HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Rutland

$72+ Cheap flights from Rutland

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/21. Fares are subject to change and may not be available on all flights or dates of travel.
RUT — RSW
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

What to know about flights from Rutland

Discover essential information about flights departing from Rutland, including flight schedules, destinations, airlines operating at the Rutland airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated February 16, 2026.

Cheapest airline

JetBlue

Good round-trip deal

$172 or less

Good one-way deal

$91 or less
On average, JetBlue currently has the cheapest one-way flight from Rutland (avg. price of $494).
Search Deals
Price to beat on a round-trip flight from Rutland.
Search Deals
Price to beat on a one-way flight from Rutland.
Search Deals

Find flights from Rutland

Cheapest flights from Rutland
Explore the most affordable flight options available from Rutland. Find the lowest fares based on data from user searches, with prices last updated on February 16, 2026.

This Mytrip deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/283:31 pm
RUT
-
BOS
Nonstop1h 20m
Cape Air
Wed 3/41:47 pm
BOS
-
RUT
Nonstop1h 20m
Cape Air
Deal found 2/12$147
This Booking.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:15 am
RUT
-
BOS
Nonstop1h 17m
Cape Air
Fri 3/61:47 pm
BOS
-
RUT
Nonstop1h 20m
Cape Air
Deal found 2/15$148
This Cape Air deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:15 am
RUT
-
BOS
Nonstop1h 17m
Cape Air
Tue 3/38:58 am
BOS
-
RUT
Nonstop1h 20m
Cape Air
Deal found 2/12$160
This Booking.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/711:19 am
RUT
-
BOS
Nonstop1h 17m
Cape Air
Mon 4/131:47 pm
BOS
-
RUT
Nonstop1h 20m
Cape Air
Deal found 2/13$178
This Cape Air deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cape Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3011:19 am
RUT
-
BOS
Nonstop1h 17m
Cape Air
Fri 5/158:58 am
BOS
-
RUT
Nonstop1h 20m
Cape Air
Deal found 2/12$200
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:15 am
RUT
-
MCO
1 stop12h 35m
Multiple Airlines
Fri 3/68:50 am
MCO
-
RUT
1 stop6h 17m
Multiple Airlines
Deal found 2/14$293
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/93:31 pm
RUT
-
MCO
1 stop24h 39m
Multiple Airlines
Thu 3/126:33 pm
MCO
-
RUT
1 stop15h 45m
Multiple Airlines
Deal found 2/13$300
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:15 am
RUT
-
MCO
1 stop12h 35m
Multiple Airlines
Thu 3/126:33 pm
MCO
-
RUT
1 stop15h 45m
Multiple Airlines
Deal found 2/13$307
This Priceline deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/83:31 pm
RUT
-
FLL
1 stop7h 26m
Multiple Airlines
Thu 3/126:00 am
FLL
-
RUT
1 stop9h 07m
Multiple Airlines
Deal found 2/15$314
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1511:19 am
RUT
-
RSW
1 stop7h 00m
Multiple Airlines
Wed 3/187:24 pm
RSW
-
RUT
1 stop19h 43m
Multiple Airlines
Deal found 2/12$317
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2011:19 am
RUT
-
FLL
1 stop21h 49m
Multiple Airlines
Sat 3/289:00 pm
FLL
-
RUT
1 stop18h 07m
Multiple Airlines
Deal found 2/13$328
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/93:31 pm
RUT
-
MCO
1 stop24h 39m
Multiple Airlines
Mon 3/169:37 pm
MCO
-
RUT
2 stops17h 30m
Multiple Airlines
Deal found 2/13$329

Find flights from Rutland within your budget

 
Find flights departing from Rutland that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on February 16, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Fort Myers

Route

Depart

Return

Price

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Sat 2/28

3:31 pm-4:51 pm

Nonstop1h 20m

Boston Logan Intl

Wed 3/4

1:47 pm-3:07 pm

Nonstop1h 20m

$147

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Mon 3/2

7:15 am-8:32 am

Nonstop1h 17m

Boston Logan Intl

Fri 3/6

1:47 pm-3:07 pm

Nonstop1h 20m

$148

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Tue 3/17

11:19 am-12:36 pm

Nonstop1h 17m

Boston Logan Intl

Tue 3/24

8:58 am-10:18 am

Nonstop1h 20m

$148

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Mon 3/2

7:15 am-8:32 am

Nonstop1h 17m

Boston Logan Intl

Tue 3/3

8:58 am-10:18 am

Nonstop1h 20m

$160

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Tue 3/3

7:15 am-8:32 am

Nonstop1h 17m

Boston Logan Intl

Sat 3/7

5:11 pm-6:31 pm

Nonstop1h 20m

$160

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Mon 3/2

7:15 am-8:32 am

Nonstop1h 17m

Boston Logan Intl

Wed 3/4

1:47 pm-3:07 pm

Nonstop1h 20m

$160

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Mon 3/2

7:15 am-8:32 am

Nonstop1h 17m

Boston Logan Intl

Mon 3/2

5:11 pm-6:31 pm

Nonstop1h 20m

$160

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Tue 4/7

11:19 am-12:36 pm

Nonstop1h 17m

Boston Logan Intl

Mon 4/13

1:47 pm-3:07 pm

Nonstop1h 20m

$178

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Thu 4/30

11:19 am-12:36 pm

Nonstop1h 17m

Boston Logan Intl

Fri 5/15

8:58 am-10:18 am

Nonstop1h 20m

$200

RutlandBoston

RUT - BOS

RUTBOS

Rutland

Mon 7/6

11:33 am-12:58 pm

Nonstop1h 25m

Boston Logan Intl

Wed 7/8

1:43 pm-3:11 pm

Nonstop1h 28m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/13

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Rutland

Have a flexible travel schedule? Discover the best time to fly from Rutland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Rutland

Get recent, data-driven insights about flights from Rutland including ideal travel times, pricing trends, and more.

What is the cheapest month to book a flight from Rutland?

Currently, November is the cheapest month in which you can book a flight from Rutland (average of $61). Flying from Rutland in March will prove the most costly (average of $154). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

What is the cheapest place to fly to from Rutland?

The cheapest city to fly to from Rutland is Boston Logan Intl, with prices starting at $73. Explore other affordable destinations below.

Boston Logan Intl
Boston Logan Intl
From $73

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Airports servicing Rutland

Fly out of one of these airports located in Rutland.
Flights from Albany
Flights from Lebanon
Flights from Hartford
Flights from Burlington

Related info for your journey

Access useful and relevant information related to your journey from Rutland. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated February 16, 2026.

  • What is the cheapest flight from Rutland to anywhere?

    Users have flown out of Rutland for as low as $73 to Boston (prices may vary depending on the airline and departure time). On average, users have booked flights for $248 to fly from Rutland.

  • What is the cheapest month to fly from Rutland?

    November is currently the cheapest month to fly from Rutland. At this moment in time March is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights