Cheap Flights to Windham County from $63 (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.

Fri, Jan 8 - Mon, Jan 11
FLL
Fort Lauderdale - Hollywood Intl.
PVD
T.F. Green
$144 Roundtrip, found 14 hours ago
$144
Roundtrip
found 14 hours ago
Select Breeze Airways flight, departing Fri, Jan 8 from Fort Lauderdale - Hollywood Intl. to T.F. Green, returning Mon, Jan 11, priced at $144 found 14 hours ago
Thu, Sep 10 - Sat, Sep 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$145 Roundtrip, found 2 days ago
$145
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Sat, Sep 12, priced at $145 found 2 days ago
Thu, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$149 Roundtrip, found 3 hours ago
$149
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Mon, Sep 14, priced at $149 found 3 hours ago
Thu, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$149 Roundtrip, found 3 hours ago
$149
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Mon, Sep 14, priced at $149 found 3 hours ago
Sat, Sep 26 - Thu, Oct 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$153 Roundtrip, found 1 day ago
$153
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Sep 26 from Orlando Intl. to Bradley Intl., returning Thu, Oct 1, priced at $153 found 1 day ago
Fri, Nov 13 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$155 Roundtrip, just found
$155
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Nov 13 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $155 just found
Fri, Sep 11 - Mon, Oct 5
MCO
Orlando Intl.
PVD
T.F. Green
$166 Roundtrip, found 5 days ago
$166
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Sep 11 from Orlando Intl. to T.F. Green, returning Mon, Oct 5, priced at $166 found 5 days ago
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
BDL
Bradley Intl.
$243 Roundtrip, found 20 hours ago
$243
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Thu, Nov 12 from Orlando Intl. to Bradley Intl., returning Mon, Nov 16, priced at $243 found 20 hours ago
OriginDestinationTravel DatesFlights From*
LAXWindsor LocksSeptember 26 to October 3$259
LAXWarwickSeptember 8 to September 19$311
PDXWarwickOctober 3 to October 10$331
PDXWindsor LocksSeptember 9 to September 15$342
LAXWorcesterSeptember 10 to September 17$461
PDXWorcesterSeptember 17 to September 20$518
HKGWindsor LocksSeptember 14 to September 21$1,345
PVGWarwickOctober 1 to October 6$1,433
PVGWindsor LocksNovember 12 to November 23$1,444
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
LAXWarwickAugust 29 to September 4$395
LAXWindsor LocksAugust 29 to August 31$493
*Prices include taxes and fees

Best Windham County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Cottage Inn At Amos Lake
3.0-star property

The Cottage Inn At Amos Lake

Oct 3 - Oct 9

6 night stay

Chicago (ORD) to Providence (PVD)

American Airlines • Coach

Providence (PVD) to Chicago (ORD)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,102, price is now $810 per person
$810
per person
found 20 hours ago
Fox Point Landing Residences
4.0-star property

Fox Point Landing Residences

Oct 28 - Nov 3

6 night stay

Nashville (BNA) to Providence (PVD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,350, price is now $941 per person
$941
per person
found 22 hours ago
Club Wyndham Newport Onshore
3.0-star property

Club Wyndham Newport Onshore

Sep 11 - Sep 14

3 night stay

Denver (DEN) to Providence (PVD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,804, price is now $1,346 per person
$1,346
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Windham County
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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! (714 reviews)
"Everything from booking, checking in to checking out was great. All of the staff are kind and helpful. Breakfast was plentiful with a variety of choices. My dog loved her stay as well! I would stay here again and I do recommend Best Western near olde mystic village to anyone."

Reviewed on Aug 24, 2026

Opens in a new windowBest Western Mystic Hotel
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.
Opens in a new windowTwo Trees Inn
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.
7.8/10 Good! (2,877 reviews)
"Passing through down 95 and needed a place to lay our heads. Room is very basic but very clean with all one could need."

Reviewed on Aug 24, 2026

Opens in a new windowHilltop Inn and Suites, near Foxwoods Casino
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Spark by Hilton Mystic Groton

Spark by Hilton Mystic Groton

3 out of 5
55 Whitehall Avenue Mystic CT
Stay at this hotel in Mystic. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Olde Mistick Village and Mystic Aquarium and Institute for Exploration are located nearby.
Opens in a new windowSpark by Hilton Mystic Groton
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 $144 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 January. 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 $144. 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 $144 and $1,444. 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.