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$252+ Cheap flights from Evansville (EVV) to Massachusetts

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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — BOS
Apr 29 — May 61
Wed 4/29
Wed 5/6
1 adult, Economy
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Cheap flight deals from Evansville to Massachusetts

Cheapest flights from Evansville to Massachusetts
Explore the most affordable flight options available from Evansville to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 30, 2026.

This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:23 pm
EVV
-
BOS
1 stop5h 02m
American Airlines
Tue 5/56:48 pm
BOS
-
EVV
1 stop6h 06m
American Airlines
Deal found 3/25$379
This American Airlines deal was found by Cheapflights users on 3/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:23 pm
EVV
-
BOS
1 stop5h 02m
American Airlines
Mon 5/46:53 pm
BOS
-
EVV
1 stop5h 35m
American Airlines
Deal found 3/25$417
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 6/158:40 pm
EVV
-
BOS
1 stop21h 35m
Multiple Airlines
Thu 6/259:12 am
BOS
-
EVV
2 stops35h 33m
Multiple Airlines
Deal found 3/27$423
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:33 am
EVV
-
BOS
1 stop6h 53m
American Airlines
Sun 4/265:40 pm
BOS
-
EVV
1 stop6h 48m
American Airlines
Deal found 3/28$487
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:23 pm
EVV
-
BOS
1 stop5h 02m
American Airlines
Sun 4/265:40 pm
BOS
-
EVV
1 stop6h 48m
American Airlines
Deal found 3/27$503
This Delta deal was found by Cheapflights users on 3/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/105:59 pm
EVV
-
BOS
1 stop6h 14m
Delta
Tue 4/1411:15 am
BOS
-
EVV
1 stop7h 03m
Delta
Deal found 3/26$533
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:58 pm
EVV
-
BDL
1 stop5h 01m
Delta
Tue 4/286:00 am
BDL
-
EVV
1 stop7h 51m
Delta
Deal found 3/30$536
This Kiwi.com deal was found by Cheapflights users on 3/26. 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 4/247:46 pm
EVV
-
BOS
2 stops26h 39m
Multiple Airlines
Mon 4/2710:08 am
BOS
-
EVV
1 stop9h 58m
Multiple Airlines
Deal found 3/26$538
This Delta deal was found by Cheapflights users on 3/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/276:00 am
EVV
-
BOS
1 stop7h 38m
Delta
Sun 3/295:35 am
BOS
-
EVV
1 stop6h 04m
Delta
Deal found 3/25$565
This Kiwi.com deal was found by Cheapflights users on 3/28. 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 4/128:42 am
EVV
-
BOS
2 stops23h 27m
Multiple Airlines
Thu 4/163:27 pm
BOS
-
EVV
1 stop28h 39m
Multiple Airlines
Deal found 3/28$572
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:56 pm
EVV
-
BDL
1 stop4h 29m
American Airlines
Tue 4/2812:02 pm
BDL
-
EVV
2 stops11h 56m
American Airlines
Deal found 3/30$830

Find flight deals from Evansville to Massachusetts

Keep the following information in mind while searching for Evansville to Massachusetts flight deals. Data was last updated March 30, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$379
(American Airlines)

One-way from

$252
(Kiwi.com)

Popular in

October

Cheapest in

September
Provider with most accurate pricing for Evansville Dress Regional-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Evansville Dress Regional-Boston Logan Intl flights.
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From Evansville Dress Regional to Massachusetts
Search Deals
One-way flight from Evansville Dress Regional to Massachusetts
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High demand for flights, 5% potential price rise
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Evansville to Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 30, 2026.
Use the filters below to find and compare flights from Evansville to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Tue 9/8

