Cheap Flights to Fairfield County from $20 (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.

Sat, Nov 14 - Wed, Nov 18
MCO
Orlando Intl.
SWF
Stewart Intl.
$35 Roundtrip, found 4 days ago
$35
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Nov 14 from Orlando Intl. to Stewart Intl., returning Wed, Nov 18, priced at $35 found 4 days ago
Wed, Nov 11 - Wed, Nov 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$40 Roundtrip, found 4 days ago
$40
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Stewart Intl., returning Wed, Nov 11, priced at $40 found 4 days ago
Wed, Nov 11 - Wed, Nov 11
MCO
Orlando Intl.
SWF
Stewart Intl.
$83 Roundtrip, found 4 days ago
$83
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Wed, Nov 11 from Orlando Intl. to Stewart Intl., returning Wed, Nov 11, priced at $83 found 4 days ago
Tue, Jan 5 - Thu, Jan 7
ATL
Hartsfield-Jackson Atlanta Intl.
LGA
LaGuardia
$98 Roundtrip, found 6 hours ago
$98
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Jan 5 from Hartsfield-Jackson Atlanta Intl. to LaGuardia, returning Thu, Jan 7, priced at $98 found 6 hours ago
Wed, Jan 27 - Sat, Jan 30
MCO
Orlando Intl.
LGA
LaGuardia
$110 Roundtrip, found 6 hours ago
$110
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Wed, Jan 27 from Orlando Intl. to LaGuardia, returning Sat, Jan 30, priced at $110 found 6 hours ago
Thu, Feb 4 - Sun, Feb 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$111 Roundtrip, found 6 days ago
$111
Roundtrip
found 6 days ago
Select Breeze Airways flight, departing Thu, Feb 4 from Orlando Intl. to Tweed - New Haven Regional, returning Sun, Feb 7, priced at $111 found 6 days ago
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, found 9 hours ago
$128
Roundtrip
found 9 hours ago
Select Avelo Airlines flight, departing Sat, Dec 5 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Dec 12, priced at $128 found 9 hours ago
Tue, Dec 8 - Tue, Dec 8
MCO
Orlando Intl.
HPN
Westchester County
$142 Roundtrip, found 5 days ago
$142
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Tue, Dec 8 from Orlando Intl. to Westchester County, returning Tue, Dec 8, priced at $142 found 5 days ago
Fri, Nov 13 - Mon, Nov 16
MCO
Orlando Intl.
JFK
John F. Kennedy Intl.
$159 Roundtrip, just found
$159
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, Nov 13 from Orlando Intl. to John F. Kennedy Intl., returning Mon, Nov 16, priced at $159 just found

Best Fairfield County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Dolce by Wyndham Parsippany
4.0-star property

Dolce by Wyndham Parsippany

Dec 31 - Jan 5

5 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $630, price is now $329 per person
$329
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Dec 8 - Dec 11

3 night stay

Dallas (DFW) to New Haven (HVN)

Southwest Airlines • Coach

New Haven (HVN) to Dallas (DFW)

Frontier Airlines • Coach
Price was $2,280, price is now $1,097 per person
$1,097
per person
found 14 hours ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Dec 4 - Dec 9

5 night stay

Atlanta (ATL) to New York (JFK)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $3,729, price is now $2,063 per person
$2,063
per person
found 1 day ago
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Travelers ❤️ These Fairfield County 🏨

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 Capitol Theatre and E. Gaynor Brennan Golf Course are located nearby.
8.8/10 Excellent! (1,196 reviews)
"The room was cold. An engineer tried to improve the heat, but couldn't, and said the we could turn off the heat and the room would warm up. We turned it off and the room didn't warm up."

Reviewed on Oct 24, 2026

Opens in a new windowHyatt Regency Greenwich
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 Capitol Theatre and Bush Holley House Museum are located nearby.
Opens in a new windowJ House Greenwich
The Armon Stamford Hotel & Conference

The Armon Stamford Hotel & Conference

2.5 out of 5
2701 Summer St Stamford CT
Book a stay at this business-friendly hotel in Stamford. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Hand & Stone Massage and Facial Spa and E. Gaynor Brennan Golf Course are located nearby.
Opens in a new windowThe Armon Stamford Hotel & Conference
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The Stamford Hotel

The Stamford Hotel

3.5 out of 5
700 East Main Street Stamford CT
Book a stay at this business-friendly hotel in Stamford. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Stamford Town Center and Stamford Public Library - Ferguson Library are located nearby.
Opens in a new windowThe Stamford Hotel
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 $35. 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 16 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 November. 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 $35. 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 $35 and $159 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.