Cheap Flights to Fairfield County from $42 (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.

Fri, Jan 22 - Mon, Jan 25
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$83 Roundtrip, found 2 hours ago
$83
Roundtrip
found 2 hours ago
Select Avelo Airlines flight, departing Fri, Jan 22 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Jan 25, priced at $83 found 2 hours ago
Sat, Jan 9 - Wed, Jan 13
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
$102 Roundtrip, found 5 hours ago
$102
Roundtrip
found 5 hours ago
Select Breeze Airways flight, departing Sat, Jan 9 from Raleigh - Durham Intl. to Stewart Intl., returning Wed, Jan 13, priced at $102 found 5 hours ago
Fri, Jan 8 - Mon, Jan 11
RDU
Raleigh - Durham Intl.
ISP
MacArthur
$122 Roundtrip, found 1 hour ago
$122
Roundtrip
found 1 hour ago
Select Breeze Airways flight, departing Fri, Jan 8 from Raleigh - Durham Intl. to MacArthur, returning Mon, Jan 11, priced at $122 found 1 hour ago
Thu, Jan 21 - Wed, Jan 27
MCO
Orlando Intl.
LGA
LaGuardia
$123 Roundtrip, found 1 hour ago
$123
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Jan 21 from Orlando Intl. to LaGuardia, returning Wed, Jan 27, priced at $123 found 1 hour ago
Fri, Jan 8 - Mon, Jan 11
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$124 Roundtrip, just found
$124
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Jan 8 from Tampa Intl. to Tweed - New Haven Regional, returning Mon, Jan 11, priced at $124 just found
Sun, Jan 17 - Sun, Jan 24
PIE
St. Petersburg-Clearwater Intl.
SWF
Stewart Intl.
$124 Roundtrip, just found
$124
Roundtrip
just found
Select Allegiant Air flight, departing Sun, Jan 17 from St. Petersburg-Clearwater Intl. to Stewart Intl., returning Sun, Jan 24, priced at $124 just found
Tue, Jan 12 - Sat, Jan 23
TPA
Tampa Intl.
LGA
LaGuardia
$125 Roundtrip, found 7 hours ago
$125
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Jan 12 from Tampa Intl. to LaGuardia, returning Sat, Jan 23, priced at $125 found 7 hours ago
Wed, Dec 2 - Sat, Dec 5
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$128 Roundtrip, just found
$128
Roundtrip
just found
Select Avelo Airlines flight, departing Wed, Dec 2 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Dec 5, priced at $128 just found
Tue, Jan 12 - Tue, Jan 19
MCO
Orlando Intl.
HPN
Westchester County
$140 Roundtrip, found 15 hours ago
$140
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Tue, Jan 12 from Orlando Intl. to Westchester County, returning Tue, Jan 19, priced at $140 found 15 hours ago
Sat, Dec 5 - Sat, Dec 12
TPA
Tampa Intl.
SWF
Stewart Intl.
$144 Roundtrip, found 3 days ago
$144
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Sat, Dec 5 from Tampa Intl. to Stewart Intl., returning Sat, Dec 12, priced at $144 found 3 days ago
Fri, Jan 29 - Mon, Feb 1
MCO
Orlando Intl.
SWF
Stewart Intl.
$151 Roundtrip, found 10 hours ago
$151
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Fri, Jan 29 from Orlando Intl. to Stewart Intl., returning Mon, Feb 1, priced at $151 found 10 hours ago

Best Fairfield County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Jan 22 - Jan 24

2 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $1,082, price is now $635 per person
$635
per person
found 1 day ago
The St. Regis New York
5.0-star property

The St. Regis New York

Jan 22 - Jan 24

2 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $1,617, price is now $822 per person
$822
per person
found 1 day ago
JW Marriott Essex House New York
4.5-star property

JW Marriott Essex House New York

Jan 6 - Jan 9

3 night stay

Atlanta (ATL) to New York (JFK)

American Airlines • Coach

New York (JFK) to Atlanta (ATL)

Frontier Airlines • Coach
Price was $1,309, price is now $751 per person
$751
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! (1,218 reviews)
"If you want to be woken up on a Sunday at 6:00am with music, this is your place. If you want to sleep in, maybe go somewhere else"

Reviewed on Nov 9, 2026

Opens in a new windowHyatt Regency 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.
7.8/10 Good! (1,013 reviews)
"Very nice hotel! It was pretty much empty when I visited but the room was great and the inside of the hotel was cool and had a lot to offer."

Reviewed on Nov 10, 2026

Opens in a new windowThe Armon Stamford Hotel & Conference
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.
8/10 Very Good! (1,267 reviews)
"The hotel is in a good area close to restaurants and stores. Although this hotel is well worn, the bed was comfortable and it was very quiet at night. I liked the security feature of requiring room key to access the elevator and security guard on Sat night ( which happened to be Halloween). I did ..."

Reviewed on Nov 10, 2026

Opens in a new windowThe Stamford Hotel
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Ethan Allen Hotel

Ethan Allen Hotel

3.5 out of 5
21 Lake Avenue Extension Danbury CT
Book a stay at this business-friendly hotel in Danbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Danbury Fair Mall and Xtreme Play Adventure Park are located nearby.
8/10 Very Good! (1,553 reviews)
"Insane line to check in. There was one person working and we waited 47 minutes to check into our room. How do you only have 1 person working on a Saturday handling check ins. Ridiculous."

Reviewed on Nov 10, 2026

Opens in a new windowEthan Allen 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 $83. 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 $83. 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 $83 and $151 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.