Cheap Flights to Windham County from $62 (2026/2027)

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A grassy field with cows grazing, a clear sky, and distant hills.

Plainfield

Flights
Plainfield
A church with a steeple, a bridge, and a bench in a park.

Willimantic

Flights
Willimantic

How Much Does it Cost To Fly To Windham County?

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

Sat, Aug 29 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$133 Roundtrip, found 5 days ago
$133
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $133 found 5 days ago
Sat, Aug 29 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 5 days ago
$137
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Aug 29 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $137 found 5 days ago
Thu, Sep 10 - Wed, Sep 16
TPA
Tampa Intl.
PVD
T.F. Green
$137 Roundtrip, found 20 hours ago
$137
Roundtrip
found 20 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Tampa Intl. to T.F. Green, returning Wed, Sep 16, priced at $137 found 20 hours ago
Wed, Aug 26 - Tue, Sep 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$138 Roundtrip, found 1 day ago
$138
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Orlando Intl. to Bradley Intl., returning Tue, Sep 1, priced at $138 found 1 day ago
Wed, Aug 26 - Tue, Sep 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$140 Roundtrip, found 23 hours ago
$140
Roundtrip
found 23 hours ago
Select Breeze Airways flight, departing Wed, Aug 26 from Orlando Intl. to Bradley Intl., returning Tue, Sep 1, priced at $140 found 23 hours ago
Tue, Sep 1 - Mon, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$141 Roundtrip, found 5 days ago
$141
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Sep 1 from Orlando Intl. to Bradley Intl., returning Mon, Sep 7, priced at $141 found 5 days ago
Sat, Sep 5 - Sun, Sep 13
TPA
Tampa Intl.
BDL
Bradley Intl.
$151 Roundtrip, found 2 hours ago
$151
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Sep 5 from Tampa Intl. to Bradley Intl., returning Sun, Sep 13, priced at $151 found 2 hours ago
Thu, Aug 27 - Wed, Sep 2
MCO
Orlando Intl.
PVD
T.F. Green
$165 Roundtrip, just found
$165
Roundtrip
just found
Select Breeze Airways flight, departing Thu, Aug 27 from Orlando Intl. to T.F. Green, returning Wed, Sep 2, priced at $165 just found
OriginDestinationTravel DatesFlights From*
LAXWarwickAugust 26 to August 30$215
LAXWindsor LocksSeptember 2 to September 6$220
LAXWorcesterAugust 6 to August 10$299
PDXWarwickSeptember 25 to October 3$307
PDXWindsor LocksAugust 5 to August 12$390
HKGWindsor LocksAugust 17 to August 24$1,570
CANWarwickJuly 22 to July 26$1,609
HKGWarwickAugust 14 to August 21$1,801
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
LAXWindsor LocksJuly 12 to August 6$376
LAXWarwickJuly 10 to July 13$416
PDXWindsor LocksJuly 12 to July 16$493
PDXWarwickJuly 10 to July 21$525
PVGWindsor LocksJuly 12 to July 13$2,175
*Prices include taxes and fees

Best Windham County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Fox Point Landing Residences
4.0-star property

Fox Point Landing Residences

Aug 25 - Aug 30

5 night stay

Jacksonville (JAX) to Providence (PVD)

American Airlines • Non-stop • Coach

Providence (PVD) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,387, price is now $1,021 per person
$1,021
per person
found 1 hour ago
Wayfinder Newport
4.0-star property

Wayfinder Newport

Aug 25 - Aug 30

5 night stay

Jacksonville (JAX) to Providence (PVD)

American Airlines • Non-stop • Coach

Providence (PVD) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $2,357, price is now $1,512 per person
$1,512
per person
found 1 hour ago
Holiday Inn Express Newport North - Middletown by IHG
2.5-star property

Holiday Inn Express Newport North - Middletown by IHG

Aug 25 - Aug 30

5 night stay

Jacksonville (JAX) to Providence (PVD)

American Airlines • Non-stop • Coach

Providence (PVD) to Jacksonville (JAX)

Southwest Airlines • Non-stop • Coach
Save 100% on your flight
Price was $1,533, price is now $1,144 per person
$1,144
per person
found 1 hour ago
Don't see what you're looking for?
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Travelers ❤️ These Windham County 🏨

Best Western Mystic Hotel

Best Western Mystic Hotel

2.5 out of 5
48 Whitehall Ave Mystic CT
Book a stay at this business-friendly hotel in Mystic. Enjoy free parking, an outdoor pool, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Olde Mistick Village and Mystic Aquarium and Institute for Exploration are located nearby.
8.6/10 Excellent! (604 reviews)
"Pictures are nothing like the actual rooms you'll be staying in. There was black mold growing on cheap tiled ceilings. The air conditioner wasn't working correctly and the whole room had a layer of moisture on everything including the worn down carpet and the bed sheets/pillows. The bathrooms are ..."

