Cheap Flights to Simsbury from $29

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

How Much Does it Cost To Fly To Simsbury?

The cheapest prices found with in the last 7 days for return flights were $56 and $29 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 7 to May 9$56
ATLWindsor LocksFebruary 19 to February 26$93
TPAWindsor LocksMarch 6 to March 9$129
SJUWindsor LocksFebruary 26 to March 1$156
FLLWindsor LocksApril 2 to April 15$157
CLTWindsor LocksMay 4 to May 7$160
ORDWindsor LocksApril 23 to April 27$161
DENWindsor LocksFebruary 24 to February 28$181
DCAWindsor LocksMarch 19 to March 22$194
LAXWindsor LocksMay 8 to May 14$229
*Prices include taxes and fees
OriginDestinationTravel DatesFlights From*
MCOWindsor LocksFebruary 14 to February 19$104
SJUWindsor LocksFebruary 14 to February 21$156
ATLWindsor LocksFebruary 14 to February 15$222
FLLWindsor LocksFebruary 15 to February 17$228
TPAWindsor LocksFebruary 14 to February 22$254
DCAWindsor LocksFebruary 13 to February 15$284
ORDWindsor LocksFebruary 15 to February 22$313
DENWindsor LocksFebruary 14 to February 21$315
LAXWindsor LocksFebruary 14 to March 3$319
CLTWindsor LocksFebruary 13 to February 16$429
*Prices include taxes and fees

Simsbury Flight Information

Traveling to
Simsbury
Lowest Price
$56
Number of Airlines Serving
Airlines Serving
Frontier Airlines
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 ...
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
$174 nightly
The price is $200 total per night from Feb 9 to Feb 10
$200 total
Feb 9 - Feb 10
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! (1,002 reviews)
Gorgeous.

Reviewed on Feb 6, 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
$174 nightly
The price is $200 total per night from Feb 9 to Feb 10
$200 total
Feb 9 - Feb 10
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! (1,002 reviews)
Gorgeous.

Reviewed on Feb 6, 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
$174 nightly
The price is $200 total per night from Feb 9 to Feb 10
$200 total
Feb 9 - Feb 10
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! (1,002 reviews)
Gorgeous.

Reviewed on Feb 6, 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 ...
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.
Motel 6 Enfield, CT - Hartford
Hilton Garden Inn Hartford South/Glastonbury
Holiday Inn Express Southington by IHG
Don't see what you're looking for?
See all available trips from Orlando to Simsbury
View all trips

Need a Car For After Your Flight?

Lowest prices found within the past 5 days. Prices and availability subject to change. Additional terms may apply.

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!

Explore More Ways to Travel with Travelocity

*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.