Cheap Flights to Chester County from $127 (2026/2027)

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How Much Does it Cost To Fly To Chester County?

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

Fri, Oct 23 - Sun, Oct 25
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$254 Roundtrip, found 9 hours ago
$254
Roundtrip
found 9 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Oct 23 from O'Hare Intl. to McKellar-Sipes Regional, returning Sun, Oct 25, priced at $254 found 9 hours ago
Fri, Aug 28 - Tue, Sep 8
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$260 Roundtrip, found 9 hours ago
$260
Roundtrip
found 9 hours ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Aug 28 from O'Hare Intl. to McKellar-Sipes Regional, returning Tue, Sep 8, priced at $260 found 9 hours ago
Thu, Aug 6 - Mon, Aug 10
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$271 Roundtrip, found 5 days ago
$271
Roundtrip
found 5 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Aug 6 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Aug 10, priced at $271 found 5 days ago
Thu, Aug 6 - Mon, Aug 10
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$292 Roundtrip, found 1 day ago
$292
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Thu, Aug 6 from O'Hare Intl. to McKellar-Sipes Regional, returning Mon, Aug 10, priced at $292 found 1 day ago
Sun, Jul 26 - Tue, Aug 4
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$313 Roundtrip, found 4 days ago
$313
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Jul 26 from O'Hare Intl. to McKellar-Sipes Regional, returning Tue, Aug 4, priced at $313 found 4 days ago
Sun, Aug 2 - Thu, Aug 6
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Aug 2 from O'Hare Intl. to McKellar-Sipes Regional, returning Thu, Aug 6, priced at $324 found 1 day ago
Fri, Jul 31 - Sun, Aug 2
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$324 Roundtrip, found 2 days ago
$324
Roundtrip
found 2 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Fri, Jul 31 from O'Hare Intl. to McKellar-Sipes Regional, returning Sun, Aug 2, priced at $324 found 2 days ago
Sun, Jul 26 - Sun, Aug 2
ORD
O'Hare Intl.
MKL
McKellar-Sipes Regional
$345 Roundtrip, found 4 days ago
$345
Roundtrip
found 4 days ago
Select KEY LIME AIR DBA DENVER AIR CONNECTION flight, departing Sun, Jul 26 from O'Hare Intl. to McKellar-Sipes Regional, returning Sun, Aug 2, priced at $345 found 4 days ago
OriginDestinationTravel DatesFlights From*
TPAJacksonJuly 25 to July 27$855
*Prices include taxes and fees

Best Chester County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Rama Inn Bells
2.0-star property

Rama Inn Bells

Aug 20 - Aug 24

4 night stay

Philadelphia (PHL) to Jackson (MKL)

American Airlines • Non-stop • Coach

Jackson (MKL) to Philadelphia (PHL)

Denver Air Connection • Non-stop • Coach
Price was $660, price is now $619 per person
$619
per person
found 13 hours ago
Green Frog Farm Cabins
2.0-star property

Green Frog Farm Cabins

Aug 20 - Aug 24

4 night stay

Philadelphia (PHL) to Jackson (MKL)

American Airlines • Non-stop • Coach

Jackson (MKL) to Philadelphia (PHL)

Denver Air Connection • Non-stop • Coach
Price was $977, price is now $923 per person
$923
per person
found 13 hours ago
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Travelers ❤️ These Chester County 🏨

Americana Inn

Americana Inn

2.5 out of 5
550 Sanford St Henderson TN
Stay at this motel in Henderson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Henderson Wi-Fi Park and Black Box Theatre are located nearby.
7.6/10 Good! (385 reviews)
"The building itself shows its age. Some repairs in the room were not done well. However the room was clean. The continental breakfast was lacking but not a big deal to us. We did like how well lit the outside is at night. Makes you feel much more safe if you must go out late at night."

