Flights To Litchfield County - Cheap Flights Starting at CA $377

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A calm river reflecting trees and houses, a bridge, and a park with benches.

New Milford

Flights
New Milford
A lake surrounded by trees with autumn foliage, picnic tables, and a clear sky.

Torrington

Flights
Torrington

How Much Does it Cost To Fly To Litchfield County?

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

Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 1 day ago
CA $672
Roundtrip
found 1 day ago
Select United flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 1 day ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 1 day ago
CA $672
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 1 day ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $672 Roundtrip, found 1 day ago
CA $672
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $672 found 1 day ago
Mon, Nov 9 - Sat, Nov 14
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $688 Roundtrip, found 1 day ago
CA $688
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Nov 9 from Pearson Intl. to Bradley Intl., returning Sat, Nov 14, priced at CA $688 found 1 day ago
Fri, Nov 20 - Sat, Nov 21
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $704 Roundtrip, found 9 hours ago
CA $704
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Fri, Nov 20 from Pearson Intl. to Bradley Intl., returning Sat, Nov 21, priced at CA $704 found 9 hours ago
Thu, Nov 5 - Sun, Nov 8
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $705 Roundtrip, found 1 day ago
CA $705
Roundtrip
found 1 day ago
Select American Airlines flight, departing Thu, Nov 5 from Pearson Intl. to Bradley Intl., returning Sun, Nov 8, priced at CA $705 found 1 day ago
Wed, Oct 28 - Thu, Nov 5
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $721 Roundtrip, found 3 days ago
CA $721
Roundtrip
found 3 days ago
Select United flight, departing Wed, Oct 28 from Pearson Intl. to Bradley Intl., returning Thu, Nov 5, priced at CA $721 found 3 days ago
Tue, Oct 20 - Tue, Oct 27
YYZ
Pearson Intl.
BDL
Bradley Intl.
CA $722 Roundtrip, found 1 day ago
CA $722
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Oct 20 from Pearson Intl. to Bradley Intl., returning Tue, Oct 27, priced at CA $722 found 1 day ago
OriginDestinationTravel datesFlights from*
MCOEast HavenOctober 30 to November 2CA $259
FLLEast HavenNovember 13 to November 15CA $266
FLLWindsor LocksNovember 13 to November 17CA $278
SJUWindsor LocksOctober 23 to October 26CA $282
MCOWindsor LocksNovember 3 to November 4CA $289
SJUEast HavenNovember 20 to November 28CA $307
LAXWindsor LocksOctober 24 to October 30CA $504
AVTWindsor LocksNovember 6 to November 9CA $762
SFOWindsor LocksNovember 29 to December 3CA $1,659
*Prices include taxes and fees
OriginDestinationTravel datesFlights from*
FLLEast HavenOctober 10 to October 14CA $448
MCOWindsor LocksOctober 10 to October 18CA $502
SJUWindsor LocksOctober 9 to October 19CA $512
MCOEast HavenOctober 10 to October 18CA $732
FLLWindsor LocksOctober 10 to October 14CA $744
LAXWindsor LocksOctober 10 to October 12CA $921
*Prices include taxes and fees
Price found within the past 48 hours. Click for updated prices.
Lotte New York Palace
4.5-star property

Lotte New York Palace

Dec 27 - Dec 30

3 night stay

Hamilton (YHM) to New York (JFK)

Air Canada • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $2,969, price is now CA $1,829 per person
CA $1,829
per person
found 6 hours ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Nov 14 - Nov 17

3 night stay

Montreal (YUL) to New Haven (HVN)

Porter Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was CA $3,263, price is now CA $1,837 per person
CA $1,837
per person
found 24 hours ago
1 Hotel Central Park
5.0-star property

1 Hotel Central Park

Oct 11 - Oct 16

5 night stay

Toronto (YTO) to New York (JFK)

American Airlines • Coach

New York (JFK) to Toronto (YTO)

Delta • Coach
Save 100% on your flight
Price was CA $6,213, price is now CA $3,776 per person
CA $3,776
per person
found 1 day ago
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Travelers ❤️ These Litchfield County 🏨

