Cheap Flights To Chester 2025

Photo by Elizabeth Massa Peroulakis

Chester Flights as Low as $107

These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Thu, Jun 12 - Sat, Jun 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$107 Roundtrip, found 5 days ago
$107
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jun 12 from Orlando Intl. to Bradley Intl., returning Sat, Jun 21, priced at $107 found 5 days ago
Frontier Airlines
Mon, Jun 9 - Sat, Jun 21
MCO
Orlando Intl.
BDL
Bradley Intl.
$125 Roundtrip, found 5 days ago
$125
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Mon, Jun 9 from Orlando Intl. to Bradley Intl., returning Sat, Jun 21, priced at $125 found 5 days ago
Breeze Airways
Wed, Jun 11 - Wed, Jun 18
MCO
Orlando Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 5 days ago
$132
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Wed, Jun 11 from Orlando Intl. to Bradley Intl., returning Wed, Jun 18, priced at $132 found 5 days ago
Frontier Airlines
Thu, Jun 12 - Fri, Jun 20
MCO
Orlando Intl.
BDL
Bradley Intl.
$138 Roundtrip, found 5 days ago
$138
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Thu, Jun 12 from Orlando Intl. to Bradley Intl., returning Fri, Jun 20, priced at $138 found 5 days ago
Frontier Airlines
Fri, Jun 20 - Fri, Jun 27
MCO
Orlando Intl.
BDL
Bradley Intl.
$150 Roundtrip, found 2 days ago
$150
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Fri, Jun 20 from Orlando Intl. to Bradley Intl., returning Fri, Jun 27, priced at $150 found 2 days ago
Spirit Airlines
Wed, Jun 11 - Wed, Jun 18
MCO
Orlando Intl.
BDL
Bradley Intl.
$152 Roundtrip, found 5 days ago
$152
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Wed, Jun 11 from Orlando Intl. to Bradley Intl., returning Wed, Jun 18, priced at $152 found 5 days ago
Breeze Airways
Thu, Aug 28 - Mon, Sep 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$154 Roundtrip, found 6 days ago
$154
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Mon, Sep 1, priced at $154 found 6 days ago
Frontier Airlines
Sat, May 17 - Sat, May 24
PHX
Sky Harbor Intl.
BDL
Bradley Intl.
$208 Roundtrip, found 3 days ago
$208
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, May 17 from Sky Harbor Intl. to Bradley Intl., returning Sat, May 24, priced at $208 found 3 days ago
Frontier Airlines
Fri, May 9 - Sat, May 17
LAS
Harry Reid Intl.
BDL
Bradley Intl.
$220 Roundtrip, found 16 hours ago
$220
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Fri, May 9 from Harry Reid Intl. to Bradley Intl., returning Sat, May 17, priced at $220 found 16 hours ago
United
Sat, Jul 26 - Sat, Jul 26
MCO
Orlando Intl.
BDL
Bradley Intl.
$237 Roundtrip, found 16 hours ago
$237
Roundtrip
found 16 hours ago
Select United flight, departing Sat, Jul 26 from Orlando Intl. to Bradley Intl., returning Sat, Jul 26, priced at $237 found 16 hours ago
American Airlines
Sat, Jul 26 - Sat, Jul 26
MCO
Orlando Intl.
BDL
Bradley Intl.
$237 Roundtrip, found 16 hours ago
$237
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Sat, Jul 26 from Orlando Intl. to Bradley Intl., returning Sat, Jul 26, priced at $237 found 16 hours ago
JetBlue Airways
Fri, Nov 21 - Mon, Nov 24
MCO
Orlando Intl.
BDL
Bradley Intl.
$247 Roundtrip, found 11 hours ago
$247
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Fri, Nov 21 from Orlando Intl. to Bradley Intl., returning Mon, Nov 24, priced at $247 found 11 hours ago
Delta
Tue, Jun 24 - Sun, Jun 29
MCO
Orlando Intl.
BDL
Bradley Intl.
$257 Roundtrip, found 2 days ago
$257
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Jun 24 from Orlando Intl. to Bradley Intl., returning Sun, Jun 29, priced at $257 found 2 days ago
Delta
Tue, Jun 10 - Tue, Jun 17
HSV
Huntsville Intl.
BDL
Bradley Intl.
$259 Roundtrip, found 16 hours ago
$259
Roundtrip
found 16 hours ago
Select Delta flight, departing Tue, Jun 10 from Huntsville Intl. to Bradley Intl., returning Tue, Jun 17, priced at $259 found 16 hours ago
United
Wed, Jun 4 - Wed, Jun 11
BTM
Bert Mooney
BDL
Bradley Intl.
$349 Roundtrip, found 1 day ago
$349
Roundtrip
found 1 day ago
Select United flight, departing Wed, Jun 4 from Bert Mooney to Bradley Intl., returning Wed, Jun 11, priced at $349 found 1 day ago
Delta
Wed, May 7 - Sat, May 10
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$354 Roundtrip, found 13 hours ago
$354
Roundtrip
found 13 hours ago
Select Delta flight, departing Wed, May 7 from Ronald Reagan Washington National to Bradley Intl., returning Sat, May 10, priced at $354 found 13 hours ago

Flight Travel Guide to Chester

If you feel like Chester is calling your name, then book a flight to (airport). And with the AARP Travel Center Powered by Expedia®, can become a reality sooner than you think. AARP Travel combines their members-only discount with the best rates from Expedia, giving members the best price in travel, guaranteed.

As an AARP member, you'll get exclusive rates on:

  • Hotels
  • Car rentals
  • Flights
  • Waived booking fees on flights

Once you have entered your destination and departure point, we will show you a full list of deals for your route. Don't forget to look at flights to alternative airports nearby, which can help you get a lower rate.

Airport Transportation

Once you have reserved plane tickets to Chester with AARP Travel, you may want to book a car so you can get around on your own. You can request Chester car rentals under our cars tab and hop in the driver's seat as soon as you step out of the airport. If you'd prefer public transportation, check out the Metropolitan Transit System bus, or if there's trolleys or Amtrak stations nearby.

Chester Activities

Not sure where to start? Not to worry—there's so many things to do in this city. Chester has so much to do, and we can help you get started.

If you're looking for some fun activities to do in Chester, make sure you look at our "Things to Do in Chester" page for activities and excursions for the whole crew.

Book Your Hotel in Chester

Chester has hotel to choose from, make sure you check out our hotel listings tab for some great recommendations from past visitors. No matter where you stay, just remember that you'll get the best price out there when you book with AARP Travel.

Book Your Chester Trip Now

Once you've decided when you want to visit, allow us here at AARP Travel to connect you with inexpensive tickets to Chester. There is no better time than now to start booking your next trip. Book one of our flights today.