Cheap flights To Thimble Islands (HVN) from $42

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Cheap Flights to Thimble Islands from $42 One Way, $84 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Jun 4 - Mon, Jun 8
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$84 Roundtrip, found 2 days ago
$84
Roundtrip
found 2 days ago
Select Avelo Airlines flight, departing Thu, Jun 4 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Jun 8, priced at $84 found 2 days ago
Mon, Sep 14 - Mon, Sep 21
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$86 Roundtrip, found 1 day ago
$86
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Mon, Sep 14 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Sep 21, priced at $86 found 1 day ago
Wed, Jun 10 - Thu, Jun 11
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$87 Roundtrip, found 23 hours ago
$87
Roundtrip
found 23 hours ago
Select Avelo Airlines flight, departing Wed, Jun 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Thu, Jun 11, priced at $87 found 23 hours ago
Thu, Nov 19 - Sun, Nov 22
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$88 Roundtrip, found 21 hours ago
$88
Roundtrip
found 21 hours ago
Select Avelo Airlines flight, departing Thu, Nov 19 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Sun, Nov 22, priced at $88 found 21 hours ago
Fri, Jun 5 - Mon, Jun 15
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$91 Roundtrip, found 6 days ago
$91
Roundtrip
found 6 days ago
Select Avelo Airlines flight, departing Fri, Jun 5 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $91 found 6 days ago
Thu, Jun 11 - Mon, Jun 15
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$93 Roundtrip, found 4 days ago
$93
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Thu, Jun 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Jun 15, priced at $93 found 4 days ago
Thu, Jun 11 - Wed, Jun 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$95 Roundtrip, found 1 hour ago
$95
Roundtrip
found 1 hour ago
Select Avelo Airlines flight, departing Thu, Jun 11 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Jun 17, priced at $95 found 1 hour ago
Thu, Jun 4 - Wed, Jun 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$95 Roundtrip, found 4 days ago
$95
Roundtrip
found 4 days ago
Select Avelo Airlines flight, departing Thu, Jun 4 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Jun 17, priced at $95 found 4 days ago
Mon, Jul 20 - Mon, Jul 27
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$98 Roundtrip, found 2 hours ago
$98
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Mon, Jul 20 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Mon, Jul 27, priced at $98 found 2 hours ago
Wed, Jun 10 - Wed, Jun 17
RDU
Raleigh - Durham Intl.
HVN
Tweed - New Haven Regional
$98 Roundtrip, found 1 day ago
$98
Roundtrip
found 1 day ago
Select Avelo Airlines flight, departing Wed, Jun 10 from Raleigh - Durham Intl. to Tweed - New Haven Regional, returning Wed, Jun 17, priced at $98 found 1 day ago

Thimble Islands Flight Information

Traveling To
Thimble Islands
Destination Airport IATA Code
HVN
Number of Airlines Serving
Airlines
Avelo Airlines, Breeze Airways
Flight Price
$84
Earliest Departing Flight
Latest Departing Flight

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Thimble Islands economy flight packages

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

Jul 3 - Jul 10

7 night stay

Dallas (DAL) to New York (JFK)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,203, price is now $1,249 per person
$1,249
per person
found 1 day ago
Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

Jul 3 - Jul 10

7 night stay

Dallas (DAL) to New York (JFK)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,423, price is now $1,361 per person
$1,361
per person
found 1 day ago
1 Hotel Brooklyn Bridge
5.0-star property

1 Hotel Brooklyn Bridge

Jul 1 - Jul 4

3 night stay

Dallas (DFW) to New York (JFK)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,377, price is now $2,027 per person
$2,027
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Dallas to Thimble Islands
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Thimble Islands premium economy flight packages

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

9.2/10 Wonderful! (3,526 reviews)

Jul 3 - Jul 10

7 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,258, price is now $1,304 per person
$1,304
per person
found 1 day ago
Beds are comfortable

Reviewed on May 12, 2026

New York Marriott Marquis
4.5-star property

New York Marriott Marquis

9.4/10 Exceptional! (4,409 reviews)

Jul 2 - Jul 9

7 night stay

Dallas (DFW) to Newark Liberty Intl. Airport (EWR)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $3,054, price is now $1,817 per person
$1,817
per person
found 1 day ago
Our stay was top notch. Everyone was so helpful and we will definitely recommend this as THE place to stay in NYC.

