Flights To Fairfield County - Cheap Flights Starting at CA $74

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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.

Sun, Jan 17 - Thu, Jan 21
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $145 Roundtrip, just found
CA $145
Roundtrip
just found
Select Breeze Airways flight, departing Sun, Jan 17 from Raleigh - Durham Intl. to Westchester County, returning Thu, Jan 21, priced at CA $145 just found
Thu, Dec 3 - Mon, Dec 7
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $147 Roundtrip, found 1 day ago
CA $147
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Thu, Dec 3 from Raleigh - Durham Intl. to Westchester County, returning Mon, Dec 7, priced at CA $147 found 1 day ago
Wed, Dec 9 - Wed, Dec 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $152 Roundtrip, found 1 day ago
CA $152
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Wed, Dec 9 from Raleigh - Durham Intl. to Westchester County, returning Wed, Dec 16, priced at CA $152 found 1 day ago
Sat, Oct 31 - Sat, Nov 7
RDU
Raleigh - Durham Intl.
SWF
Stewart Intl.
CA $187 Roundtrip, found 1 day ago
CA $187
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Sat, Oct 31 from Raleigh - Durham Intl. to Stewart Intl., returning Sat, Nov 7, priced at CA $187 found 1 day ago
Fri, Nov 6 - Mon, Nov 9
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $190 Roundtrip, found 4 days ago
CA $190
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Nov 6 from Raleigh - Durham Intl. to Westchester County, returning Mon, Nov 9, priced at CA $190 found 4 days ago
Mon, Nov 2 - Mon, Nov 16
RDU
Raleigh - Durham Intl.
ISP
MacArthur
CA $217 Roundtrip, found 1 day ago
CA $217
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Nov 2 from Raleigh - Durham Intl. to MacArthur, returning Mon, Nov 16, priced at CA $217 found 1 day ago
Thu, Oct 22 - Mon, Oct 26
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
CA $286 Roundtrip, found 7 hours ago
CA $286
Roundtrip
found 7 hours ago
Select Avelo Airlines flight, departing Thu, Oct 22 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Oct 26, priced at CA $286 found 7 hours ago
Thu, Oct 29 - Sun, Nov 1
YYZ
Pearson Intl.
LGA
LaGuardia
CA $378 Roundtrip, just found
CA $378
Roundtrip
just found
Select Porter Airlines flight, departing Thu, Oct 29 from Pearson Intl. to LaGuardia, returning Sun, Nov 1, priced at CA $378 just found
Wed, Oct 28 - Sat, Oct 31
YYZ
Pearson Intl.
JFK
John F. Kennedy Intl.
CA $378 Roundtrip, just found
CA $378
Roundtrip
just found
Select Delta flight, departing Wed, Oct 28 from Pearson Intl. to John F. Kennedy Intl., returning Sat, Oct 31, priced at CA $378 just found
Wed, Dec 2 - Mon, Dec 7
YUL
Pierre Elliott Trudeau Intl.
LGA
LaGuardia
CA $396 Roundtrip, just found
CA $396
Roundtrip
just found
Select Delta flight, departing Wed, Dec 2 from Pierre Elliott Trudeau Intl. to LaGuardia, returning Mon, Dec 7, priced at CA $396 just found
Wed, Dec 9 - Wed, Dec 16
RDU
Raleigh - Durham Intl.
HPN
Westchester County
CA $414 Roundtrip, found 1 day ago
CA $414
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Dec 9 from Raleigh - Durham Intl. to Westchester County, returning Wed, Dec 16, priced at CA $414 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
Night Hotel Broadway
3.0-star property

Night Hotel Broadway

Dec 10 - Dec 13

3 night stay

Ottawa (YOW) to New York (JFK)

Porter Airlines • Roundtrip • Coach
Save 100% on your flight
Price was CA $2,021, price is now CA $1,240 per person
CA $1,240
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Dec 10 - Dec 13

3 night stay

Montreal (YUL) to New Haven (HVN)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was CA $3,296, price is now CA $1,871 per person
CA $1,871
per person
found 8 hours ago
33 Hotel, New York City, Seaport
5.0-star property

33 Hotel, New York City, Seaport

Dec 26 - Dec 31

5 night stay

Ottawa (YOW) to New York (JFK)

United • Roundtrip • Coach
Save 100% on your flight
Price was CA $3,083, price is now CA $1,850 per person
CA $1,850
per person
found 21 hours ago
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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.
8.8/10 Excellent! (1,172 reviews)
"Large and conveniently located. Showing some age. Outlet in the room didnt work, shower curtain needs replacement. Promised a rollaway but then said no and shrugged it off. Breakfast service slow and overpriced"

Reviewed on Oct 4, 2026

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.
9/10 Wonderful! (1,002 reviews)
"Great stay loved the room and the tv in the bathroom mirror was amazing. We ate at Tony’s restaurant while there which was fantastic. My only complaint and area of improvement was the breakfast provided in the AM was awful. Just a few baked pastries,granola bars and yogurt provided. Basically something ..."

Reviewed on Oct 4, 2026

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 CA $145. 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 CA $145. 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 CA $145 and CA $414 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.