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Westchester

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Westchester Flights as Low as $108

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

Frontier Airlines
Mon, Sep 28 - Mon, Oct 5
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$108 Roundtrip, found 19 hours ago
$108
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Mon, Sep 28 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Mon, Oct 5, priced at $108 found 19 hours ago
Frontier Airlines
Tue, Sep 22 - Tue, Oct 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$108 Roundtrip, found 21 hours ago
$108
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Tue, Sep 22 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $108 found 21 hours ago
Frontier Airlines
Mon, Sep 14 - Mon, Sep 14
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$113 Roundtrip, found 2 days ago
$113
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Sep 14, priced at $113 found 2 days ago
Frontier Airlines
Mon, Sep 14 - Tue, Sep 15
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 2 days ago
$118
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Mon, Sep 14 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $118 found 2 days ago
United
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 20 hours ago
$153
Roundtrip
found 20 hours ago
Select United flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 20 hours ago
Delta
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 20 hours ago
$153
Roundtrip
found 20 hours ago
Select Delta flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 20 hours ago
American Airlines
Wed, Aug 19 - Tue, Sep 8
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 20 hours ago
$153
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Wed, Aug 19 from Logan Intl. to O'Hare Intl., returning Tue, Sep 8, priced at $153 found 20 hours ago
American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$174 Roundtrip, found 6 days ago
$174
Roundtrip
found 6 days ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $174 found 6 days ago
JetBlue Airways
Sat, Jul 11 - Tue, Jul 14
BOS
Logan Intl.
ORD
O'Hare Intl.
$183 Roundtrip, found 5 days ago
$183
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Sat, Jul 11 from Logan Intl. to O'Hare Intl., returning Tue, Jul 14, priced at $183 found 5 days ago
American Airlines
Fri, Jul 24 - Fri, Jul 31
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$256 Roundtrip, found 23 hours ago
$256
Roundtrip
found 23 hours ago
Select American Airlines flight, departing Fri, Jul 24 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Jul 31, priced at $256 found 23 hours ago
Frontier Airlines
Thu, Jul 30 - Thu, Aug 20
BOS
Logan Intl.
MDW
Midway Intl.
$258 Roundtrip, found 4 days ago
$258
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Jul 30 from Logan Intl. to Midway Intl., returning Thu, Aug 20, priced at $258 found 4 days ago
Frontier Airlines
Thu, Aug 6 - Sat, Aug 15
BOI
Boise
ORD
O'Hare Intl.
$293 Roundtrip, found 2 days ago
$293
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Boise to O'Hare Intl., returning Sat, Aug 15, priced at $293 found 2 days ago
Alaska Airlines
Sat, Jul 4 - Tue, Jul 21
BOI
Boise
ORD
O'Hare Intl.
$310 Roundtrip, found 2 days ago
$310
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Sat, Jul 4 from Boise to O'Hare Intl., returning Tue, Jul 21, priced at $310 found 2 days ago
Sun Country Airlines
Thu, Aug 20 - Sun, Aug 23
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$372 Roundtrip, just found
$372
Roundtrip
just found
Select Sun Country Airlines flight, departing Thu, Aug 20 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sun, Aug 23, priced at $372 just found
Delta
Sun, Jun 28 - Wed, Jul 1
BOI
Boise
MDW
Midway Intl.
$848 Roundtrip, found 1 day ago
$848
Roundtrip
found 1 day ago
Select Delta flight, departing Sun, Jun 28 from Boise to Midway Intl., returning Wed, Jul 1, priced at $848 found 1 day ago
American Airlines
Sun, Jun 28 - Wed, Jul 1
BOI
Boise
RFD
Greater Rockford
$981 Roundtrip, found 1 day ago
$981
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sun, Jun 28 from Boise to Greater Rockford, returning Wed, Jul 1, priced at $981 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 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 $108, 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 $108 right now, why wait?

Westchester Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$108

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 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,153 reviews)
"Great location! Historic building. clean room. Good value. hallways and stairwell could use some additional care and attention. chipping paint and damaged doors."

Reviewed on Jun 21, 2026

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Congress Plaza Hotel
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 ...
9/10 Wonderful! (4,455 reviews)
"Cleaneage rooms. Great location. Lovely staff"

Reviewed on Jun 21, 2026

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Hilton Chicago/Magnificent Mile Suites
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! (1,605 reviews)
"Overall a very good hotel! Staff were friendly and helpful. The hotel is located beside Michigan Ave which gave us access to lots of shops and restaurants nearby without having to walk long distances. The view from our room was pretty good as well, giving us a look down the street. One of the concierges ..."

Reviewed on Jun 21, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,701 reviews)
"The first day there were some bumps even the lady who helped us check in was not very friendly. But the next day everything fell into place and Gabriela who checked us out was very sweet and made up for it."

Reviewed on Jun 21, 2026

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Hyatt Regency O'Hare Chicago
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 ...
8.2/10 Very Good! (1,627 reviews)
"The lobby and first floor looked nice, and the staff was friendly, but that’s where the positives ended. This was supposed to be a four-star hotel, yet it felt more like a four-star motel. The bathrooms were not very clean and had an awkward layout. There was no daily housekeeping service, and the ..."

Reviewed on Jun 21, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (2,311 reviews)
"Worn and tired room. Needs better deep cleaning and attention to chipped and damaged paint, bathroom surfaces, etc. I chose this hotel because of the free airport shuttle. Nowhere was it noted that I had to phone for pick-up. After waiting for more than 30 minutes, another hotel’s driver told me ..."

Reviewed on Jun 21, 2026

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Hilton Chicago O'Hare Airport
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (3,111 reviews)
"This is the dirtiest hotel room I have ever stayed. It was filthy. The curtains have dirty marks as large as my hand and the tissue box had something dripping and solidified on it. Everything that wasn't used was covered with dust. Hopefully I will be attaching pictures. The staff is brusque and ..."

Reviewed on Jun 21, 2026

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Freehand Chicago
Travelodge by Wyndham Downtown Chicago

Travelodge by Wyndham Downtown Chicago

2 out of 5
65 E Harrison St Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
7.6/10 Good! (2,629 reviews)
"Very old. Not many outlets in room. Window a/c. Hotel does not have own parking. Location was nice otherwise not worth value. Beds were not comfortable at all"

Reviewed on Jun 21, 2026

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Travelodge by Wyndham Downtown Chicago
See all 5,129 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.