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$185+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — BOS
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 4/207:46 pm
EVV
-
BOS
1 stop21h 49m
Multiple Airlines
Tue 5/511:16 am
BOS
-
EVV
1 stop29h 33m
Multiple Airlines
Deal found 1/28$259
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 4/207:46 pm
EVV
-
BOS
1 stop21h 49m
Multiple Airlines
Mon 5/411:16 am
BOS
-
EVV
1 stop8h 50m
Multiple Airlines
Deal found 1/28$271
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:58 pm
EVV
-
BOS
1 stop6h 24m
Delta
Sat 5/212:45 pm
BOS
-
EVV
1 stop5h 33m
Delta
Deal found 1/28$339
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 4/247:46 pm
EVV
-
BOS
2 stops35h 11m
Multiple Airlines
Tue 5/511:16 am
BOS
-
EVV
1 stop29h 33m
Multiple Airlines
Deal found 1/28$341
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 3/277:46 pm
EVV
-
BOS
2 stops14h 27m
Multiple Airlines
Sun 3/294:23 pm
BOS
-
EVV
1 stop27h 43m
Multiple Airlines
Deal found 1/28$347
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Fri 4/247:46 pm
EVV
-
BOS
2 stops35h 11m
Multiple Airlines
Mon 5/411:16 am
BOS
-
EVV
1 stop8h 50m
Multiple Airlines
Deal found 1/28$352
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 4/207:46 pm
EVV
-
BOS
1 stop21h 49m
Multiple Airlines
Fri 5/111:16 am
BOS
-
EVV
1 stop8h 50m
Multiple Airlines
Deal found 1/28$360
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/185:58 pm
EVV
-
BOS
1 stop6h 24m
Delta
Thu 4/305:40 am
BOS
-
EVV
1 stop8h 11m
Delta
Deal found 1/28$377
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 4/193:22 pm
EVV
-
BOS
2 stops16h 47m
Multiple Airlines
Tue 5/511:16 am
BOS
-
EVV
1 stop29h 33m
Multiple Airlines
Deal found 1/28$393
This Delta deal was found by Cheapflights users on 1/26. 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.
Sat 4/115:59 pm
EVV
-
BDL
1 stop4h 56m
Delta
Wed 4/156:00 am
BDL
-
EVV
1 stop5h 31m
Delta
Deal found 1/26$397
This Delta deal was found by Cheapflights users on 1/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/65:59 pm
EVV
-
BDL
1 stop4h 57m
Delta
Sun 3/86:00 am
BDL
-
EVV
1 stop5h 39m
Delta
Deal found 1/27$407
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Fri 3/611:08 am
EVV
-
BDL
1 stop4h 25m
American Airlines
Sun 3/85:30 am
BDL
-
EVV
2 stops11h 19m
American Airlines
Deal found 1/27$600

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(Kiwi.com)

One-way from

$185
(Kiwi.com)

Popular in

January

Cheapest in

June

Average price

$610
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.
Search Deals
From Evansville Dress Regional to Massachusetts
Search Deals
One-way flight from Evansville Dress Regional to Massachusetts
Search Deals
Highest demand for flights based on searches. 10% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 January 29, 2026.
Use the filters below to find and compare flights from Evansville to Massachusetts that are best for you.

Fly from

Evansville

Fly to

Massachusetts

Route

Depart

Return

Price

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Mon 4/20

7:46 pm-6:35 pm

1 stop21h 49m

Boston Logan Intl

Tue 5/5

12:55 pm-3:49 pm

2 stops27h 54m

$302

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Mon 4/20

7:46 pm-3:14 pm

2 stops18h 28m

Boston Logan Intl

Mon 5/4

11:16 am-7:06 pm

1 stop8h 50m

$308

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Wed 4/22

5:58 pm-1:15 am

1 stop6h 17m

Boston Logan Intl

Tue 5/5

11:15 am-5:18 pm

1 stop7h 03m

$339

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Wed 4/22

5:58 pm-11:58 pm

1 stop5h 00m

Boston Logan Intl

Sat 5/2

12:45 pm-5:18 pm

1 stop5h 33m

$339

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Tue 4/21

5:58 pm-11:58 pm

1 stop5h 00m

Boston Logan Intl

Wed 4/29

6:50 am-12:51 pm

1 stop7h 01m

$339

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Fri 3/27

7:46 pm-9:54 am

1 stop13h 08m

Boston Logan Intl

Sun 3/29

4:23 pm-7:06 pm

1 stop27h 43m

$339

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sat 4/18

5:58 pm-11:58 pm

1 stop5h 00m

Boston Logan Intl

Tue 5/5

5:40 am-12:51 pm

1 stop8h 11m

$339

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Mon 4/20

7:46 pm-6:35 pm

1 stop21h 49m

Boston Logan Intl

Fri 5/1

11:16 am-7:06 pm

1 stop8h 50m

$360

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sun 4/19

5:58 pm-11:58 pm

1 stop5h 00m

Boston Logan Intl

Wed 4/29

5:40 am-12:51 pm

1 stop8h 11m

$377

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sat 4/18

5:58 pm-1:22 am

1 stop6h 24m

Boston Logan Intl

Thu 4/30

5:40 am-12:51 pm

1 stop8h 11m

$377

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 19 results
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, March is the cheapest month in which you can book a flight from Evansville to Massachusetts (average of $197). Flying from Evansville to Massachusetts in June is currently the most expensive (average of $275). 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.

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 January 29, 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
7.2
Good
11,205 reviews

Overall

7.2

Crew

8.0

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,205 reviews
American Airlines
7.2
Good
11,205 reviews

Overall

7.2

Crew

8.0

Comfort

7.2

Boarding

7.5

Entertainment

6.9

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

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 4h 25m. Fly via Delta or American Airlines to get the fastest option. There are 829 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, March is the cheapest month in which you can book a flight from Evansville to Massachusetts (average of $197). Flying from Evansville to Massachusetts in June is currently the most expensive (average of $275). 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$338Average$439FlexibilityNo cancel feeOn-time71%

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