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Windsor

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Windsor Flights as Low as $159

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

Breeze Airways
Wed, Aug 12 - Mon, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 7 hours ago
$159
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Mon, Aug 31, priced at $159 found 7 hours ago
Breeze Airways
Wed, Aug 12 - Mon, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$164 Roundtrip, found 7 hours ago
$164
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Mon, Aug 31, priced at $164 found 7 hours ago
Frontier Airlines
Wed, Sep 2 - Mon, Sep 14
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$166 Roundtrip, found 10 hours ago
$166
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Wed, Sep 2 from Luis Munoz Marin Intl. to Bradley Intl., returning Mon, Sep 14, priced at $166 found 10 hours ago
Frontier Airlines
Wed, Aug 12 - Wed, Aug 26
MCO
Orlando Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 2 days ago
$167
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Aug 26, priced at $167 found 2 days ago
Breeze Airways
Wed, Aug 12 - Mon, Aug 31
MCO
Orlando Intl.
BDL
Bradley Intl.
$169 Roundtrip, found 7 hours ago
$169
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Mon, Aug 31, priced at $169 found 7 hours ago
Breeze Airways
Wed, Aug 12 - Wed, Sep 2
MCO
Orlando Intl.
BDL
Bradley Intl.
$171 Roundtrip, found 7 hours ago
$171
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Wed, Aug 12 from Orlando Intl. to Bradley Intl., returning Wed, Sep 2, priced at $171 found 7 hours ago
Breeze Airways
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$177 Roundtrip, found 15 hours ago
$177
Roundtrip
found 15 hours ago
Select Breeze Airways flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $177 found 15 hours ago
JetBlue Airways
Tue, Aug 11 - Wed, Aug 26
TPA
Tampa Intl.
BDL
Bradley Intl.
$208 Roundtrip, found 11 hours ago
$208
Roundtrip
found 11 hours ago
Select JetBlue Airways flight, departing Tue, Aug 11 from Tampa Intl. to Bradley Intl., returning Wed, Aug 26, priced at $208 found 11 hours ago
Frontier Airlines
Wed, Aug 26 - Wed, Sep 2
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$215 Roundtrip, found 6 days ago
$215
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Aug 26 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Wed, Sep 2, priced at $215 found 6 days ago
Delta
Mon, Sep 28 - Fri, Oct 16
TPA
Tampa Intl.
BDL
Bradley Intl.
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Delta flight, departing Mon, Sep 28 from Tampa Intl. to Bradley Intl., returning Fri, Oct 16, priced at $217 found 11 hours ago
United
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$222 Roundtrip, found 15 hours ago
$222
Roundtrip
found 15 hours ago
Select United flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $222 found 15 hours ago
American Airlines
Wed, Sep 2 - Wed, Sep 9
TPA
Tampa Intl.
BDL
Bradley Intl.
$222 Roundtrip, found 15 hours ago
$222
Roundtrip
found 15 hours ago
Select American Airlines flight, departing Wed, Sep 2 from Tampa Intl. to Bradley Intl., returning Wed, Sep 9, priced at $222 found 15 hours ago
Frontier Airlines
Tue, Jul 21 - Sat, Aug 8
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$262 Roundtrip, found 2 days ago
$262
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Jul 21 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Aug 8, priced at $262 found 2 days ago
Bargain Flight
Sat, Sep 5 - Wed, Sep 9
PHX
Sky Harbor Intl.
BDL
Bradley Intl.
$316 Roundtrip, found 1 day ago
$316
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Sat, Sep 5 from Sky Harbor Intl. to Bradley Intl., returning Wed, Sep 9, priced at $316 found 1 day ago
Delta
Tue, Aug 18 - Sat, Sep 5
SFO
San Francisco Intl.
BDL
Bradley Intl.
$324 Roundtrip, found 13 hours ago
$324
Roundtrip
found 13 hours ago
Select Delta flight, departing Tue, Aug 18 from San Francisco Intl. to Bradley Intl., returning Sat, Sep 5, priced at $324 found 13 hours ago
Alaska Airlines
Wed, Sep 9 - Sat, Sep 19
SFO
San Francisco Intl.
BDL
Bradley Intl.
$664 Roundtrip, found 23 hours ago
$664
Roundtrip
found 23 hours ago
Select Alaska Airlines flight, departing Wed, Sep 9 from San Francisco Intl. to Bradley Intl., returning Sat, Sep 19, priced at $664 found 23 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 August, 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 15 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 $159, 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 $159 right now, why wait?

Windsor Flight Information
Destination airport
Bradley Intl.
Destination airport IATA code
BDL
Roundtrip price
$158

Last Minute Hotel Deals in 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 ...
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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 ...
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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 ...
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HYATT house Hartford North/Windsor
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! (1,437 reviews)
"Terribly dirty"

Reviewed on Jul 20, 2026

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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 ...
8.8/10 Excellent! (1,375 reviews)
"Good service and excellent hotel"

Reviewed on Jul 19, 2026

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Holiday Inn Express Southington by IHG
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 ...
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MGM Springfield
La Quinta Inn & Suites by Wyndham Springfield MA

La Quinta Inn & Suites by Wyndham Springfield MA

3 out of 5
100 Congress Street Springfield MA
Book a stay at this family-friendly hotel in Springfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
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La Quinta Inn & Suites by Wyndham Springfield MA
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd Hartford CT
Stay at this hotel in Hartford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular ...
7.8/10 Good! (1,094 reviews)
"The room was clean, but the hallway and stairwells were showing their age. The stairwells also smelled bad."

Reviewed on Jul 19, 2026

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Best Western Hartford Hotel & Suites
See all 761 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, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (1,000 reviews)
"The room was clean, I loved that there was laundry machines available for guests to use. Ice machines worked and was so handy."

Reviewed on Jul 12, 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. ...
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 ...
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 ...
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 ...
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. ...
Get rates
Residence Inn by Marriott Hartford/Windsor
See all 761 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.