Cheap Flights to Fairfield County from $55 (2026/2027)

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Stamford

Flights
Stamford

How Much Does it Cost To Fly To Fairfield County?

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

Thu, Jan 28 - Sun, Jan 31
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$111 Roundtrip, found 15 hours ago
$111
Roundtrip
found 15 hours 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 15 hours ago
Fri, Nov 13 - Mon, Nov 16
MYR
Myrtle Beach Intl.
SWF
Stewart Intl.
$118 Roundtrip, found 6 hours ago
$118
Roundtrip
found 6 hours ago
Select Allegiant Air flight, departing Fri, Nov 13 from Myrtle Beach Intl. to Stewart Intl., returning Mon, Nov 16, priced at $118 found 6 hours ago
Fri, Jan 22 - Mon, Jan 25
MYR
Myrtle Beach Intl.
ISP
MacArthur
$122 Roundtrip, found 7 hours ago
$122
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Fri, Jan 22 from Myrtle Beach Intl. to MacArthur, returning Mon, Jan 25, priced at $122 found 7 hours ago
Mon, Dec 7 - Mon, Dec 14
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$125 Roundtrip, found 13 hours ago
$125
Roundtrip
found 13 hours ago
Select Avelo Airlines flight, departing Mon, Dec 7 from Myrtle Beach Intl. to Tweed - New Haven Regional, returning Mon, Dec 14, priced at $125 found 13 hours ago
Wed, Jan 6 - Tue, Jan 12
MCO
Orlando Intl.
LGA
LaGuardia
$126 Roundtrip, found 4 hours ago
$126
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Jan 6 from Orlando Intl. to LaGuardia, returning Tue, Jan 12, priced at $126 found 4 hours ago
Sat, Oct 24 - Tue, Oct 27
MCO
Orlando Intl.
ISP
MacArthur
$143 Roundtrip, found 3 days ago
$143
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Oct 24 from Orlando Intl. to MacArthur, returning Tue, Oct 27, priced at $143 found 3 days ago
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando Intl.
SWF
Stewart Intl.
$147 Roundtrip, found 21 hours ago
$147
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Thu, Dec 3 from Orlando Intl. to Stewart Intl., returning Sun, Dec 6, priced at $147 found 21 hours ago
Tue, Nov 3 - Tue, Nov 17
MCO
Orlando Intl.
HPN
Westchester County
$152 Roundtrip, found 6 hours ago
$152
Roundtrip
found 6 hours ago
Select Breeze Airways flight, departing Tue, Nov 3 from Orlando Intl. to Westchester County, returning Tue, Nov 17, priced at $152 found 6 hours ago
Sat, Jan 30 - Tue, Feb 2
SFO
San Francisco Intl.
LGA
LaGuardia
$282 Roundtrip, found 15 hours ago
$282
Roundtrip
found 15 hours ago
Select Southwest Airlines flight, departing Sat, Jan 30 from San Francisco Intl. to LaGuardia, returning Tue, Feb 2, priced at $282 found 15 hours ago
Tue, Dec 1 - Wed, Dec 16
SFO
San Francisco Intl.
HPN
Westchester County
$291 Roundtrip, found 6 hours ago
$291
Roundtrip
found 6 hours ago
Select American Airlines flight, departing Tue, Dec 1 from San Francisco Intl. to Westchester County, returning Wed, Dec 16, priced at $291 found 6 hours ago
Mon, Nov 16 - Wed, Nov 18
SFO
San Francisco Intl.
LGA
LaGuardia
$339 Roundtrip, found 14 hours ago
$339
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Mon, Nov 16 from San Francisco Intl. to LaGuardia, returning Wed, Nov 18, priced at $339 found 14 hours ago

Best Fairfield County Flight and Hotel Packages

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

Dallas (DAL) to New York (JFK)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,228, price is now $1,402 per person
$1,402
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Dec 30 - Jan 3

4 night stay

Orlando (MCO) to New Haven (HVN)

Breeze Airways • Non-stop • Coach

New Haven (HVN) to Orlando (MCO)

