Search Cheap Flights to
Middletown

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Middletown Flights as Low as $92

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

Spirit Airlines
Thu, Aug 28 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$92 Roundtrip, found 2 days ago
$92
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $92 found 2 days ago
Breeze Airways
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$93 Roundtrip, found 2 days ago
$93
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $93 found 2 days ago
Spirit Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 2 days ago
$100
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $100 found 2 days ago
Breeze Airways
Fri, Aug 29 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$102 Roundtrip, found 2 days ago
$102
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 29 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $102 found 2 days ago
Breeze Airways
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$103 Roundtrip, found 2 days ago
$103
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $103 found 2 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$105 Roundtrip, found 8 hours ago
$105
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Bradley Intl., returning Sun, Sep 7, priced at $105 found 8 hours ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$106 Roundtrip, found 8 hours ago
$106
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Bradley Intl., returning Sun, Sep 7, priced at $106 found 8 hours ago
Breeze Airways
Fri, Aug 29 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$107 Roundtrip, found 2 days ago
$107
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Fri, Aug 29 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $107 found 2 days ago
Spirit Airlines
Mon, Oct 6 - Mon, Oct 13
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 3 days ago
$108
Roundtrip
found 3 days ago
Select Spirit Airlines flight, departing Mon, Oct 6 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Oct 13, priced at $108 found 3 days ago
Frontier Airlines
Thu, Sep 18 - Thu, Sep 25
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$109 Roundtrip, found 4 days ago
$109
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Thu, Sep 25, priced at $109 found 4 days ago
Breeze Airways
Wed, Aug 13 - Sat, Aug 16
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select Breeze Airways flight, departing Wed, Aug 13 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 16, priced at $135 found 2 days ago
JetBlue Airways
Thu, Aug 14 - Mon, Aug 25
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 11 hours ago
$137
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Thu, Aug 14 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Aug 25, priced at $137 found 11 hours ago
American Airlines
Wed, Oct 8 - Tue, Oct 14
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 3 days ago
$159
Roundtrip
found 3 days ago
Select American Airlines flight, departing Wed, Oct 8 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Oct 14, priced at $159 found 3 days ago
Delta
Thu, Sep 4 - Tue, Sep 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 8 hours ago
$197
Roundtrip
found 8 hours ago
Select Delta flight, departing Thu, Sep 4 from Orlando Intl. to Bradley Intl., returning Tue, Sep 9, priced at $197 found 8 hours ago
United
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$207 Roundtrip, found 2 days ago
$207
Roundtrip
found 2 days ago
Select United flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $207 found 2 days ago
Delta
Wed, Aug 6 - Tue, Aug 12
BZN
Bozeman Yellowstone Intl.
BDL
Bradley Intl.
$643 Roundtrip, found 1 day ago
$643
Roundtrip
found 1 day ago
Select Delta flight, departing Wed, Aug 6 from Bozeman Yellowstone Intl. to Bradley Intl., returning Tue, Aug 12, priced at $643 found 1 day 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 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 $92, 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 $92 right now, why wait?

Middletown Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$92

Last Minute Hotel Deals in Middletown

Inn at Middletown

Inn at Middletown

3.5 out of 5
70 Main Street, Middletown, CT
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 ...
8.8/10 Excellent! (495 reviews)
Good location
"Very nice hotel in great location"

Reviewed on Jul 30, 2025

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Inn at Middletown
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Stay at this 3-star 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! (1,049 reviews)
"Each stuff member was very friendly"

Reviewed on Jul 30, 2025

Get rates
The Capitol Hotel
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! (1,695 reviews)
"Right in the middle of downtown"

Reviewed on Jul 29, 2025

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New Haven Hotel
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! (1,018 reviews)
"The hotel was nice. But the surrounding area outside of the hotel was a little sketchy."

Reviewed on Jul 26, 2025

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Omni New Haven Hotel at Yale
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 (1,003 reviews)
"Good place"

Reviewed on Jul 29, 2025

Get rates
Motel 6 New Haven - Branford, CT
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
351 Pitkin Steet, East Hartford, CT
Stay at this hotel in East Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
9/10 Wonderful! (1,001 reviews)
Great comfortable place to stay
"The staff went out of their way to help me with my disabilities to help me feel safe. I had a great safe shower 😌"

Reviewed on Jul 29, 2025

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Hampton Inn & Suites Hartford/East Hartford
Woodspring Suites Newington - Hartford South

Woodspring Suites Newington - Hartford South

2.5 out of 5
712 Cedar Street, Newington, CT
Stay at this hotel in Newington. Enjoy free WiFi and free parking. Popular attractions Iwo Jima Survivors Memorial Park and Westfarms Mall are located ...
7.6/10 Good! (140 reviews)
Friendly Staff
"Clean and great location to CCSU. Excellent and friendly staff!"

Reviewed on Jul 31, 2025

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Woodspring Suites Newington - Hartford South
The Blake Hotel

The Blake Hotel

4 out of 5
9 High Street, New Haven, CT
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff ...
9.4/10 Exceptional! (1,003 reviews)
Beautiful Hotel in Great Location
"We very much enjoyed the Blake and intend to return when back in NH. Special thanks to Lori (Laurie?) at the desk, who always was especially pleasant and helpful. We loved the kitchenette, with dishwasher, although china is sparse. Also appreciated the eco friendly attempts, like no plastic cups ..."

Reviewed on Jul 31, 2025

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The Blake Hotel
See all 1,159 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.