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$377+ Cheap flights from Evansville (EVV) to Massachusetts

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
EVV — BOS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheap flight deals from Evansville to Massachusetts

Keep the following information in mind while searching for Evansville to Massachusetts flight deals. Data was last updated October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$377
(American Airlines)

Popular in

December

Cheapest in

June

Average price

$484
Provider with most accurate pricing for Evansville Dress Regional-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Evansville Dress Regional-Boston Logan Intl flights.
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From Evansville Dress Regional to Massachusetts
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Highest demand for flights based on searches. 7% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/30. 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.
Wed 12/314:51 pmEVV - BOS
1 stop5h 29mAmerican Airlines
Mon 1/510:44 amBOS - EVV
1 stop6h 37mAmerican Airlines
Deal found 10/30$377
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/275:10 amEVV - BOS
1 stop5h 05mAmerican Airlines
Thu 12/45:25 amBOS - EVV
1 stop6h 14mAmerican Airlines
Deal found 10/28$397
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/143:27 pmEVV - BOS
2 stops16h 39mMultiple Airlines
Sun 12/2112:22 pmBOS - EVV
1 stop24h 20mMultiple Airlines
Deal found 10/29$410
This American Airlines deal was found by Cheapflights users on 10/29. 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 12/1412:54 pmEVV - BOS
1 stop6h 59mAmerican Airlines
Sun 12/214:36 pmBOS - EVV
1 stop8h 01mAmerican Airlines
Deal found 10/29$413
This Delta deal was found by Cheapflights users on 10/29. 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 11/12:00 pmEVV - BOS
1 stop6h 15mDelta
Tue 11/46:50 amBOS - EVV
1 stop6h 53mDelta
Deal found 10/29$435
This Delta deal was found by Cheapflights users on 10/30. 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.
Fri 11/145:55 pmEVV - BOS
1 stop6h 35mDelta
Tue 11/185:05 pmBOS - EVV
1 stop6h 03mDelta
Deal found 10/30$480
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/711:50 amEVV - BOS
1 stop4h 45mAmerican Airlines
Sun 11/97:13 pmBOS - EVV
1 stop5h 41mAmerican Airlines
Deal found 10/29$525
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 10/315:35 pmEVV - BDL
1 stop19h 09mBreeze Airways
Sun 11/212:55 pmBDL - EVV
2 stops29h 00mBreeze Airways
Deal found 10/29$539
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/135:10 amEVV - BOS
1 stop4h 56mAmerican Airlines
Sun 11/165:18 pmBOS - EVV
1 stop7h 41mAmerican Airlines
Deal found 10/28$595
This Delta deal was found by Cheapflights users on 10/28. 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.
Thu 11/135:55 pmEVV - BOS
1 stop6h 35mDelta
Sun 11/169:59 pmBOS - EVV
2 stops12h 31mDelta
Deal found 10/28$664
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 10/315:35 pmEVV - BDL
1 stop19h 09mMultiple Airlines
Sun 11/21:36 pmBDL - EVV
1 stop28h 19mMultiple Airlines
Deal found 10/29$664
This Delta deal was found by Cheapflights users on 10/28. 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.
Fri 10/3112:00 pmEVV - BDL
1 stop5h 35mDelta
Sat 11/16:00 amBDL - EVV
1 stop4h 40mDelta
Deal found 10/28$687

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 October 30, 2025.
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

Wed 12/31

11:07 am-4:43 pm

1 stop4h 36m

Boston Logan Intl

Sun 1/4

6:51 pm-11:48 pm

1 stop5h 57m

$377

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Wed 12/31

4:51 pm-11:20 pm

1 stop5h 29m

Boston Logan Intl

Mon 1/5

10:44 am-4:21 pm

1 stop6h 37m

$377

EvansvilleHartford

EVV - BDL

EVVBDL

Evansville Dress Regional

Fri 2/13

5:45 pm-11:47 pm

1 stop5h 02m

Hartford Bradley Intl

Tue 2/17

5:05 pm-10:05 pm

1 stop6h 00m

$397

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Thu 11/27

5:10 am-1:15 pm

1 stop7h 05m

Boston Logan Intl

Thu 12/4

5:23 pm-11:58 pm

1 stop7h 35m

$397

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sun 12/14

3:27 pm-9:06 am

2 stops16h 39m

Boston Logan Intl

Sun 12/21

12:22 pm-11:42 am

1 stop24h 20m

$410

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sun 12/14

12:54 pm-8:53 pm

1 stop6h 59m

Boston Logan Intl

Sun 12/21

4:36 pm-11:37 pm

1 stop8h 01m

$413

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Sun 2/1

5:59 pm-1:04 am

1 stop6h 05m

Boston Logan Intl

Sun 2/22

5:30 pm-10:05 pm

1 stop5h 35m

$415

EvansvilleBoston

EVV - BOS

EVVBOS

Evansville Dress Regional

Fri 11/14

5:55 pm-1:30 am

1 stop6h 35m

Boston Logan Intl

Tue 11/18

5:05 pm-10:08 pm

1 stop6h 03m

$480

EvansvilleHartford

EVV - BDL

EVVBDL

Evansville Dress Regional

Fri 2/13

7:05 am-6:51 pm

2 stops10h 46m

Hartford Bradley Intl

Tue 2/17

12:01 pm-10:56 pm

2 stops11h 55m

$573

EvansvilleHartford

EVV - BDL

EVVBDL

Evansville Dress Regional

Tue 3/31

4:56 pm-12:22 am

1 stop6h 26m

Hartford Bradley Intl

Wed 4/1

6:05 am-10:10 am

1 stop5h 05m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 13 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, January is the cheapest month in which you can book a flight from Evansville to Massachusetts (average of $196). Flying from Evansville to Massachusetts in July 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 October 30, 2025.
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
11,034 reviews

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,034 reviews
American Airlines
7.2
Good
11,034 reviews

Food

6.4

Boarding

7.5

Comfort

7.2

Overall

7.2

Entertainment

6.9

Crew

8.0

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 36m. 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, January is the cheapest month in which you can book a flight from Evansville to Massachusetts (average of $196). Flying from Evansville to Massachusetts in July 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$366Average$483FlexibilityNo cancel feeOn-time71%

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