$50 Cheap flights to Windham County

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Cheap flights to Windham County from $50 One Way, $98 Round Trip

$98 return flights and $50 one-way flights to Windham County were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Thu, Sep 17 - Sun, Sep 27
MCO
Orlando
BDL
Hartford
$98 Roundtrip, just found
$98
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Sep 17 from Orlando to Hartford, returning Sun, Sep 27, priced at $98 just found
Thu, Sep 10 - Sun, Sep 13
MCO
Orlando
BDL
Hartford
$100 Roundtrip, found 2 hours ago
$100
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Sep 10 from Orlando to Hartford, returning Sun, Sep 13, priced at $100 found 2 hours ago
Fri, Jan 22 - Mon, Jan 25
TPA
Tampa
PVD
Providence
$132 Roundtrip, found 3 days ago
$132
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Fri, Jan 22 from Tampa to Providence, returning Mon, Jan 25, priced at $132 found 3 days ago
Sat, Sep 5 - Thu, Sep 17
TPA
Tampa
BDL
Hartford
$144 Roundtrip, found 2 days ago
$144
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 5 from Tampa to Hartford, returning Thu, Sep 17, priced at $144 found 2 days ago
Sat, Aug 29 - Wed, Sep 2
FLL
Fort Lauderdale
BDL
Hartford
$160 Roundtrip, found 6 hours ago
$160
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Sat, Aug 29 from Fort Lauderdale to Hartford, returning Wed, Sep 2, priced at $160 found 6 hours ago
Wed, Sep 9 - Sat, Sep 12
FLL
Fort Lauderdale
PVD
Providence
$160 Roundtrip, found 2 days ago
$160
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Sep 9 from Fort Lauderdale to Providence, returning Sat, Sep 12, priced at $160 found 2 days ago
Thu, Sep 17 - Tue, Sep 22
MCO
Orlando
PVD
Providence
$162 Roundtrip, found 3 hours ago
$162
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Sep 17 from Orlando to Providence, returning Tue, Sep 22, priced at $162 found 3 hours ago
Tue, Oct 6 - Tue, Oct 6
MCO
Orlando
PVD
Providence
$207 Roundtrip, found 1 day ago
$207
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Oct 6 from Orlando to Providence, returning Tue, Oct 6, priced at $207 found 1 day ago
Sat, Sep 12 - Sat, Sep 19
FLL
Fort Lauderdale
ORH
Worcester
$266 Roundtrip, found 2 days ago
$266
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Sat, Sep 12 from Fort Lauderdale to Worcester, returning Sat, Sep 19, priced at $266 found 2 days ago
Thu, Sep 3 - Sun, Sep 6
FLL
Fort Lauderdale
BDL
Hartford
$270 Roundtrip, found 4 days ago
$270
Roundtrip
found 4 days ago
Select American Airlines flight, departing Thu, Sep 3 from Fort Lauderdale to Hartford, returning Sun, Sep 6, priced at $270 found 4 days ago
Sat, Sep 19 - Wed, Sep 23
FLL
Fort Lauderdale
PVD
Providence
$281 Roundtrip, found 3 days ago
$281
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 19 from Fort Lauderdale to Providence, returning Wed, Sep 23, priced at $281 found 3 days ago
Sat, Sep 26 - Tue, Sep 29
FLL
Fort Lauderdale
PVD
Providence
$281 Roundtrip, found 3 days ago
$281
Roundtrip
found 3 days ago
Select Delta flight, departing Sat, Sep 26 from Fort Lauderdale to Providence, returning Tue, Sep 29, priced at $281 found 3 days ago

Deals For This Weekend's Flights

OriginDestinationTravel DatesFlights From*
LAXWarwickAugust 14 to August 17$323
LAXWindsor LocksAugust 15 to September 14$425
PDXWindsor LocksAugust 15 to August 22$500
PDXWarwickAugust 14 to August 17$943
*Prices include taxes and fees

Find The Perfect Hotel For After Your Flight

Score Epic Windham County Accommodation Deals

Best Western Mystic Hotel

Best Western Mystic Hotel

2.5 out of 5
48 Whitehall Ave Mystic CT
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $158 total per night from Aug 23 to Aug 24
$158 total
Aug 23 - Aug 24
Total with taxes and fees
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 ...
Opens in a new windowBest Western Mystic Hotel
Two Trees Inn

Two Trees Inn

2.5 out of 5
240 Indiantown Rd Mashantucket CT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Aug 11 to Aug 12
$123 total
Aug 11 - Aug 12
Total with taxes and fees
Book a stay at this business-friendly hotel in Mashantucket. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Foxwoods Resort Casino and ...
8.4/10 Very Good! (176 reviews)
"Clean room, well kept. Quiet."