Reviewed on Jul 6, 2026

Opens in a new windowBest Western Mystic Hotel
Hilltop Inn and Suites, near Foxwoods Casino

Hilltop Inn and Suites, near Foxwoods Casino

2.5 out of 5
373 Norwich Westerly Rd North Stonington CT
Stay at this hotel in North Stonington. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
8/10 Very Good! (2,789 reviews)
"Coffee ran out at breakfast, no one at desk to advise, finally able to tell cleaning person who got the desk attendant. No hot water in shower, advised staff never got fixed. Have been going there for several years on 7/4 weekend, this is last time. Will find someplace else next year"

Reviewed on Jul 6, 2026

Opens in a new windowHilltop Inn and Suites, near Foxwoods Casino
Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Book a stay at this business-friendly hotel in Mashantucket. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
8.4/10 Very Good! (51 reviews)
"Best pillows and bed, had a wonderful sleep"

Reviewed on Jul 6, 2026

Opens in a new windowTwo Trees Inn
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The Fox Tower at Foxwoods

The Fox Tower at Foxwoods

3.5 out of 5
350 Trolley Line Blvd Mashantucket CT
Book a stay at this spa hotel in Mashantucket. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Foxwoods Resort Casino and Grand Theater at Foxwoods Resort Casino are located nearby.
8.6/10 Excellent! (1,091 reviews)
"Great stay"

Reviewed on Jun 23, 2026

Opens in a new windowThe Fox Tower at Foxwoods
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 Windham County?
A roundtrip flight to Windham County cost as little as $133 during the last seven days. Once you've chosen your travel dates, we'll help you snap up an awesome deal. This price was available on Travelocity for flights to Windham County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Windham County?
You'll have a choice of 15 airline companies when you want to lock in your flight to Windham County. Let American Airlines help you on your way. This leading carrier has 385 services every month to Plainfield, Windham County's major city.
What is the cheapest month to fly to Windham County?
For the best chance at nabbing a fantastic flight deal, time your escape sometime during August. Based on Travelocity's direct flight demand between January and December last year, it's the cheapest period to jet to Windham County.
How can I check my flight status to Windham County?
There are a couple of ways to track your flight status. You can find all the necessary details in our Trips portal, which is located at the top right of our homepage. Sign in or create an account — you can then browse and amend your bookings whenever you want to. If you're already on the move, the Travelocity app can also help you look up the status of your flight to Windham County, as well as share details with any members of your family flying with you.
How do I find the best deals on flights to Windham County?
Be flexible with your dates and there's a strong chance you'll find a deal you can't pass up. When searching for flights on Travelocity, click the "Flexible dates" feature above your results to reveal prices for nearby days. Also try to book ahead and avoid peak periods. In the last seven days, the best price for a roundtrip flight to Windham County was $133. 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 Windham County with Travelocity?
From cheap family flights to all-inclusive resorts and activities, Travelocity has got you covered for incredible adventures. With everything you need in one place, you can enjoy more time daydreaming about all the cool things you'll be doing in Windham County and less time planning. Plus with our Price Match Guarantee and online chat support, our mission is to make your next break a fabulous one.
What are the most popular flight routes to Windham County?
If you're planning to jump on a flight to Windham County, here are a few of the most popular routes that'll get you there:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 1,131 flights a month.
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 1,048 flights a month.
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 866 flights a month.

How much is a flight to Windham County on average?
Based on prices found on Travelocity over the last seven days, roundtrip flights to Windham County were between $133 and $2,175. Whenever you're ready to go, Travelocity will help you find a fare that'll suit your budget. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
How long is the average flight to Windham County?
Where you fly out from will usually determine how much time your direct flight to Windham County will take. Here are some of the most popular routes to Windham County and their average journey times:

  • Atlanta, GA (ATL-Hartsfield-Jackson Atlanta Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 15 minutes
  • Chicago, IL (ORD-O'Hare Intl.) to Bradley Intl. Airport (BDL) - 2 hours and 9 minutes
  • Philadelphia, PA (PHL-Philadelphia Intl.) to Bradley Intl. Airport (BDL) - 1 hour and 12 minutes

What can I expect on a flight to Windham County?
The flight time and whether you fly with a budget or full-service airline will determine what you can expect. If you're searching for long-haul flights to Windham County, entertainment and food will come standard. Interested in cheap flights for family vacations? Check out the fares with low-cost carriers. Typically, these airlines don't come with as many inclusions, so be prepared to pay for your drinks and meals.