Flights To Fairfield County - Cheap Flights Starting at CA $87

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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, Sep 10 - Mon, Sep 14
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $189 Roundtrip, found 4 days ago
CA $189
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Sep 14, priced at CA $189 found 4 days ago
Thu, Sep 10 - Wed, Sep 23
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $209 Roundtrip, found 3 days ago
CA $209
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Thu, Sep 10 from Orlando Intl. to Stewart Intl., returning Wed, Sep 23, priced at CA $209 found 3 days ago
Mon, Sep 14 - Wed, Sep 23
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $210 Roundtrip, found 3 days ago
CA $210
Roundtrip
found 3 days ago
Select Breeze Airways flight, departing Mon, Sep 14 from Orlando Intl. to Stewart Intl., returning Wed, Sep 23, priced at CA $210 found 3 days ago
Sat, Sep 5 - Tue, Sep 8
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $229 Roundtrip, found 1 day ago
CA $229
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Sat, Sep 5 from Orlando Intl. to Tweed - New Haven Regional, returning Tue, Sep 8, priced at CA $229 found 1 day ago
Fri, Oct 2 - Mon, Oct 5
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
CA $233 Roundtrip, found 21 hours ago
CA $233
Roundtrip
found 21 hours ago
Select Breeze Airways flight, departing Fri, Oct 2 from Orlando Intl. to Tweed - New Haven Regional, returning Mon, Oct 5, priced at CA $233 found 21 hours ago
Wed, Sep 30 - Sun, Oct 4
MCO
Orlando Intl.
SWF
Stewart Intl.
CA $234 Roundtrip, found 2 days ago
CA $234
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Sep 30 from Orlando Intl. to Stewart Intl., returning Sun, Oct 4, priced at CA $234 found 2 days ago
Thu, Nov 12 - Sun, Nov 15
MCO
Orlando Intl.
LGA
LaGuardia
CA $287 Roundtrip, found 1 hour ago
CA $287
Roundtrip
found 1 hour ago
Select JetBlue Airways flight, departing Thu, Nov 12 from Orlando Intl. to LaGuardia, returning Sun, Nov 15, priced at CA $287 found 1 hour ago
Thu, Nov 12 - Mon, Nov 16
MCO
Orlando Intl.
LGA
LaGuardia
CA $289 Roundtrip, found 5 days ago
CA $289
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Nov 12 from Orlando Intl. to LaGuardia, returning Mon, Nov 16, priced at CA $289 found 5 days ago
Thu, Sep 10 - Sun, Sep 13
YUL
Pierre Elliott Trudeau Intl.
LGA
LaGuardia
CA $400 Roundtrip, found 1 day ago
CA $400
Roundtrip
found 1 day ago
Select Air Canada flight, departing Thu, Sep 10 from Pierre Elliott Trudeau Intl. to LaGuardia, returning Sun, Sep 13, priced at CA $400 found 1 day ago
Sun, Sep 6 - Sun, Sep 27
YYZ
Pearson Intl.
LGA
LaGuardia
CA $411 Roundtrip, found 2 days ago
CA $411
Roundtrip
found 2 days ago
Select Porter Airlines flight, departing Sun, Sep 6 from Pearson Intl. to LaGuardia, returning Sun, Sep 27, priced at CA $411 found 2 days ago
Wed, Sep 9 - Tue, Sep 15
YYZ
Pearson Intl.
JFK
John F. Kennedy Intl.
CA $412 Roundtrip, found 1 day ago
CA $412
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 9 from Pearson Intl. to John F. Kennedy Intl., returning Tue, Sep 15, priced at CA $412 found 1 day ago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Manhattan Times Square
4.0-star property

Hotel Riu Plaza Manhattan Times Square

Oct 2 - Oct 5

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $2,161, price is now CA $1,300 per person
CA $1,300
per person
found 1 day ago
Beechmont - Perfect for Family Retreat!
5.0-star property

Beechmont - Perfect for Family Retreat!

Oct 15 - Oct 19

4 night stay

Toronto (YYZ) to New Haven (HVN)

Air Canada • Roundtrip • Coach
Price was CA $4,142, price is now CA $1,855 per person
CA $1,855
per person
found 1 hour ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Oct 2 - Oct 5

3 night stay

Buffalo (BUF) to New York (JFK)

JetBlue Airways • Roundtrip • Coach
Price was CA $3,566, price is now CA $1,780 per person
CA $1,780
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 E. Gaynor Brennan Golf Course and Mianus Park are located nearby.
8.8/10 Excellent! (1,113 reviews)
"The TV didn't work in our room"

Reviewed on Aug 21, 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 Hartford HealthCare Amphitheater and Roosevelt Forest are located nearby.
Opens in a new windowTrumbull Marriott Shelton
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 Center Seven Shopping Center and Gateway Shopping Center are located nearby.
Opens in a new windowEVEN Hotel Norwalk by IHG
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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! (1,416 reviews)
"We’ve stayed in many Connecticut hotels, and this is the cleanest of them all. Ethan Allen clearly takes pride in their brand, and this hotel proves it."

Reviewed on Aug 20, 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 CA $189. 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 September. 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 $189. 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 $189 and CA $412 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.