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Windsor

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Windsor Flights as Low as $56

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

Frontier Airlines
Wed, Mar 4 - Mon, Mar 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Mar 4 from Orlando Intl. to Bradley Intl., returning Mon, Mar 9, priced at $56 found 2 hours ago
Frontier Airlines
Wed, Mar 4 - Sun, Mar 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$66 Roundtrip, found 2 days ago
$66
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Mar 4 from Orlando Intl. to Bradley Intl., returning Sun, Mar 8, priced at $66 found 2 days ago
Frontier Airlines
Thu, Mar 12 - Sun, Mar 15
MCO
Orlando Intl.
BDL
Bradley Intl.
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Mar 12 from Orlando Intl. to Bradley Intl., returning Sun, Mar 15, priced at $72 just found
Frontier Airlines
Thu, Feb 5 - Sun, Feb 8
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$74 Roundtrip, found 1 day ago
$74
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Feb 5 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sun, Feb 8, priced at $74 found 1 day ago
Frontier Airlines
Tue, Mar 3 - Sun, Mar 8
MCO
Orlando Intl.
BDL
Bradley Intl.
$77 Roundtrip, found 6 hours ago
$77
Roundtrip
found 6 hours ago
Select Frontier Airlines flight, departing Tue, Mar 3 from Orlando Intl. to Bradley Intl., returning Sun, Mar 8, priced at $77 found 6 hours ago
JetBlue Airways
Wed, Mar 4 - Tue, Mar 10
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$120 Roundtrip, found 2 days ago
$120
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Mar 4 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Tue, Mar 10, priced at $120 found 2 days ago
Breeze Airways
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$122 Roundtrip, found 12 hours ago
$122
Roundtrip
found 12 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $122 found 12 hours ago
Frontier Airlines
Thu, Feb 12 - Tue, Feb 17
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$146 Roundtrip, found 2 days ago
$146
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Feb 12 from Luis Munoz Marin Intl. to Bradley Intl., returning Tue, Feb 17, priced at $146 found 2 days ago
American Airlines
Wed, Mar 4 - Mon, Mar 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 2 hours ago
$159
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Wed, Mar 4 from Orlando Intl. to Bradley Intl., returning Mon, Mar 9, priced at $159 found 2 hours ago
JetBlue Airways
Fri, Feb 13 - Tue, Feb 17
PBI
Palm Beach Intl.
BDL
Bradley Intl.
$168 Roundtrip, found 10 hours ago
$168
Roundtrip
found 10 hours ago
Select JetBlue Airways flight, departing Fri, Feb 13 from Palm Beach Intl. to Bradley Intl., returning Tue, Feb 17, priced at $168 found 10 hours ago
United
Wed, Mar 4 - Mon, Mar 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$178 Roundtrip, found 2 hours ago
$178
Roundtrip
found 2 hours ago
Select United flight, departing Wed, Mar 4 from Orlando Intl. to Bradley Intl., returning Mon, Mar 9, priced at $178 found 2 hours ago
Delta
Wed, Mar 4 - Mon, Mar 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Mar 4 from Orlando Intl. to Bradley Intl., returning Mon, Mar 9, priced at $197 found 2 hours ago
Frontier Airlines
Fri, Feb 6 - Sun, Feb 8
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$290 Roundtrip, found 5 hours ago
$290
Roundtrip
found 5 hours ago
Select Frontier Airlines flight, departing Fri, Feb 6 from Charlotte-Douglas Intl. to Bradley Intl., returning Sun, Feb 8, priced at $290 found 5 hours ago
Frontier Airlines
Sat, Jan 31 - Thu, Feb 5
IAH
George Bush Intercontinental
BDL
Bradley Intl.
$300 Roundtrip, found 11 hours ago
$300
Roundtrip
found 11 hours ago
Select Frontier Airlines flight, departing Sat, Jan 31 from George Bush Intercontinental to Bradley Intl., returning Thu, Feb 5, priced at $300 found 11 hours ago
Delta
Sat, May 9 - Tue, May 12
BIL
Logan Intl.
BDL
Bradley Intl.
$309 Roundtrip, found 12 hours ago
$309
Roundtrip
found 12 hours ago
Select Delta flight, departing Sat, May 9 from Logan Intl. to Bradley Intl., returning Tue, May 12, priced at $309 found 12 hours ago
Alaska Airlines
Fri, May 8 - Sun, May 10
BIL
Logan Intl.
BDL
Bradley Intl.
$640 Roundtrip, found 12 hours ago
$640
Roundtrip
found 12 hours ago
Select Alaska Airlines flight, departing Fri, May 8 from Logan Intl. to Bradley Intl., returning Sun, May 10, priced at $640 found 12 hours ago

Cheap Flights to Windsor

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

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

Frequently Asked Questions About flights to Windsor

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

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 Windsor are in March, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Windsor?