Reviewed on May 24, 2026

Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (3,026 reviews)

Jul 2 - Jul 9

7 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,554, price is now $1,521 per person
$1,521
per person
found 1 day ago
There was unexpected extra fees

Reviewed on May 10, 2026

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Thimble Islands business class flight packages

Price found within the past 48 hours. Click for updated prices.
Dutch Hotel Long Island City New York , Belvilla District 6 Formerly Sonder
3.0-star property

Dutch Hotel Long Island City New York , Belvilla District 6 Formerly Sonder

7.8/10 Good! (330 reviews)

Jun 26 - Jun 28

2 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,124, price is now $947 per person
$947
per person
found 16 hours ago
Very friendly and welcoming staff. Small hotel with nice rooms and 2 beautiful decks with a gorgeous view of nyc skyline.

Reviewed on Jul 22, 2025

The Plaza, A Fairmont Hotel
5.0-star property

The Plaza, A Fairmont Hotel

9/10 Wonderful! (1,003 reviews)

Jun 26 - Jun 28

2 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Save 100% on your flight
Price was $3,052, price is now $2,342 per person
$2,342
per person
found 18 hours ago
My wife and I had a great time at the Plaza. The only thing we noticed that would make a big difference is the bedding (sheets & covers) and mattress should be better quality, softer and much less crinkly. The staff was great, called you by last name and was attentive to our needs/wants.

Reviewed on Jan 13, 2025

Hotel Riu Plaza New York Times Square
4.0-star property

Hotel Riu Plaza New York Times Square

9/10 Wonderful! (3,026 reviews)

Jun 26 - Jun 28

2 night stay

Dallas (DFW) to New York (JFK)

Frontier Airlines • Non-stop roundtrip • BusinessClass
Price was $1,605, price is now $1,267 per person
$1,267
per person
found 18 hours ago
There was unexpected extra fees

Reviewed on May 10, 2026

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See all available trips from Dallas to Thimble Islands
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Thimble Islands first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Iroquois New York
4.5-star property

The Iroquois New York

9.4/10 Exceptional! (1,729 reviews)

Jul 3 - Jul 5

2 night stay

San Juan (SJU) to New York (JFK)

American Airlines • Non-stop • FirstClass

New York (JFK) to San Juan (SJU)

Frontier Airlines • Non-stop • FirstClass
Price was $1,172, price is now $1,048 per person
$1,048
per person
found 16 hours ago
Very convenient location.

Reviewed on Apr 19, 2026

The Chemists’ Club Hotel
4.0-star property

The Chemists’ Club Hotel

9.4/10 Exceptional! (400 reviews)

Jul 3 - Jul 5

2 night stay

San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • FirstClass

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

Frontier Airlines • Non-stop • FirstClass
Price was $1,329, price is now $1,187 per person
$1,187
per person
found 16 hours ago
Hotel was very clean and updated. Staff was exceptional! Check in was seamless and accommodating. The beds were comfortable and quiet. We stayed for 3 nights for a mother/son trip. Close to Grand Central which provided easy access to subway. I would definitely stay again.

Reviewed on Mar 24, 2026

Kixby
4.0-star property

Kixby

9.4/10 Exceptional! (1,888 reviews)

Jul 3 - Jul 5

2 night stay

San Juan (SJU) to Newark Liberty Intl. Airport (EWR)

American Airlines • Non-stop • FirstClass

Newark Liberty Intl. Airport (EWR) to San Juan (SJU)

Frontier Airlines • Non-stop • FirstClass
Price was $1,183, price is now $1,065 per person
$1,065
per person
found 16 hours ago
Lovely hotel. Friendly staff and great location!

Reviewed on Apr 12, 2026

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Thimble Islands

Orbitz is your one stop for guaranteed low prices on Thimble Islands flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

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Our experts will make things even easier by helping you to find the best budget flights to Thimble Islands Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

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Our state of the art mobile apps will allow you to book cheap flights to Thimble Islands from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

Frequently asked questions

What is the best airport to fly to in Thimble Islands?
Find yourself a cheap fare to Tweed - New Haven Regional Airport (HVN). It's the main airport servicing this city and is situated roughly 7 miles west of the downtown area. Once you've touched down, it won't be long before you're experiencing the wonders of Thimble Islands.
How much is a flight to Thimble Islands?
If you're after a round-trip flight, fares ranged between $84 and $98 this past week. The lowest price to travel one-way was $42, departing from Raleigh (RDU).
How to book the cheapest flight to Thimble Islands?
Using Orbitz, you'll uncover some of the most amazing flight deals around from a terrific range of airlines. But if you want to increase your chances of nabbing cheap flights to Thimble Islands, here are a few pointers to get started:

  • Consider departing from or arriving at other airports for a better deal. Enter your preferred departure and arrival points in the form fields, then click on the 'Nearby airports' function below. It will list your options, if any.
  • If you're flexible with your travel schedule, click on the 'Show flexible dates' link. You'll see the flight deals for the days before and after your selected departure. Airfares often vary depending on what day it is.
  • To optimize your results, hit 'Show options.' You can search based on airlines, seating class, nonstop flights and refundable flights. You can also select whether you want to fly in the morning, afternoon or evening under 'Sort & Filter' to the left.
  • The early bird gets the most rewarding savings, so purchase your seats once you've settled on your travel dates. The most affordable airfares get snapped up fast and prices generally increase as the departure date gets closer.
  • Bundle your hotels, flights and car rentals into an impressive package deal. Save your hard-earned money for things you're really excited about, like exploring every corner of Thimble Islands.
  • If you can, avoid flying in peak seasons. Airfares often hit their highest during summer, school breaks and around other vacation times like Easter, Thanksgiving and Christmas.