Frontier Airlines • Non-stop • Coach
Save 100% on your flight
Price was $3,069, price is now $1,664 per person
$1,664
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Dec 9 - Dec 13

4 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $4,521, price is now $2,631 per person
$2,631
per person
found 8 hours ago
Don't see what you're looking for?
See all available trips from Dallas to Fairfield County
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Travelers ❤️ These Fairfield County 🏨

Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave Stamford CT
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Stamford Town Center and Stamford Public Library - Ferguson Library are located nearby.
Opens in a new windowAmsterdam Hotel
Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue Old Greenwich CT
Book a stay at this business-friendly hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions E. Gaynor Brennan Golf Course and Mianus Park are located nearby.
Opens in a new windowHyatt Regency Greenwich
Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln Trumbull CT
Stay at this hotel in Trumbull. Enjoy an outdoor pool, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Roosevelt Forest and Boothe Memorial Park and Museum are located nearby.
Opens in a new windowTrumbull Marriott Shelton
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J House Greenwich

J House Greenwich

4 out of 5
1114 E. Putnam Ave Riverside CT
Book a stay at this spa hotel in Riverside. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Mianus Park and Bush Holley House Museum are located nearby.
Opens in a new windowJ House Greenwich
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 Fairfield County?
Your next dream vacation doesn't have to make a huge dent in your finances. In the last seven days, the cheapest roundtrip flight to Fairfield County cost $111. Find a cheap seat and spend the money you save on unforgettable experiences. This price was available on Travelocity for flights to Fairfield County departing within the next year. Prices and availability are subject to change. Additional terms apply.
Which airlines fly to Fairfield County?
You'll have your pick of 20 airlines when it's time to organize your flight to Fairfield County. Let Cape Air whisk you to your destination. This highly rated air carrier offers 286 services each month to Bridgeport, Fairfield County's premier city.
What is the cheapest month to fly to Fairfield County?
Spend more money on epic adventures and less on airline tickets by zipping off to Fairfield County in January. This is the best-priced month to jet off to this destination according to Travelocity's direct return flight demand between January and December last year. Browse through our list of flights and get out of town without breaking your budget.
How can I check my flight status to Fairfield County?
"Trips" is your one-stop shop when it comes to details about your flight to Fairfield County. Our convenient customer portal lets you manage everything in the same place, from checking your flight status to making updates to your booking. Click on Trips at the top right of the Travelocity homepage and then create a free account in seconds. Or, download the Travelocity app and access your information while you're on the go. Whether you have the family flying with you or you're a solo wanderer, all your travel plans will be at your fingertips.
How do I find the best deals on flights to Fairfield County?
Be flexible with your dates and there's a good chance you'll find a deal you can't pass up. When searching for flights on Travelocity, click the "Flexible dates" option at the top of the page to see prices for nearby days. Also try to book ahead of schedule and avoid peak periods. In the last seven days, the lowest price for a roundtrip flight to Fairfield County was $111. 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 Fairfield County with Travelocity?
If you're chasing cheap flights to Fairfield County, you'll track down some enticing deals with Travelocity. From cheap family flights with low-cost air carriers to flexible ticket options, we can help with your journey. Experience a worry-free break with our 24/7 customer support, Price Match Guarantee and free cancellations with most hotels. Start planning your travel itinerary and get set to fly away to this fantastic destination.
How much is a flight to Fairfield County on average?
Passengers have picked up roundtrip flights to Fairfield County for between $111 and $339 with Travelocity in the last seven days. Whether you want to fly budget or business class, we'll help you land an awesome deal. These prices were available on Travelocity for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.
What can I expect on a flight to Fairfield County?
How long your flight takes and whether you pick a full-service or low-priced airline play a major role. If you're looking for long-haul flights to Fairfield County, entertainment, drinks and food will be standard inclusions. Trying to find cheap flights for family vacations? Check out the fares with budget carriers. These airlines usually don't have as many inclusions, so be prepared to pay for your drinks and meals.