Reviewed on Jul 3, 2026

Opens in a new windowAmericana Inn
Sleep Inn & Suites Savannah Tennessee Riverfront

Sleep Inn & Suites Savannah Tennessee Riverfront

2.5 out of 5
105 Million Dollar Way Savannah TN
Book a stay at this business-friendly hotel in Savannah. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Riverside City Park and Cherry Mansion are located nearby.
9.2/10 Wonderful! (50 reviews)
"A great place all around. 10/10 would recommend! The pool is fantastic. It over looks the water and as the pool water spills over the sides it sounds like waves hitting a shoreline. The swim up bar is a plus. There's a park right next to the property, which is nice to explore. A good place to unwind. ..."

Reviewed on Jul 19, 2026

Opens in a new windowSleep Inn & Suites Savannah Tennessee Riverfront
Best Western Plus Executive Residency Jackson Northeast

Best Western Plus Executive Residency Jackson Northeast

3 out of 5
2443 CHRISTMASVILLE COVE Jackson TN
Book a stay at this business-friendly hotel in Jackson. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions West Tennessee Healthcare Sportsplex and The Ballpark at Jackson are located nearby.
Opens in a new windowBest Western Plus Executive Residency Jackson Northeast
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WoodSpring Suites Jackson Hub City

WoodSpring Suites Jackson Hub City

2.5 out of 5
19 BINK DRIVE Jackson TN
Stay at this hotel in Jackson. Enjoy free WiFi, free parking, and a fitness center. Popular attractions West Tennessee Healthcare Sportsplex and The Ballpark at Jackson are located nearby.
8/10 Very Good! (390 reviews)
"Great service friendly staff very helpful"

Reviewed on Jul 19, 2026

Opens in a new windowWoodSpring Suites Jackson Hub City
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.

Frequently asked questions

How much is the cheapest flight to Chester County?
To give you a figure to work with, the cheapest roundtrip flight to Chester County cost $254 during the last seven days. An excellent way to nab a travel bargain is to be flexible with your dates. This price was available on Travelocity for flights to Chester County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Chester County?
Pack your suitcase and head off with one of the 15 airlines that operate flights to Chester County. Secure a seat with the popular carrier, American Airlines. It operates around 658 flights each month to Henderson, Chester County's gateway city, so finding a fare that suits should be a snap.
What is the cheapest month to fly to Chester County?
If you have your heart set on a vacation in Chester County, October is the cheapest time to fly there. This is according to Travelocity's direct return flight demand between January and December last year. Work out your ideal dates and secure your spot today.
How can I check my flight status to Chester County?
Go to the Travelocity customer portal, Trips. You'll find all things related to your flight to Chester County here, including valuable information about your flight status, gate changes and more. Keep an eye out for Trips at the top of the Travelocity homepage. Create your free account and find the answers you're after. You can also access your itinerary on the move and get real-time trip notifications through the Travelocity app. You'll find all your itineraries in one place, so it's easy to share details with any members of your family flying with you.
How do I find the best deals on flights to Chester County?
Be flexible with your travel dates and there's a good chance you'll find a sensational deal. After you've searched for flights on Travelocity, click the "Flexible dates" box at the top of the page to compare prices with nearby days. Also try to book ahead of schedule and avoid peak periods. In the last seven days, the lowest price for a roundtrip flight to Chester County was $254. This price was available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
Why should I book my flight to Chester County with Travelocity?
If you're chasing cheap flights to Chester County, you'll find some top deals with Travelocity. From cheap family flights with low-cost air carriers to flexible fares, we're here for you all the way. Experience a stress-free vacation with our round-the-clock online chat support, Price Match Guarantee and free cancellations with most hotels. Start planning your schedule and get ready to jump on a plane to this vibrant destination.
How much is a flight to Chester County on average?
Roundtrip flights to Chester County were priced between $254 and $855 in the last seven days. When you find a ticket price you like, grab it quickly. Cheap deals don't stick around forever! These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Chester County?
If you have a long-haul flight to Chester County, you can usually expect meals, drinks and entertainment on board. Airlines endeavor to make longer flights as pleasant as possible. Shorter journeys — along with flights offered by low-cost airlines — may not have such inclusions. If you're looking for cheap flights for family vacations with a low-cost carrier, it's possible you'll pay extra for meals and entertainment.