6:31 am-12:34 pm

1 stop5h 03m

Boston Logan Intl

Thu 9/17

5:53 pm-11:21 pm

1 stop6h 28m

$417

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Fri 4/10

5:59 pm-1:13 am

1 stop6h 14m

Boston Logan Intl

Tue 4/14

11:15 am-5:18 pm

1 stop7h 03m

$533

EvansvilleHartford

EVV - BDL

EVVBDL

Evansville Dress Regional

Sun 4/26

5:58 pm-11:59 pm

1 stop5h 01m

Hartford Bradley Intl

Tue 4/28

6:00 am-12:51 pm

1 stop7h 51m

$536

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Fri 4/10

6:23 pm-12:25 am

1 stop5h 02m

Boston Logan Intl

Tue 4/14

5:30 pm-11:54 pm

2 stops7h 24m

$749

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sat 5/2

6:23 pm-12:25 am

1 stop5h 02m

Boston Logan Intl

Mon 5/4

5:30 pm-11:54 pm

2 stops7h 24m

$764

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Wed 4/22

5:10 am-2:19 pm

2 stops8h 09m

Boston Logan Intl

Sun 4/26

4:34 pm-11:54 pm

1 stop8h 20m

$773

EvansvilleHartford

EVV - BDL

EVVBDL

Evansville Dress Regional

Sun 4/26

6:56 pm-12:25 am

1 stop4h 29m

Hartford Bradley Intl

Tue 4/28

12:02 pm-10:58 pm

2 stops11h 56m

$830

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Mon 6/15

6:22 am-3:20 pm

1 stop7h 58m

Boston Logan Intl

Thu 6/25

10:20 am-5:21 pm

1 stop8h 01m

$849

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sat 5/2

6:00 am-3:28 pm

2 stops8h 28m

Boston Logan Intl

Mon 5/4

1:30 pm-10:42 pm

2 stops10h 12m

$1,324

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sat 5/2

6:00 am-3:28 pm

2 stops8h 28m

Boston Logan Intl

Wed 5/6

6:00 am-5:18 pm

2 stops12h 18m

$1,423

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 17 resultsSorted by cheapest first
1
2

Best time to book a flight from Evansville to Massachusetts

Have a flexible travel schedule? Discover the best time to fly to Massachusetts from Evansville 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.

Cheapflights Insights

Everything you need to know about your flight from Evansville to Massachusetts

What is the cheapest month to book a flight from Evansville to Massachusetts?

Currently, October is the cheapest month in which you can book a flight from Evansville to Massachusetts (average of $197). Flying from Evansville to Massachusetts in January is currently the most expensive (average of $304). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

How much does it cost to fly round-trip from Evansville to Massachusetts?

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Massachusetts. Reviews last updated March 30, 2026.
Peruse reviews from past customers who have flown with American Airlines from Evansville to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.1
Good
11,531 reviews

Comfort

7.2

Crew

7.9

Entertainment

6.9

Food

6.4

Boarding

7.5

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes
American Airlines
7.1
Good
11,531 reviews
American Airlines
7.1
Good
11,531 reviews

Comfort

7.2

Crew

7.9

Entertainment

6.9

Food

6.4

Boarding

7.5

Overall

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Mar 2026

MIA - SFO

Horrible. When they power flights for other airlines there is nothing they can do to change or accommodate any changes

Related info for your journey

Find useful and relevant information for your journey from Evansville to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Evansville to Massachusetts?

    Most people fly from Evansville Dress Regional (EVV) if they book a flight from Evansville to Massachusetts. Evansville Dress Regional is conveniently located just 4.4 mi from Evansville’s city center.

  • How long is the flight from Evansville to Massachusetts?

    There are many flights that can get you from Evansville to Massachusetts in 5h 03m. Fly via American Airlines or Delta to get the fastest option. There are 920 mi between Evansville and Massachusetts. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Evansville to Massachusetts that include hotel bookings?

    Yes. In addition to deals on Evansville to Massachusetts flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Evansville to Massachusetts?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Evansville to Massachusetts.

  • Can I find deals for business class flights from Evansville to Massachusetts?

    Yes. Cheapflights offers flight deals from Evansville to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Evansville to Massachusetts?

    Currently, October is the cheapest month in which you can book a flight from Evansville to Massachusetts (average of $197). Flying from Evansville to Massachusetts in January is currently the most expensive (average of $304). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Evansville to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top airline flying from Evansville to Massachusetts

Discover the top airline that operate flights from Evansville to Massachusetts. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 30, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$338Average$445FlexibilityNo cancel feeOn-time71%

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