Cheap Flights to Simsbury from $56

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How Much Does it Cost To Fly To Simsbury?

The cheapest prices found with in the last 7 days for return flights were $107 and $56 for one-way flights to Simsbury for the period specified. Prices and availability are subject to change. Additional terms apply

OriginDestinationTravel DatesFlights From*
MCOWindsor LocksMay 30 to June 1$141
TPAWindsor LocksAugust 19 to August 24$173
SJUWindsor LocksMay 27 to May 31$192
FLLWindsor LocksJuly 1 to September 2$203
ORDWindsor LocksJune 3 to June 6$218
ATLWindsor LocksAugust 7 to August 10$220
DCAWindsor LocksJune 4 to June 7$225
DENWindsor LocksJune 11 to June 15$256
LAXWindsor LocksJune 3 to September 26$272
CLTWindsor LocksJune 13 to June 20$302
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOWindsor LocksMay 16 to June 15$269
SJUWindsor LocksMay 16 to May 18$351
TPAWindsor LocksMay 16 to May 18$409
CLTWindsor LocksMay 16 to May 18$450
DCAWindsor LocksMay 16 to May 17$458
FLLWindsor LocksMay 17 to May 19$464
DENWindsor LocksMay 17 to May 24$468
ATLWindsor LocksMay 17 to May 21$601
LAXWindsor LocksMay 17 to May 20$651
ORDWindsor LocksMay 16 to May 18$830
*Prices include taxes and fees

Simsbury Flight Information

Traveling to
Simsbury
Lowest Price
$107
Number of Airlines Serving
Airlines Serving
Breeze Airways
Number of Daily Flights
Airlines with Direct Flights

Find The Perfect Hotel For After Your Flight

Amazing Simsbury Accommodation Deals

Iron Horse Inn

Iron Horse Inn

2 out of 5
969 Hopmeadow Street Simsbury CT
Stay at this hotel in Simsbury. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Performing Arts Center at Simsbury Meadows and Rosedale ...
7.2/10 Good! (140 reviews)
Great

Reviewed on Nov 7, 2021

Opens in a new windowIron Horse Inn
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.

Our Top Simsbury with Airport Shuttles

Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
$186 nightly
The price is $214 total per night from May 19 to May 20
$214 total
May 19 - May 20
Total with taxes and fees
Book a stay at this business-friendly B&B in Simsbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
A fun, cute Bed and Breakfast in an adorable town. The Deluxe Suite was well worth the price. The in-room Jacuzzi was amazing.

Reviewed on May 3, 2026

Opens in a new windowSimsbury 1820 House
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.

Luxury Hotels in Simsbury

Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
$186 nightly
The price is $214 total per night from May 19 to May 20
$214 total
May 19 - May 20
Total with taxes and fees
Book a stay at this business-friendly B&B in Simsbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
A fun, cute Bed and Breakfast in an adorable town. The Deluxe Suite was well worth the price. The in-room Jacuzzi was amazing.

Reviewed on May 3, 2026

Opens in a new windowSimsbury 1820 House
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.

Family Friendly Hotels in Simsbury

Simsbury 1820 House

Simsbury 1820 House

4 out of 5
731 Hopmeadow St Simsbury CT
$186 nightly
The price is $214 total per night from May 19 to May 20
$214 total
May 19 - May 20
Total with taxes and fees
Book a stay at this business-friendly B&B in Simsbury. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (1,000 reviews)
A fun, cute Bed and Breakfast in an adorable town. The Deluxe Suite was well worth the price. The in-room Jacuzzi was amazing.

Reviewed on May 3, 2026

Opens in a new windowSimsbury 1820 House
Iron Horse Inn

Iron Horse Inn

2 out of 5
969 Hopmeadow Street Simsbury CT
Stay at this hotel in Simsbury. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Performing Arts Center at Simsbury Meadows and Rosedale ...
7.2/10 Good! (140 reviews)
Great

Reviewed on Nov 7, 2021

Opens in a new windowIron Horse Inn
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.

Best Simsbury Flight and Hotel Packages

Simsbury flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Cromwell/Middletown
Inn at Middletown
Graduate by Hilton Storrs
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Plane Tickets To Simsbury

Although you may try and resist the urge, you know that when the travel bug comes, there is only one way to get rid of it. Thankfully, Travelocity is here to help nip that travel bug in the bud with great deals on flights to Simsbury. Browse through our inventory to explore a wide range of cheap flights to Simsbury to solidify your next big trip out of town. Whether you are heading out on a business trip, exploring a place you have never been for pleasure or are bringing the family on the annual vacation, we have the perfect getaway waiting for you. In no time, you will be day dreaming of your plane landing in Simsbury as you anxiously await to exit the plane and explore what Simsbury has to offer. Considering all the amazing local food and culture in Simsbury, we won't hold this against you.

When you are ready to embark on your next big adventure, Travelocity will be right here waiting to open the doors to the garden so that you can go and smell the roses. When you decide to book and travel is entirely up to you, but don't wait too long because we have some of the best deals on the web and they won't last long. Take time to go through our huge selection of cheap flights to Simsbury to find the best deals that fit into your budget. If browsing on your phone while your boss isn't looking is more your thing (we promise we won't tell), consider checking out Travelocity's mobile app which allows you to take advantage of all our flights to Simsbury without having to compromise your work computer's search history. If you are looking to save even more, you can easily save up to $537 when you bundle one of our cheap flights to Simsbury with one of our hotels. So why are you waiting around? There is no better time than now to start booking that next trip. Start your search now to book one of our flights to Simsbury today!

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.