How long is a flight to Thimble Islands?
You could have time to read a few chapters or more of your novel, or you might get through the whole thing! Flight durations depend on where you're leaving from, but these well-known routes to Thimble Islands will offer some insight:

  • Orlando, FL (MCO-Orlando Intl.) to Tweed - New Haven Regional Airport (HVN) - 2 hours and 40 minutes
  • Fort Lauderdale, FL (FLL-Fort Lauderdale - Hollywood Intl.) to Tweed - New Haven Regional Airport (HVN) - 2 hours and 55 minutes
  • Nashville, TN (BNA-Nashville Intl.) to Tweed - New Haven Regional Airport (HVN) - 2 hours and 10 minutes

What is the best time to book a flight to Thimble Islands?
Catch a bargain and book your tickets to Thimble Islands in January. If you've missed this month, fear not. February and August often have low airfares as well. Make sure you don't snooze on a sale though — cheap flights pop up and vanish in a flash!
What day of the week is the cheapest to book a flight to Thimble Islands?
If you're after inexpensive fares to Thimble Islands, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a fabulous flight deal will be all yours.
What is the cheapest day of the week to fly to Thimble Islands?
According to Orbitz data from 2020, Monday is generally the best day to get cheap flights to Thimble Islands. Tuesday also offers more affordable fares, whereas Saturday has the highest ticket rates. Even though flying out at the weekend may be more convenient, you'll have more money to play with if you take off at the start of the week.
What is the cheapest month to fly to Thimble Islands?
Get set to jet for less in August. This is generally the best month to take off if you want cheap flights to Thimble Islands, according to Orbitz data. The most expensive time to fly is June, so try to avoid this month if you're on a budget.
Which airlines allow free cancellation?
When searching for flights on Orbitz, select "Filter by flexible change policies." This filter will show you all the carriers offering free cancellation within 24 hours of booking and no change fees. Breathe easy knowing that if things unexpectedly change, your flight can too.
What do I need for the flight to Thimble Islands?
There is so much to sort out for any big adventure, so it's nice to get a bit of help before you set out. Here are a few tips to ensure that you're ready for take off:

  • Travel documents such as e-tickets and some identification will be required. To avoid any unnecessary delays at check-in, make certain your booking is under the exact name, birth date and gender as your government-issued ID.
  • Stock your carry-on bag with activities and snacks and you'll happily pass the time on this medium-haul flight. Wherever possible, get on the airport's Wi-Fi and transfer your favorite podcast or playlist to your device ahead of your journey.
  • Regardless what the season is, airplane cabins are known to get chilly. Bring a sweater on your journey to stay nice and warm.

How do I get cheap first-class/business deals to Thimble Islands?
Smart travelers have a talent for finding first or business-class airfares to Thimble Islands that don't cost an arm and a leg. Follow their example with these handy hints:

  • Be more flexible with your travel dates and wait for sales or exclusive offers on business or first-class airfares.
  • Plenty of budget carriers these days offer outstanding business-class seating for a reasonable price.
  • Take advantage of your airline's rewards program and upgrade your seat. You can also bid for an upgrade in an online auction.

How to get into Thimble Islands from the airport?
Driving is a good option. Hertz, Budget and Avis are three car rental outlets located at Tweed - New Haven Regional Airport (HVN). After picking up a Tweed - New Haven Regional Airport (HVN) car rental, you can whiz directly from HVN airport into downtown Thimble Islands, a distance of 7 miles to the east. Or, if you're planning to book your own set of wheels from the city center, take a look through our Thimble Islands car rentals.
Travel tips for Thimble Islands

  • Stony Creek Museum is one of this buzzing city's best attractions. Stay near the center and visit it whenever you please.
  • You'll find other great sights to stick on your itinerary within an easy driving distance of the center. Organize a car rental, slide behind the wheel and make tracks to Yale University.
  • When you're ready to explore more of the splendors of Connecticut, fill up the gas tank and take a road trip to Hartford. One of the region's other great cities, the possibilities for fun are endless here.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.