Cheap Flights to Fairfield County from $44 (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, Oct 10 - Sat, Oct 17
MCO
Orlando Intl.
LGA
LaGuardia
$87 Roundtrip, found 15 hours ago
$87
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Orlando Intl. to LaGuardia, returning Sat, Oct 17, priced at $87 found 15 hours ago
Wed, Sep 30 - Wed, Oct 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$96 Roundtrip, found 2 days ago
$96
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Wed, Sep 30 from Orlando Intl. to Tweed - New Haven Regional, returning Wed, Oct 7, priced at $96 found 2 days ago
Sat, Sep 5 - Tue, Sep 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 8, priced at $102 found 2 days ago
Tue, Aug 25 - Fri, Aug 28
MCO
Orlando Intl.
HPN
Westchester County
$113 Roundtrip, found 11 hours ago
$113
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Tue, Aug 25 from Orlando Intl. to Westchester County, returning Fri, Aug 28, priced at $113 found 11 hours ago
Thu, Sep 10 - Sun, Sep 13
ORD
O'Hare Intl.
HVN
Tweed - New Haven Regional
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Avelo Airlines flight, departing Thu, Sep 10 from O'Hare Intl. to Tweed - New Haven Regional, returning Sun, Sep 13, priced at $118 just found
Thu, Sep 24 - Mon, Sep 28
MCO
Orlando Intl.
ISP
MacArthur
$118 Roundtrip, found 4 hours ago
$118
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Thu, Sep 24 from Orlando Intl. to MacArthur, returning Mon, Sep 28, priced at $118 found 4 hours ago
Wed, Aug 26 - Wed, Aug 26
ORD
O'Hare Intl.
JFK
John F. Kennedy Intl.
$130 Roundtrip, found 2 hours ago
$130
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Wed, Aug 26 from O'Hare Intl. to John F. Kennedy Intl., returning Wed, Aug 26, priced at $130 found 2 hours ago
Sat, Oct 10 - Sat, Oct 17
ORD
O'Hare Intl.
LGA
LaGuardia
$135 Roundtrip, found 4 hours ago
$135
Roundtrip
found 4 hours ago
Select United flight, departing Sat, Oct 10 from O'Hare Intl. to LaGuardia, returning Sat, Oct 17, priced at $135 found 4 hours ago

Best Fairfield County Flight and Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Radio Hotel
4.0-star property

Radio Hotel

Sep 10 - Sep 14

4 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,174, price is now $587 per person
$587
per person
found 1 day ago
Hotel St. James
3.0-star property

Hotel St. James

Aug 13 - Aug 20

7 night stay

Atlanta (ATL) to New York (JFK)

Frontier Airlines • Roundtrip • Coach
Price was $1,450, price is now $720 per person
$720
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Aug 13 - Aug 20

7 night stay

Atlanta (ATL) to Newark Liberty Intl. Airport (EWR)

Frontier Airlines • Roundtrip • Coach
Price was $1,992, price is now $1,014 per person
$1,014
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 Greenwich Avenue and E. Gaynor Brennan Golf Course are located nearby.
8.6/10 Excellent! (1,066 reviews)
"We visited the hotel for the weekend for a wedding. Everything was delightful. The room was spacious and comfortable."

Reviewed on Jul 7, 2026

Opens in a new windowHyatt Regency Greenwich
La Quinta Inn & Suites by Wyndham Stamford / New York City

La Quinta Inn & Suites by Wyndham Stamford / New York City

3 out of 5
135 Harvard Avenue Stamford CT
Stay at this hotel in Stamford. Enjoy free breakfast, free WiFi, and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Greenwich Avenue and E. Gaynor Brennan Golf Course are located nearby.
6.6/10 (1,522 reviews)
"Front staff was great. The room was mostly clean, and needed repairs. The door took extra effort to close, the patio door didn't lock and there was dog poop on it. The water sometimes had yellowish color to it. The alarm clock went off at 6am and it took me a while to figure out how to turn it off. ..."

Reviewed on Jul 8, 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Stamford / New York City
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! (1,290 reviews)
"The room appeared clean, but in the morning, we woke up to cockroaches on the bed pillow. I had my 10-month-old with me, and several roaches were crawling next to where he was lying on the bed. I quickly jumped up and packed up. Left breakfast that my fiance had just bought for us and RAN as fast ..."

Reviewed on Jul 7, 2026

Opens in a new windowEthan Allen Hotel
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EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7 Norwalk CT
Book a stay at this business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Gateway Shopping Center and Silvermine Arts Center are located nearby.
Opens in a new windowEVEN Hotel Norwalk by IHG
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 $87. 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 15 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 October. 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 $87. 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 $87 and $135 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.