Search Cheap Flights to
Thimble Islands

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Thimble Islands Flights as Low as $111

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

Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Breeze Airways
Avelo Airlines
Breeze Airways
Breeze Airways
Breeze Airways
Avelo Airlines
Avelo Airlines

Cheap Flights to Thimble Islands

Fall in love at first flight with your vacation to Thimble Islands by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Thimble Islands on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Thimble Islands, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Thimble Islands

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Thimble Islands with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the HVN airport.

What is the cheapest month to fly to Thimble Islands?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Thimble Islands are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Thimble Islands?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Thimble Islands.

What airport is best to fly into Thimble Islands?

When you’re planning your trip to Thimble Islands, convenience is the name of the game. Luckily, Thimble Islands Tweed - New Haven Regional Airport is nearby so you can deplane and get going on checking off everything on your Thimble Islands must-do list.

How much are flights to Thimble Islands?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Thimble Islands on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $111, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Thimble Islands?

The trick to saving a stack of cash on your flight to Thimble Islands? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $111 right now, why wait?

Thimble Islands Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$110

Last Minute Hotel Deals in Thimble Islands

New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,598 reviews)
"Overall, the hotel was amazing to stay at but my one gripe was that the TV remote was very sticky/dirty to touch which was something I never really experienced before and was a bit concerned. But other than that I had a great time and my overall experience was exceptional"

Reviewed on Jun 15, 2025

New Haven Hotel
Motel 6 New Haven - Branford, CT
Motel 6 New Haven - Branford, CT
2 out of 5
320 E Main St, Branford, CT
Stay at this motel in Branford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
6.8/10 (1,004 reviews)
"N/A"

Reviewed on May 31, 2025

Motel 6 New Haven - Branford, CT
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Book a stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.4/10 Good! (1,006 reviews)
"nice service"

Reviewed on Jun 13, 2025

Clarion Inn
Red Roof Inn Milford - New Haven
Red Roof Inn Milford - New Haven
2 out of 5
10 Rowe Ave, Milford, CT
Stay at this hotel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the clean rooms in our reviews. Popular attractions ...
7/10 Good! (1,004 reviews)
"Decent but old"

Reviewed on Jun 10, 2025

Red Roof Inn Milford - New Haven
Motel 6 Milford, CT
Motel 6 Milford, CT
2 out of 5
111 Schoolhouse Road, Milford, CT
Book a stay at this business-friendly motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Silver Sands State Park ...
6/10 (1,004 reviews)
"Check in was easy and fast. Room was good, parking easy. Checkout was easy too!"

Reviewed on Jun 16, 2025

Motel 6 Milford, CT
La Quinta Inn & Suites by Wyndham New Haven
La Quinta Inn & Suites by Wyndham New Haven
3 out of 5
400 Sargent Dr, New Haven, CT
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
5.8/10 (1,014 reviews)
"Staff were excellent. Neighbors were a bit noisy. Breakfast was good. Elevators were being repaired so staff had to accompany us to manually use the elevator. A little inconvenient but not horrible. Good price for a clean room."

Reviewed on Jun 11, 2025

La Quinta Inn & Suites by Wyndham New Haven
Best Western Executive Hotel Of New Haven - West Haven
Best Western Executive Hotel Of New Haven - West Haven
2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
7.6/10 Good! (1,146 reviews)
"Overnight stay. Shower was nice. Bed was comfortable. Convenient location to I95. Was able to walk to Dunkin and 7-eleven."

Reviewed on Jun 14, 2025

Best Western Executive Hotel Of New Haven - West Haven
Omni New Haven Hotel at Yale
Omni New Haven Hotel at Yale
4 out of 5
155 Temple St, New Haven, CT
Stay at this 4-star business-friendly hotel in New Haven. Enjoy 2 restaurants, breakfast (surcharge), and room service. Our guests praise the helpful staff and ...
8.2/10 Very Good! (1,001 reviews)
"Amazing staff."

Reviewed on Jun 13, 2025

Omni New Haven Hotel at Yale
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.