Search Cheap Flights to
Middletown

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Middletown Flights as Low as $90

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

Spirit Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$90 Roundtrip, found 1 hour ago
$90
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $90 found 1 hour ago
Frontier Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$93 Roundtrip, found 1 hour ago
$93
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $93 found 1 hour ago
Spirit Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$98 Roundtrip, found 1 hour ago
$98
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $98 found 1 hour ago
Frontier Airlines
Sat, May 3 - Wed, May 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 4 hours ago
$102
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, May 3 from Orlando Intl. to Bradley Intl., returning Wed, May 7, priced at $102 found 4 hours ago
Spirit Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$105 Roundtrip, found 1 hour ago
$105
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $105 found 1 hour ago
Frontier Airlines
Sat, May 3 - Sun, May 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 8 hours ago
$108
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Sat, May 3 from Orlando Intl. to Bradley Intl., returning Sun, May 4, priced at $108 found 8 hours ago
Spirit Airlines
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$113 Roundtrip, found 1 hour ago
$113
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $113 found 1 hour ago
Breeze Airways
Sat, Jun 14 - Tue, Jul 1
MCO
Orlando Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 2 hours ago
$132
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Sat, Jun 14 from Orlando Intl. to Bradley Intl., returning Tue, Jul 1, priced at $132 found 2 hours ago
JetBlue Airways
Sat, May 3 - Wed, May 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$155 Roundtrip, found 4 hours ago
$155
Roundtrip
found 4 hours ago
Select JetBlue Airways flight, departing Sat, May 3 from Orlando Intl. to Bradley Intl., returning Wed, May 7, priced at $155 found 4 hours ago
Spirit Airlines
Sun, May 18 - Sun, May 25
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$183 Roundtrip, found 21 hours ago
$183
Roundtrip
found 21 hours ago
Select Spirit Airlines flight, departing Sun, May 18 from George Bush Intercontinental to Bradley Intl., returning Sun, May 25, priced at $183 found 21 hours ago
Delta
Thu, May 1 - Tue, May 6
MCO
Orlando Intl.
BDL
Bradley Intl.
$200 Roundtrip, found 1 hour ago
$200
Roundtrip
found 1 hour ago
Select Delta flight, departing Thu, May 1 from Orlando Intl. to Bradley Intl., returning Tue, May 6, priced at $200 found 1 hour ago
United
Sat, May 3 - Wed, May 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$237 Roundtrip, found 4 hours ago
$237
Roundtrip
found 4 hours ago
Select United flight, departing Sat, May 3 from Orlando Intl. to Bradley Intl., returning Wed, May 7, priced at $237 found 4 hours ago
American Airlines
Sat, May 3 - Wed, May 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$237 Roundtrip, found 4 hours ago
$237
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Sat, May 3 from Orlando Intl. to Bradley Intl., returning Wed, May 7, priced at $237 found 4 hours ago
Bargain Flight
Sat, May 10 - Tue, May 13
MCI
Kansas City Intl.
BDL
Bradley Intl.
$257 Roundtrip, found 1 day ago
$257
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, May 10 from Kansas City Intl. to Bradley Intl., returning Tue, May 13, priced at $257 found 1 day ago
Air Canada
Sun, May 11 - Tue, May 13
YYZ
Pearson Intl.
BDL
Bradley Intl.
$380 Roundtrip, found 1 day ago
$380
Roundtrip
found 1 day ago
Select Air Canada flight, departing Sun, May 11 from Pearson Intl. to Bradley Intl., returning Tue, May 13, priced at $380 found 1 day ago
WestJet
Tue, Jun 17 - Wed, Jun 18
YYZ
Pearson Intl.
BDL
Bradley Intl.
$461 Roundtrip, found 3 days ago
$461
Roundtrip
found 3 days ago
Select WestJet flight, departing Tue, Jun 17 from Pearson Intl. to Bradley Intl., returning Wed, Jun 18, priced at $461 found 3 days ago

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 May, 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 15 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 $90, 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 $90 right now, why wait?

Middletown Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$89

Last Minute Hotel Deals in Middletown

Inn at Middletown
Inn at Middletown
3.5 out of 5
70 Main Street, Middletown, CT
The price is $266 per night from Apr 20 to Apr 21
$266
includes taxes & fees
Apr 20 - Apr 21
Stay at this 3.5-star business-friendly hotel in Middletown. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
9/10 Wonderful! (455 reviews)
"The best place to stay in Middletown. Only downside is the parking."

Reviewed on Apr 5, 2025

Inn at Middletown
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
The price is $136 per night from Apr 27 to Apr 28
$136
includes taxes & fees
Apr 27 - Apr 28
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! (1,493 reviews)
"My parents had a wonderful stay at the New Haven, unfortunately the restaurant was closed but it’s in an awesome location in the middle of lots of dining options. There is a nightclub close by, so depending on where your room is you may hear the music at night. The customer service was amazing, Zihima ..."

Reviewed on Apr 12, 2025

New Haven Hotel
Holiday Inn Express Southington by IHG
Holiday Inn Express Southington by IHG
2.5 out of 5
120 Laning St, Southington, CT
The price is $109 per night from Apr 20 to Apr 21
$109
includes taxes & fees
Apr 20 - Apr 21
Book a stay at this business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,013 reviews)
"The check in and check out was seamless. Staff was nice. Rooms were clean and comfortable."

Reviewed on Apr 14, 2025

Holiday Inn Express Southington by IHG
Water's Edge Resort & Spa
Water's Edge Resort & Spa
3.5 out of 5
1525 Boston Post Road, Westbrook, CT
The price is $246 per night from Apr 16 to Apr 17
$246
includes taxes & fees
Apr 16 - Apr 17
Stay at this 3.5-star beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the property condition ...
8.6/10 Excellent! (1,003 reviews)
"Staff is always very receptive and cordial!"

Reviewed on Apr 10, 2025

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
The price is $165 per night from Apr 29 to Apr 30
$165
includes taxes & fees
Apr 29 - Apr 30
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! (1,008 reviews)
"very clean and central"

Reviewed on Apr 11, 2025

Omni New Haven Hotel at Yale
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
The price is $99 per night from Apr 27 to Apr 28
$99
includes taxes & fees
Apr 27 - Apr 28
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! (1,005 reviews)
"It was great"

Reviewed on Apr 13, 2025

Clarion Inn
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
The price is $102 per night from Apr 16 to Apr 17
$102
includes taxes & fees
Apr 16 - Apr 17
Stay at this hotel in Waterbury. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8.4/10 Very Good! (1,003 reviews)
Best front desk manager
"Front desk manager was amazing. Best customer service!! She was amazing and hard working."

Reviewed on Apr 13, 2025

Courtyard by Marriott Waterbury Downtown
Motel 6 Wethersfield, CT - Hartford
Motel 6 Wethersfield, CT - Hartford
2 out of 5
1341 Silas Deane Hwy, Wethersfield, CT
The price is $75 per night from Apr 20 to Apr 21
$75
includes taxes & fees
Apr 20 - Apr 21
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. ...
6.4/10 (1,002 reviews)
"Very lovely people"

Reviewed on Apr 4, 2025

Motel 6 Wethersfield, CT - Hartford
See all 1,168 properties in Middletown
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.