Search Cheap Flights to
Middletown

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Middletown Flights as Low as $86

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

Frontier Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$86 Roundtrip, found 4 hours ago
$86
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $86 found 4 hours ago
Spirit Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$87 Roundtrip, found 4 hours ago
$87
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $87 found 4 hours ago
Spirit Airlines
Fri, Sep 5 - Fri, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$93 Roundtrip, found 1 day ago
$93
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Fri, Sep 5 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Sep 12, priced at $93 found 1 day ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$97 Roundtrip, found 5 days ago
$97
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Bradley Intl., returning Sun, Sep 7, priced at $97 found 5 days ago
Breeze Airways
Fri, Sep 5 - Sun, Sep 7
MCO
Orlando Intl.
BDL
Bradley Intl.
$99 Roundtrip, found 5 days ago
$99
Roundtrip
found 5 days ago
Select Breeze Airways flight, departing Fri, Sep 5 from Orlando Intl. to Bradley Intl., returning Sun, Sep 7, priced at $99 found 5 days ago
Frontier Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$100 Roundtrip, found 4 hours ago
$100
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $100 found 4 hours ago
Frontier Airlines
Sat, Aug 30 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$106 Roundtrip, found 4 hours ago
$106
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Sat, Aug 30 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $106 found 4 hours ago
Spirit Airlines
Thu, Aug 28 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$107 Roundtrip, found 2 hours ago
$107
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $107 found 2 hours ago
Spirit Airlines
Thu, Aug 28 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$108 Roundtrip, found 2 hours ago
$108
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Aug 28 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $108 found 2 hours ago
Frontier Airlines
Thu, Sep 18 - Thu, Sep 25
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 9 hours ago
$122
Roundtrip
found 9 hours ago
Select Frontier Airlines flight, departing Thu, Sep 18 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Thu, Sep 25, priced at $122 found 9 hours ago
Breeze Airways
Fri, Oct 10 - Mon, Oct 13
CMH
John Glenn Columbus Intl.
BDL
Bradley Intl.
$123 Roundtrip, found 1 day ago
$123
Roundtrip
found 1 day ago
Select Breeze Airways flight, departing Fri, Oct 10 from John Glenn Columbus Intl. to Bradley Intl., returning Mon, Oct 13, priced at $123 found 1 day ago
JetBlue Airways
Mon, Oct 27 - Sun, Nov 2
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 6 days ago
$167
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Mon, Oct 27 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Sun, Nov 2, priced at $167 found 6 days ago
American Airlines
Fri, Aug 29 - Sun, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select American Airlines flight, departing Fri, Aug 29 from Orlando Intl. to Bradley Intl., returning Sun, Aug 31, priced at $190 found 1 day ago
United
Fri, Sep 5 - Fri, Sep 12
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$190 Roundtrip, found 1 day ago
$190
Roundtrip
found 1 day ago
Select United flight, departing Fri, Sep 5 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Fri, Sep 12, priced at $190 found 1 day ago
Delta
Tue, Sep 9 - Tue, Sep 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 4 days ago
$197
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Sep 9 from Orlando Intl. to Bradley Intl., returning Tue, Sep 9, priced at $197 found 4 days ago
Breeze Airways
Fri, Aug 29 - Sat, Aug 30
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$251 Roundtrip, found 17 hours ago
$251
Roundtrip
found 17 hours ago
Select Breeze Airways flight, departing Fri, Aug 29 from Orlando Intl. to Tweed - New Haven Regional, returning Sat, Aug 30, priced at $251 found 17 hours 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 $86, 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 $86 right now, why wait?

Middletown Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$111

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! (496 reviews)
"Charming hotel conveniently located in walkable Middletown"

Reviewed on Aug 14, 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! (1,002 reviews)
"So originally we were booked to stay at the Goodwin Hotel about two minutes away. Got there and our room wasn’t ready! We had 1 hour to get ready for our friend’s wedding. I went on Expedia app, searched what was available in the area and The Capitol Hotel popped up. Room was HALF THE PRICE from ..."

Reviewed on Aug 14, 2025

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The Capitol Hotel
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
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! (1,065 reviews)
"It was walking distance to Thompson’s point where the music festival I went to see was being held. The staff from the front desk to cleaning staff, were all very friendly. More hooks and/or towel bars in the bathroom. Other than the shelf/rack that all the towels were stored on that is IN THE SHOWER ..."

Reviewed on Aug 15, 2025

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Holiday Inn Express Southington by IHG
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)
"Close to Yale campus"

Reviewed on Aug 14, 2025

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Omni New Haven Hotel at Yale
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! (1,715 reviews)
"."

Reviewed on Aug 14, 2025

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New Haven Hotel
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! (1,001 reviews)
"Staff are"

Reviewed on Aug 13, 2025

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Clarion Inn
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! (1,003 reviews)
"Staff were nice and professional. Room was very clean. Would stay there again if in that area"

Reviewed on Aug 14, 2025

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Hampton Inn & Suites Hartford/East Hartford
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! (1,004 reviews)
"Loved the spacious room and the rooftop bar."

Reviewed on Aug 14, 2025

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The Blake Hotel
See all 1,155 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.