Search Cheap Flights to
Middletown

Search 400 airlines and 321,000 hotels worldwide.

Stop Planning & Start Exploring

FREE 24 hour cancellation on most flights

Middletown Flights as Low as $183

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

Breeze Airways
Breeze Airways
Breeze Airways
Delta
JetBlue Airways
Breeze Airways
Breeze Airways
Delta
United
American Airlines
Avelo Airlines
Breeze Airways
JetBlue Airways
Delta
Breeze Airways
Avelo Airlines

Cheap Flights to Middletown

Fall in love at first flight with your vacation to Middletown 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 Middletown on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Middletown

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Middletown 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 HFD airport.

What is the cheapest month to fly to Middletown?

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 Middletown are in August, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Middletown?

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 Middletown.

What airport is best to fly into Middletown?

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

How much are flights to Middletown?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Middletown on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $183, 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 Middletown?

The trick to saving a stack of cash on your flight to Middletown? 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 $183 right now, why wait?

Middletown Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$183

Last Minute Hotel Deals in Middletown

Inn at Middletown

Inn at Middletown

3.5 out of 5
70 Main Street Middletown CT
Book a stay at this business-friendly hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
9/10 Wonderful! (619 reviews)
"Nice restaurant great staff and good rooms"

Reviewed on Jun 26, 2026

Inn at Middletown
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and ...
9.2/10 Wonderful! (2,199 reviews)
"Nice location"

Reviewed on Jun 26, 2026

New Haven Hotel
Motel 6 Wethersfield, CT - Hartford

Motel 6 Wethersfield, CT - Hartford

2 out of 5
1341 Silas Deane Hwy Wethersfield CT
Stay at this motel in Wethersfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7/10 Good! (1,196 reviews)
"Stayed at room while volunteering at the Traveler's Golf Tournament. Room had dirty, sticky floor, only one towel, no hangers, toilet seat was filthy and the sink faucet was falling off. Upon checking in a parking pass was given to me to put on the dashboard of my car. Was asked if anyone else was ..."

Reviewed on Jun 26, 2026

Motel 6 Wethersfield, CT - Hartford
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
1525 Boston Post Road Westbrook CT
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
"we stayed for weekend had a great time beautiful room comfortable bed amazing spa tub restraunt food and bar convenient & delicious staff very nice"

Reviewed on Jun 25, 2026

Water's Edge Resort & Spa
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St New Haven CT
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful ...
8.6/10 Excellent! (1,035 reviews)
"I was surprised by how dated and small the room was at this higher-end hotel. Though I reserved a room with a king-sized bed, the bed was a full or queen. The bathroom lighting was so dim that I had to use the ceiling heating lamp to see better. The mini-fridge was unplugged upon arrival and smelled ..."

Reviewed on Jun 27, 2026

Omni New Haven Hotel at Yale
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (1,002 reviews)
"staff and parking"

Reviewed on Jun 22, 2026

Pier Blue Inn Old Saybrook - Essex
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Book a stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free WiFi, and a 24-hour fitness center. Our guests praise the breakfast and the ...
7.4/10 Good! (1,395 reviews)
"The Capitol Hotel was more like a youth hostel than a hotel … and that’s fine except that it charges like a mid-range hotel. We were greeted by a group of homeless folks in the parking lot, including one who approached us to ask for money. Usually not an issue, but very uncomfortable when entering ..."

Reviewed on Jun 25, 2026

The Capitol Hotel
Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

2.5 out of 5
2260 Whitney Ave Hamden CT
Book a stay at this business-friendly hotel in Hamden. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast in our reviews. Popular ...
6.8/10 (1,007 reviews)
"Please don't stay here. I had booked through Expedia -- I booked a room with two queen beds. They threw me in a room with one king and when I complained blamed it on Expedia. I made it work but very upsetting. I also called the front desk to ask why the Wifi wasn't working and got told "Well the ..."

Reviewed on Jun 26, 2026

Hamden Hotel and Suites – Hamden New Haven
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.