Rocky River Inn

Rocky River Inn

3 out of 5
236 Kent Road New Milford CT
Stay at this hotel in New Milford. Enjoy free WiFi, free parking, and cable/satellite TV service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Emmanuel Williamson Park and Town Meadows are located nearby.
8.6/10 Excellent! (925 reviews)
"Linda Pleasantly surprised with our accommodations. Large room and bathroom was clean. Linens and towels provided daily. Parking outside the room. Location is convenient to amazing restaurants and gas stations. Would definitely recommend this inn."

Reviewed on Oct 7, 2026

Opens in a new windowRocky River Inn
Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5 out of 5
118 Woodbury Rd. Washington CT
Book a stay at this luxury hotel in Washington. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Steep Rock Preserve and Institute for American Indian Studies Museum and Research Center are located nearby.
9.4/10 Exceptional! (65 reviews)
"Everything was perfect—the room, the service, the restaurant, the spa; everything was perfect. An unforgettable experience."

Reviewed on Sep 13, 2026

Opens in a new windowMayflower Inn & Spa, Auberge Collection
Days Inn by Wyndham Torrington

Days Inn by Wyndham Torrington

2 out of 5
492 East Main St Torrington CT
Book a stay at this business-friendly motel in Torrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hotchkiss-Fyler House Museum and Warner Theater are located nearby.
Opens in a new windowDays Inn by Wyndham Torrington
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Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 out of 5
74 Interlaken Road Lakeville CT
Book a stay at this spa hotel in Lakeville. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Holley-Williams House Museum and Gay Woods Hill are located nearby.
8.2/10 Very good! (315 reviews)
"Needs a renovation and new furniture. Bed was comfortable though."

Reviewed on Oct 6, 2026

Opens in a new windowInterlaken Inn & Resort
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 Litchfield County?
The next vacation you take doesn't have to blow a hole in your budget. Within the last seven days, the cheapest roundtrip flight to Litchfield County cost CA $259. Find a cheap fare and spend the money you save on unforgettable experiences. This price was available on Travelocity for flights to Litchfield County departing within the next year. Prices and availability are subject to change. Additional terms apply.
What is the cheapest month to fly to Litchfield County?
Make sure you leave October clear in your calendar, because it's the most affordable month to fly to Litchfield County. That's according to Travelocity's direct flight demand between January and December last year. With more money in your pocket, you can splurge on a hotel upgrade, go to a concert or whatever floats your boat!
How can I check my flight status to Litchfield County?
Head to our helpful portal, Trips. You'll find just about everything related to your flight to Litchfield County here, including valuable information about any gate changes, flight delays and more. Trips is found at the top of the Travelocity homepage. Just sign up, log in and get the answers to your questions. Or you can access your itinerary on the move and get real-time itinerary updates with the Travelocity app. All your itineraries are in one place, so you can share details with any members of your family flying with you.
How do I find the best deals on flights to Litchfield County?
It's always good to book early, and if you can, avoid traveling during peak periods. Another great way to save is by hitting the "Flexible dates" box at the top of the page after searching for your flights. You'll then see prices for nearby days. In the last seven days, the best price for a return flight to Litchfield County was CA $259. 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 Litchfield County with Travelocity?
Search for cheap flights to Litchfield County with Travelocity and begin arranging your next big adventure. With 24/7 customer assistance during every step of your trip and a Price Match Guarantee, we take the stress out of reserving cheap family flights, hotels, rental cars and more. Lock in a fantastic deal today and brace yourself for an unforgettable adventure.
What are the most popular flight routes to Litchfield County?
Whether you're looking for a brief trip or a long escape, we can help you lock in your ideal flight to Litchfield County. The top flight routes to this destination include:

  • 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 Litchfield County on average?
Passengers were picking up roundtrip flights to Litchfield County for between CA $259 and CA $1,659 with Travelocity in the last seven days. Whether you're looking to fly budget or first class, we'll help you find a wonderful deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.