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 Windsor.

What airport is best to fly into Windsor?

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

How much are flights to Windsor?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Windsor on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $56, 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 Windsor?

The trick to saving a stack of cash on your flight to Windsor? 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 $56 right now, why wait?

Windsor Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$56

Last Minute Hotel Deals in Windsor

Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
100 Dunfey Ln Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (694 reviews)
Would definitely stay there again.

Reviewed on Jan 19, 2026

Get rates
Residence Inn by Marriott Hartford/Windsor
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
2168 Poquonock Ave Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (1,000 reviews)
Second time here, breakfast was always fresh, pool was clean and staff was friendly. My son and I loved the hot chocolate bar with the coffee and tea all day. It was such a nice touch visiting around the holidays

Reviewed on Dec 31, 2025

Get rates
Hampton Inn Hartford/Airport
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,000 reviews)
Staff were pleasant and informative upon arrival. The room was just as pictured. Very spacious and clean. A true five star hotel!

Reviewed on Jan 20, 2026

Get rates
HYATT house Hartford North/Windsor
Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (1,002 reviews)
Dana the front desk associate was sooo nice and helpful!

Reviewed on Jan 21, 2026

Get rates
Marriott Hartford/Windsor Airport
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
555 Corporate Dr Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,000 reviews)
Clean room, friendly staff. Recommended.

Reviewed on Jan 11, 2026

Get rates
Hilton Garden Inn Hartford North/Bradley Int'l Airport
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! (1,153 reviews)
Friendly staff, easy and typical buffet breakfast. Walking distance to all major downtown Hartford attractions. Will use again if needed.

Reviewed on Jan 19, 2026

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The Capitol Hotel
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way Springfield MA
Stay at this hotel in Springfield. Enjoy free parking, an outdoor pool, and 8 restaurants. Our guests praise the helpful staff and the convenient parking in ...
8.8/10 Excellent! (1,468 reviews)
Boutique and very clean

Reviewed on Jan 22, 2026

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MGM Springfield
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! (1,208 reviews)
There was little water pressure in the bathroom shower. The rooms need a deep clean, food stain on the walls. Beds were very comfortable and it was quiet.

Reviewed on Jan 20, 2026

Get rates
Holiday Inn Express Southington by IHG
See all 749 properties in Windsor
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.

Top Hotels With Free Airport Shuttle

Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

3 out of 5
1 Day Hill Rd Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our ...
8.8/10 Excellent! (999 reviews)
One of the cleanest and organized hotel I have been too.

Reviewed on Jan 10, 2026

Get rates
Courtyard By Marriott Hartford/Windsor Airport
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
2168 Poquonock Ave Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9/10 Wonderful! (1,000 reviews)
Second time here, breakfast was always fresh, pool was clean and staff was friendly. My son and I loved the hot chocolate bar with the coffee and tea all day. It was such a nice touch visiting around the holidays

Reviewed on Dec 31, 2025

Get rates
Hampton Inn Hartford/Airport
Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free parking, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful ...
8.4/10 Very Good! (1,002 reviews)
Dana the front desk associate was sooo nice and helpful!

Reviewed on Jan 21, 2026

Get rates
Marriott Hartford/Windsor Airport
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
555 Corporate Dr Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.6/10 Excellent! (1,000 reviews)
Clean room, friendly staff. Recommended.

Reviewed on Jan 11, 2026

Get rates
Hilton Garden Inn Hartford North/Bradley Int'l Airport
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,000 reviews)
Staff were pleasant and informative upon arrival. The room was just as pictured. Very spacious and clean. A true five star hotel!

Reviewed on Jan 20, 2026

Get rates
HYATT house Hartford North/Windsor
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
100 Dunfey Ln Windsor CT
Book a stay at this business-friendly hotel in Windsor. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the helpful staff in our reviews. ...
8.2/10 Very Good! (694 reviews)
Would definitely stay there again.

Reviewed on Jan 19, 2026

Get rates
Residence Inn by Marriott Hartford/Windsor
See all 749 properties in Windsor
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.