Cheap Flights to Tolland County from $42 (2026/2027)

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Flights
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How Much Does it Cost To Fly To Tolland County?

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

Wed, Nov 11 - Sat, Nov 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$63 Roundtrip, found 1 day ago
$63
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Bradley Intl., returning Sat, Nov 14, priced at $63 found 1 day ago
Fri, Oct 30 - Mon, Nov 9
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$69 Roundtrip, found 1 day ago
$69
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 30 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 9, priced at $69 found 1 day ago
Fri, Dec 11 - Mon, Dec 14
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$71 Roundtrip, found 1 day ago
$71
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 11 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Dec 14, priced at $71 found 1 day ago
Sat, Nov 7 - Wed, Nov 11
TPA
Tampa Intl.
BDL
Bradley Intl.
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Nov 7 from Tampa Intl. to Bradley Intl., returning Wed, Nov 11, priced at $74 found 1 day ago
Fri, Oct 30 - Mon, Nov 9
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$76 Roundtrip, found 1 day ago
$76
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 30 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 9, priced at $76 found 1 day ago
Fri, Dec 11 - Mon, Dec 14
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$78 Roundtrip, found 1 day ago
$78
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 11 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Dec 14, priced at $78 found 1 day ago
Fri, Dec 11 - Mon, Dec 14
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 1 day ago
$100
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Dec 11 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Dec 14, priced at $100 found 1 day ago
Sat, Dec 5 - Sat, Dec 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$230 Roundtrip, found 3 days ago
$230
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Dec 12, priced at $230 found 3 days ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$235 Roundtrip, found 16 hours ago
$235
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $235 found 16 hours ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$235 Roundtrip, found 16 hours ago
$235
Roundtrip
found 16 hours ago
Select American Airlines flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $235 found 16 hours ago
OriginDestinationTravel DatesFlights From*
LAXWindsor LocksDecember 9 to December 12$239
PDXWindsor LocksDecember 15 to December 16$272
LAXWorcesterDecember 5 to December 12$514
PVGWindsor LocksDecember 3 to December 10$1,381
HKGWindsor LocksNovember 6 to November 10$1,481
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
PDXWindsor LocksOctober 25 to October 28$670
LAXWindsor LocksOctober 23 to October 26$676
HKGWindsor LocksOctober 25 to October 30$1,817
*Prices include taxes and fees

Best Tolland County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
2.0-star property

Pier Blue Inn Old Saybrook - Essex

Dec 3 - Dec 7

4 night stay

Chicago (ORD) to New Haven (HVN)

Delta • Roundtrip • Coach
Price was $489, price is now $416 per person
$416
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Oct 28 - Nov 1

4 night stay

San Diego (SAN) to New Haven (HVN)

Alaska Airlines • Roundtrip • Coach
Price was $3,562, price is now $1,795 per person
$1,795
per person
found 12 hours ago
Head of Pond House
3.0-star property

Head of Pond House

Dec 3 - Dec 7

4 night stay

Chicago (ORD) to New Haven (HVN)

Delta • Roundtrip • Coach
Price was $1,007, price is now $943 per person
$943
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Chicago to Tolland County
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Travelers ❤️ These Tolland County 🏨

Inn on Storrs

Inn on Storrs

3.5 out of 5
123 Storrs Road Willimantic CT
Book a stay at this business-friendly motel in Willimantic. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions East Brook Mall and Windham Recreation Park are located nearby.
8/10 Very Good! (1,012 reviews)
"Everything was perfect. We are looking forward to our next stay."

Reviewed on Oct 22, 2026

Opens in a new windowInn on Storrs
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Book a stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions PeoplesBank Arena and Bushnell Park are located nearby.
Opens in a new windowThe Capitol Hotel
Hyatt Place Uncasville - Casino Area

Hyatt Place Uncasville - Casino Area

3 out of 5
2049 Norwich Montville CT
Book a stay at this business-friendly hotel in Montville. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mohegan Sun Casino and Mohegan Sun Arena are located nearby.
Opens in a new windowHyatt Place Uncasville - Casino Area
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Publick House Historic Inn and Country Motor Lodge

Publick House Historic Inn and Country Motor Lodge

2.5 out of 5
277 Main Street (RT 131) Sturbridge MA
Book a stay at this spa resort in Sturbridge. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Town Common and Sturbridge Common Historic District are located nearby.
9.2/10 Wonderful! (1,790 reviews)
"We love the Publick House; we've stayed there approximately two dozen times on our way to/from Maine. While this was still a good visit, we asked to change rooms because the toilet ran continuously, and the bathroom fan was so loud that it could be heard outside our room door. We were able to change ..."

Reviewed on Oct 21, 2026

Opens in a new windowPublick House Historic Inn and Country Motor Lodge
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 Tolland County?
Within the last seven days, the cheapest roundtrip flight to Tolland County cost $63 on our site. Search through our incredible deals, make your booking and prepare for your next exciting getaway. This price was available on Travelocity for flights to Tolland County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Tolland County?
According to Travelocity's direct return flight demand between January and December last year, November is the cheapest time to board a plane to Tolland County. Keep an eye out for flights throughout this month and snag an incredible deal today.
How can I check my flight status to Tolland County?
Whether you want to view the status of your flight to Tolland County or amend your journey, you'll find everything you need on our customer portal, Trips. Click on "Trips" at the top of our homepage, then log in or open a new account. Another handy way to manage all your bookings is with the Travelocity app. Get real-time flight status alerts and easily share updates with any family flying with you.
How do I find the best deals on flights to Tolland County?
Being flexible with your dates is one way to nab an amazing deal. Travelocity makes it a snap to find your perfect fare through the "Flexible dates" function. First, search for your Tolland County flight, then compare the cheapest prices for surrounding dates by hitting the "Flexible dates" box above. Booking early and avoiding peak travel periods are other suggestions. In the last seven days, the lowest price for a return flight to Tolland County was $63 on our site. 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 Tolland County with Travelocity?
Where to start! With our cheap flights to Tolland County, rental cars and activities, you'll discover all you need for a great getaway with Travelocity. Reserve your cheap family flights and make use of our 24/7 social media support and free cancellations on select hotels if you need. Our goal is to provide hassle-free travel whenever you book with us so that you can spend less time worrying and more time making memories with your travel crew.
What are the most popular flight routes to Tolland County?
As a favorite tourist destination, it's a cinch to find flights to Tolland County. Here are some of the major routes:

  • 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 Tolland County on average?
Plane tickets for roundtrip flights to Tolland County were priced between $63 and $1,817 in the last seven days. As soon as you spot a terrific deal, snap it up and prepare to jet off on your dream vacation with Travelocity. 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 Tolland County?
The length of your direct flight to Tolland County largely depends on your point of origin. For a good idea of what to expect, here are the average flight times for a number of top routes to Tolland County:

  • 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 Tolland County?
This depends mainly on your airline and the duration of your flight. Most airlines generally offer hot meals, snacks and entertainment on long-haul journeys. Whether you're chasing business class flights to Tolland County or cheap flights for family vacations, you'll be looked after from the moment your plane takes off to touchdown.