 26, 2025

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InterContinental Chicago Magnificent Mile by IHG
See all 4,678 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.