Cheap Flights to Litchfield County from $50 (2026/2027)

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Litchfield

Flights
Litchfield

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.

Thu, Dec 10 - Sun, Dec 13
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Dec 13, priced at $100 found 2 days ago
Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$111 Roundtrip, found 3 days ago
$111
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Jan 28 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Jan 31, priced at $111 found 3 days ago
Sat, Oct 3 - Tue, Oct 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$114 Roundtrip, found 6 days ago
$114
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Sat, Oct 3 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Oct 6, priced at $114 found 6 days ago
Wed, Sep 2 - Wed, Sep 9
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$115 Roundtrip, found 3 days ago
$115
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Sep 2 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 9, priced at $115 found 3 days ago
Thu, Dec 10 - Mon, Dec 14
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, found 4 days ago
$118
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Dec 10 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Dec 14, priced at $118 found 4 days ago
Wed, Sep 2 - Wed, Sep 9
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$120 Roundtrip, found 3 days ago
$120
Roundtrip
found 3 days ago
Select Avelo Airlines flight, departing Wed, Sep 2 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Sep 9, priced at $120 found 3 days ago
Mon, Sep 21 - Mon, Sep 28
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$133 Roundtrip, found 5 hours ago
$133
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Mon, Sep 21 from Fort Lauderdale - Hollywood Intl. to Tweed - New Haven Regional, returning Mon, Sep 28, priced at $133 found 5 hours ago
Thu, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 2 hours ago
$142
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Bradley Intl., returning Mon, Sep 14, priced at $142 found 2 hours ago
OriginDestinationTravel DatesFlights From*
MCOEast HavenOctober 3 to October 6$114
FLLEast HavenSeptember 21 to September 28$133
MCOWindsor LocksSeptember 10 to September 14$142
SJUWindsor LocksSeptember 16 to September 23$158
FLLWindsor LocksSeptember 17 to September 23$160
SJUEast HavenSeptember 12 to September 16$199
MIAWindsor LocksOctober 16 to October 19$201
LAXWindsor LocksOctober 31 to November 7$272
SFOWindsor LocksSeptember 28 to October 3$337
STIWindsor LocksNovember 5 to November 16$465
SDQWindsor LocksSeptember 15 to October 13$484
FCOWindsor LocksNovember 9 to November 15$918
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOEast HavenAugust 30 to September 2$191
FLLEast HavenAugust 29 to September 5$207
MCOWindsor LocksAugust 29 to September 2$246
FLLWindsor LocksAugust 29 to August 31$300
SJUWindsor LocksAugust 29 to September 19$326
MIAWindsor LocksAugust 29 to August 31$419
SJUEast HavenAugust 28 to August 31$442
LAXWindsor LocksAugust 28 to August 31$471
SFOWindsor LocksAugust 28 to August 30$674
STIWindsor LocksAugust 30 to September 6$944
SDQWindsor LocksAugust 28 to September 1$1,091
*Prices include taxes and fees

Best Litchfield County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Nov 6 - Nov 8

2 night stay

Atlanta (ATL) to New Haven (HVN)

Xtra Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,510, price is now $800 per person
$800
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Sep 24 - Sep 27

3 night stay

Atlanta (ATL) to New York (JFK)

JetBlue Airways • Coach

New York (JFK) to Atlanta (ATL)

American Airlines • Coach
Price was $3,494, price is now $1,672 per person
$1,672
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Nov 5 - Nov 9

4 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,447, price is now $812 per person
$812
per person
found 1 day ago
Don't see what you're looking for?
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Travelers ❤️ These Litchfield County 🏨

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! (63 reviews)
"Beautiful property with lovely pool and spa area. The rooms are beautifully decorated. The staff are all friendly, welcoming, and very helpful. The grounds and gardens are well maintained. The hiking trail is highly recommended. My room in the main house was a bit noisy; the room above mine appeared ..."

Reviewed on Aug 21, 2026

Opens in a new windowMayflower Inn & Spa, Auberge Collection
Americas Best Value Inn Torrington CT

Americas Best Value Inn Torrington CT

2.5 out of 5
395 Winsted Rd Torrington CT
Book a stay at this business-friendly hotel in Torrington. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Sunnybrook State Park and Hotchkiss-Fyler House Museum are located nearby.
5.6/10 (811 reviews)
"Obviously not vacuumed between stays"

Reviewed on Aug 23, 2026

Opens in a new windowAmericas Best Value Inn Torrington CT
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.
7.4/10 Good! (1,006 reviews)
"Killed a huge spider in the room. Low water pressure. Bathroom tub was clogged"

Reviewed on Aug 23, 2026

Opens in a new windowDays Inn by Wyndham Torrington
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The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road Litchfield CT
Book a stay at this spa hotel in Litchfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions White Memorial Conservation Center and Mount Tom State Park are located nearby.
9.2/10 Wonderful! (1,002 reviews)
"From the first time stepping on the property we felt welcome. The staff was accommodating and invited us to enjoy the amenities while we waited for our room (we were early for check in). We took advantage and walked the property before heading off to explore the area. When we returned, we checked ..."

Reviewed on Aug 21, 2026

Opens in a new windowThe Litchfield Inn
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 $100. 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 December 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 $100. 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 $100 and $1,091 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.
How long is the average flight to Litchfield County?
Listed below are a number of preferred direct flights to Litchfield County alongside their average flight duration:

  • 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 Litchfield County?
The flight time and whether you choose a low-priced or full-service carrier will determine what to expect on board. If you're seeking long-haul flights to Litchfield County, entertainment, drinks and food should come as standard. Trying to find cheap flights for family vacations? Check out the deals from budget carriers. Usually, these airlines don't offer as many inclusions, or you'll need to pay an extra fee for them.