Reviewed on Aug 7, 2026

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
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $113 total per night from Aug 16 to Aug 17
$113 total
Aug 16 - Aug 17
Total with taxes and fees
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 ...
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
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $150 total per night from Sep 7 to Sep 8
$150 total
Sep 7 - Sep 8
Total with taxes and fees
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 ...
8.4/10 Very Good! (1,817 reviews)
"Good location and mainly clean"

Reviewed on Aug 7, 2026

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.

Need a Car For After Your Flight?

Economy

Chevrolet Spark
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass
  • 5 people
Jeep Compass
SUV Jeep Compass

Windham County

Orbitz is your one stop for guaranteed low prices on Windham County flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

Save Big On Car Rentals Too

Orbitz will find you discount air fare for flights to Windham County and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Windham County Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

Book Travel on the Fly with Orbitz on the Go

Our state of the art mobile apps will allow you to book cheap flights to Windham County from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

Frequently asked questions

Which airlines fly to Windham County?
Make sure you have a valid passport and select from the 24 airlines offering flights to Bradley Intl. Airport (BDL). After exiting the plane, Windham County is yours to discover. Search for the best deals from these leading carriers:

  • Air Canada - 17 flights to Windham County per month
  • JetBlue - 16 flights to Windham County per month

How much is a flight to Windham County?
Travelers from near and far landed round-trip flight deals ranging between $98 and $943 this week. Kicking off your trip from Orlando (MCO)? The most affordable one-way prices started at just $50.
How to book the cheapest flight to Windham County?
With Orbitz, you'll find some of the most incredible flight deals around from a great range of airlines. But if you'd like to increase your likelihood of booking cheap flights to Windham County, here are some suggestions designed to help:

  • Consider alternative airports for a cheaper fare. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will list the available options.
  • If you're flexible with your plans, click on the 'Show flexible dates' link. It'll bring up flight deals for the days around your chosen departure. Fares often vary depending on what day it is.
  • To refine your results, click on 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also choose your preferred departure and arrival times under 'Sort & Filter' to the left.
  • The early bird catches the most rewarding deals, so book as soon as you know your travel dates. The cheapest fares are quick to sell out and prices normally increase as the departure date gets closer.
  • Save loads on your vacation by combining your flights, hotels and car rental into an Orbitz package. Your wallet will thank you for it.
  • If you can, don't fly in the most popular seasons. Airfares surge during summer, school breaks and other vacation periods like Easter and Christmas.

What is the best time to book a flight to Windham County?
Generally speaking, the cheapest month to reserve a plane ticket is January. This is followed by February then August. When searching for a cheap flight to Windham County, be ready to book. Cheap deals appear in an instant and don't wait around!
What day of the week is the cheapest to book a flight to Windham County?
To score an unbeatable flight deal, make a booking on a Tuesday, Wednesday or Saturday. Usually, these are the cheapest days to purchase airfares to Windham County.
What is the cheapest day of the week to fly to Windham County?
If you're chasing cheap flights to Windham County, depart early in the week. Orbitz data from 2020 shows Monday is the most affordable day to travel, followed by Tuesday. Saturday has the most expensive fares, so avoid flying on this day and do your bank account a favor.
What is the cheapest month to fly to Windham County?
Fly during August if you're on a budget. Orbitz data has found that it's generally the best month for cheap flights to Windham County. June is when ticket prices are at their most expensive.
Which airlines allow free cancellation?
Plans change, and we believe your ticket should be able to as well. That's why Orbitz makes it a cinch to search for fares with no change fees and free cancellation. Just enter your travel details and then select "Filter by flexible change policies." How's that for fuss-free?
What do I need for the flight to Windham County?
There's so much to sort out for any big adventure, so it's useful to get a bit of help along the way. Here's a handy checklist to ensure you're organized for take off:

  • Make sure you've got your travel paperwork and some identification. For international journeys, you'll need to take your passport. When booking your tickets, always use the same name, gender and birth date as indicated on your government-issued ID.
  • A well-packed carry-on bag is just the ticket for a comfortable flight experience. Given this journey to Windham County is no short hop, take a few snacks and activities to keep you happy. Something to read is sure to help the hours pass.
  • No matter what the season is at your destination, plane cabins (and airports) can get quite cool. Take an extra layer on your journey to stay warm and comfy.

How do I get cheap first-class/business deals to Windham County?
If you think a first or business-class ticket is beyond your grasp, think again. Here are some terrific tips to help you nab a premium flight to Windham County for less:

  • Be flexible with your travel dates and wait for early bird or last-minute sales on business or first-class airfares.
  • Look for a low-cost airline that offers seats in business class. They often come with extra legroom and a glass of bubbly — and a more attractive price.
  • Bid for an upgrade in online auctions or upgrade your fare with your frequent flyer points.

What is the best time to go to Windham County?
If you'd like to soak up the atmosphere of Windham County in the tourist season, May, June and July are the best months to visit. June 20 signals the beginning of summer in the Northern Hemisphere and is a wonderful time to travel if you savor the great outdoors. During this time of year, average daily temperatures range from 60 ºF to 80 ºF.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.