Search Cheap Flights to
Middletown

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Middletown Flights as Low as $77

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

Avelo Airlines
Thu, Jun 19 - Sun, Jun 22
BWI
Baltimore Washington Intl. Thurgood Marshall
HVN
Tweed - New Haven Regional
$77 Roundtrip, found 22 hours ago
$77
Roundtrip
found 22 hours ago
Select Avelo Airlines flight, departing Thu, Jun 19 from Baltimore Washington Intl. Thurgood Marshall to Tweed - New Haven Regional, returning Sun, Jun 22, priced at $77 found 22 hours ago
Avelo Airlines
Thu, Jul 3 - Sun, Jul 6
BWI
Baltimore Washington Intl. Thurgood Marshall
HVN
Tweed - New Haven Regional
$84 Roundtrip, found 23 hours ago
$84
Roundtrip
found 23 hours ago
Select Avelo Airlines flight, departing Thu, Jul 3 from Baltimore Washington Intl. Thurgood Marshall to Tweed - New Haven Regional, returning Sun, Jul 6, priced at $84 found 23 hours ago
JetBlue Airways
Tue, May 20 - Tue, May 27
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$141 Roundtrip, found 19 hours ago
$141
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Southwest Florida Intl. to Bradley Intl., returning Tue, May 27, priced at $141 found 19 hours ago
JetBlue Airways
Wed, May 21 - Tue, May 27
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$144 Roundtrip, found 19 hours ago
$144
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Wed, May 21 from Southwest Florida Intl. to Bradley Intl., returning Tue, May 27, priced at $144 found 19 hours ago
American Airlines
Tue, Aug 5 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$145 Roundtrip, found 10 hours ago
$145
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Aug 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $145 found 10 hours ago
JetBlue Airways
Tue, May 20 - Wed, May 21
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 19 hours ago
$161
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Southwest Florida Intl. to Bradley Intl., returning Wed, May 21, priced at $161 found 19 hours ago
Breeze Airways
Wed, Jul 30 - Sun, Aug 3
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$162 Roundtrip, found 11 hours ago
$162
Roundtrip
found 11 hours ago
Select Breeze Airways flight, departing Wed, Jul 30 from Southwest Florida Intl. to Bradley Intl., returning Sun, Aug 3, priced at $162 found 11 hours ago
JetBlue Airways
Thu, May 22 - Sat, May 24
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$164 Roundtrip, found 19 hours ago
$164
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Thu, May 22 from Southwest Florida Intl. to Bradley Intl., returning Sat, May 24, priced at $164 found 19 hours ago
American Airlines
Tue, Aug 5 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$165 Roundtrip, found 10 hours ago
$165
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Tue, Aug 5 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $165 found 10 hours ago
Frontier Airlines
Sat, May 31 - Sat, Jun 7
BWI
Baltimore Washington Intl. Thurgood Marshall
BDL
Bradley Intl.
$172 Roundtrip, found 17 hours ago
$172
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Sat, May 31 from Baltimore Washington Intl. Thurgood Marshall to Bradley Intl., returning Sat, Jun 7, priced at $172 found 17 hours ago
Breeze Airways
Fri, May 23 - Sun, May 25
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$176 Roundtrip, found 19 hours ago
$176
Roundtrip
found 19 hours ago
Select Breeze Airways flight, departing Fri, May 23 from Southwest Florida Intl. to Bradley Intl., returning Sun, May 25, priced at $176 found 19 hours ago
Spirit Airlines
Wed, Jul 30 - Sun, Aug 3
RSW
Southwest Florida Intl.
BDL
Bradley Intl.
$182 Roundtrip, found 11 hours ago
$182
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Wed, Jul 30 from Southwest Florida Intl. to Bradley Intl., returning Sun, Aug 3, priced at $182 found 11 hours ago
Bargain Flight
Sat, May 17 - Wed, May 28
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$187 Roundtrip, found 13 hours ago
$187
Roundtrip
found 13 hours ago
Select Bargain Flight flight, departing Sat, May 17 from Charlotte-Douglas Intl. to Bradley Intl., returning Wed, May 28, priced at $187 found 13 hours ago
Delta
Sat, Aug 2 - Tue, Aug 12
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 10 hours ago
$197
Roundtrip
found 10 hours ago
Select Delta flight, departing Sat, Aug 2 from Charlotte-Douglas Intl. to Bradley Intl., returning Tue, Aug 12, priced at $197 found 10 hours ago
Spirit Airlines
Sat, May 31 - Sun, Jun 8
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$214 Roundtrip, found 5 days ago
$214
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sat, May 31 from Luis Munoz Marin Intl. to Bradley Intl., returning Sun, Jun 8, priced at $214 found 5 days ago
Breeze Airways
Sat, Jun 7 - Mon, Jun 16
RSW
Southwest Florida Intl.
HVN
Tweed - New Haven Regional
$356 Roundtrip, found 4 days ago
$356
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Sat, Jun 7 from Southwest Florida Intl. to Tweed - New Haven Regional, returning Mon, Jun 16, priced at $356 found 4 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 June, 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 $77, 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 $77 right now, why wait?

Middletown Flight Information
Destination airport
Tweed - New Haven Regional
Destination airport IATA code
HVN
Roundtrip price
$77

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 $241 per night from May 8 to May 9
$241
includes taxes & fees
May 8 - May 9
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! (462 reviews)
"Good location to walk around or hop on the highway."

Reviewed on Apr 22, 2025

Inn at Middletown
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
The price is $146 per night from May 4 to May 5
$146
includes taxes & fees
May 4 - May 5
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 ...
"Overall clean with nice staff. Not fancy but a good night's sleep."

Reviewed on Apr 28, 2025

New Haven Hotel
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 May 4 to May 5
$246
includes taxes & fees
May 4 - May 5
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! (1,001 reviews)
"Spa was fantastic, rooms are nothing extravagant but clean and well maintained. Everyone was polite, great stay"

Reviewed on Apr 29, 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 May 14 to May 15
$165
includes taxes & fees
May 14 - May 15
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 ...
"Close to Yale University. Great restaurant."

Reviewed on Apr 25, 2025

Omni New Haven Hotel at Yale
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
The price is $108 per night from May 6 to May 7
$108
includes taxes & fees
May 6 - May 7
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! (1,007 reviews)
"Excellent customer service"

Reviewed on Apr 22, 2025

Clarion Inn
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 $117 per night from May 4 to May 5
$117
includes taxes & fees
May 4 - May 5
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! (1,001 reviews)
One Night Turned Into Four
"I stayed at this location with my son the night before a conference in downtown Hartford. The hotel was well kept and staff were welcoming. We had anticipated on staying at another hotel downtown for the rest of our stay but unfortunately did not feel safe in that neighborhood. We immediately returned ..."

Reviewed on Apr 29, 2025

Holiday Inn Express Southington by IHG
Courtyard by Marriott Waterbury Downtown
Courtyard by Marriott Waterbury Downtown
3 out of 5
63 Grand St, Waterbury, CT
The price is $125 per night from May 1 to May 2
$125
includes taxes & fees
May 1 - May 2
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! (1,000 reviews)

Reviewed on Apr 28, 2025

Courtyard by Marriott Waterbury Downtown
The Goodwin Hotel
The Goodwin Hotel
3.5 out of 5
1 Haynes St, Hartford, CT
The price is $217 per night from May 11 to May 12
$217
includes taxes & fees
May 11 - May 12
Stay at this 3.5-star hotel in Hartford. Enjoy free WiFi, a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,006 reviews)
"I thought"

Reviewed on Apr 28, 2025

The Goodwin Hotel
See all 1,173 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.