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Cheap flights from Indiana to Massachusetts from $48

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Indiana to Massachusetts departing on 9/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Indiana to Massachusetts

Cheap round-trip flights

Southwest Logo
5:40 pm - 9:00 pmMDW-BOS
2h 20mnonstop
Southwest Logo
8:20 pm - 9:55 pmBOS-MDW
2h 35mnonstop
$95Southwest
Find Deal
Sat, Sep 6 - Mon, Sep 8
Southwest Logo
9:20 pm - 12:40 amMDW-BOS
2h 20mnonstop
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
$100Southwest
Find Deal
Thu, Oct 30 - Tue, Nov 4
Southwest Logo
6:25 am - 3:25 pmMDW-BOS
8h 00m1 stop
Southwest Logo
8:20 pm - 9:55 pmBOS-MDW
2h 35mnonstop
$104Southwest
Find Deal
Wed, Sep 3 - Mon, Sep 8
American Airlines Logo
8:25 pm - 11:53 pmORD-BOS
2h 28mnonstop
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
$128American Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
American Airlines Logo
8:25 pm - 11:53 pmORD-BOS
2h 28mnonstop
American Airlines Logo
5:00 am - 6:51 amBOS-ORD
2h 51mnonstop
$129American Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
Delta Logo
6:00 pm - 9:38 pmORD-BOS
2h 38mnonstop
Delta Logo
7:55 pm - 9:56 pmBOS-ORD
3h 01mnonstop
$137Delta
Find Deal
Fri, Sep 5 - Tue, Sep 9
Delta Logo
7:00 am - 10:29 amORD-BOS
2h 29mnonstop
Delta Logo
5:00 pm - 7:11 pmBOS-ORD
3h 11mnonstop
$157Delta
Find Deal
Sat, Aug 23 - Sat, Aug 30
United Airlines Logo
6:30 am - 9:56 amORD-BOS
2h 26mnonstop
United Airlines Logo
6:10 am - 8:05 amBOS-ORD
2h 55mnonstop
$158United Airlines
Find Deal
Sun, Aug 31 - Sun, Sep 7
United Airlines Logo
11:40 am - 5:34 pmORD-BOS
4h 54m1 stop
United Airlines Logo
6:10 am - 8:05 amBOS-ORD
2h 55mnonstop
$167United Airlines
Find Deal
Tue, Sep 2 - Sun, Sep 7
Allegiant Air Logo
6:30 am - 8:10 amCVG-BOS
25h 40m2 stops
Allegiant Air Logo
11:36 am - 11:16 pmBOS-CVG
11h 40m1 stop
$272Allegiant Air
Find Deal
Sun, Aug 24 - Thu, Aug 28

Delta flights from Indiana to Massachusetts

Our best Delta deals on Indiana to Massachusetts flight tickets
Delta
Sep 5
ORD6:00 pmChicago O'Hare Intl
2h 38m
BOS9:38 pmBoston Logan Intl
Sep 9
BOS7:55 pmBoston Logan Intl
3h 01m
ORD9:56 pmChicago O'Hare Intl
$137
Find similar
Delta
Aug 23
ORD7:00 amChicago O'Hare Intl
2h 29m
BOS10:29 amBoston Logan Intl
Aug 30
BOS5:00 pmBoston Logan Intl
3h 11m
ORD7:11 pmChicago O'Hare Intl
$157
Find similar
Delta
Aug 15
ORD7:00 amChicago O'Hare Intl
2h 29m
BOS10:29 amBoston Logan Intl
Aug 21
BOS7:55 pmBoston Logan Intl
2h 59m
ORD9:54 pmChicago O'Hare Intl
$178
Find similar

United Airlines flights from Indiana to Massachusetts

Our best United Airlines deals on Indiana to Massachusetts flight tickets
United Airlines
Aug 16
ORD7:45 pmChicago O'Hare Intl
2h 27m
BOS11:12 pmBoston Logan Intl
Aug 23
BOS6:09 amBoston Logan Intl
2h 56m
ORD8:05 amChicago O'Hare Intl
$150
Find similar
United Airlines
Aug 31
ORD6:30 amChicago O'Hare Intl
2h 26m
BOS9:56 amBoston Logan Intl
Sep 7
BOS6:10 amBoston Logan Intl
2h 55m
ORD8:05 amChicago O'Hare Intl
$158
Find similar
United Airlines
Sep 2
ORD11:40 amChicago O'Hare Intl
4h 54m
1 stop
BOS5:34 pmBoston Logan Intl
Sep 7
BOS6:10 amBoston Logan Intl
2h 55m
ORD8:05 amChicago O'Hare Intl
$167
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Indiana 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, momondo users made 832,500 searches. Data last updated August 4, 2025.
Use the filters below to find and compare flights from Indiana to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 9/6

5:40 pm-9:00 pm

Nonstop2h 20m

Boston Logan Intl

Mon 9/8

8:20 pm-9:55 pm

Nonstop2h 35m

$95

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 10/30

9:20 pm-12:40 am

Nonstop2h 20m

Boston Logan Intl

Tue 11/4

5:35 pm-9:05 pm

1 stop4h 30m

$100

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 9/3

6:25 am-3:25 pm

1 stop8h 00m

Boston Logan Intl

Mon 9/8

8:20 pm-9:55 pm

Nonstop2h 35m

$104

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

8:25 pm-11:53 pm

Nonstop2h 28m

Boston Logan Intl

Sun 9/7

5:00 am-6:51 am

Nonstop2h 51m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

8:25 pm-11:53 pm

Nonstop2h 28m

Boston Logan Intl

Sun 9/7

5:00 am-6:51 am

Nonstop2h 51m

$129

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/5

6:00 pm-9:38 pm

Nonstop2h 38m

Boston Logan Intl

Tue 9/9

7:55 pm-9:56 pm

Nonstop3h 01m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/23

7:00 am-10:29 am

Nonstop2h 29m

Boston Logan Intl

Sat 8/30

5:00 pm-7:11 pm

Nonstop3h 11m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 8/31

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Sun 9/7

6:10 am-8:05 am

Nonstop2h 55m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 9/2

11:40 am-5:34 pm

1 stop4h 54m

Boston Logan Intl

Sun 9/7

6:10 am-8:05 am

Nonstop2h 55m

$167

CincinnatiBoston

CVG - BOS

CVGBOS

Cincinnati Cinci./N. Kentucky

Sun 8/24

6:30 am-8:10 am

2 stops25h 40m

Boston Logan Intl

Thu 8/28

11:36 am-11:16 pm

1 stop11h 40m

$272

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Massachusetts from

How to get the cheapest flight ticket from Indiana to Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Massachusetts?

In general, June is the cheapest month to fly from Indiana to Massachusetts. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $342. If you aren’t able to travel to Massachusetts during the month of June, then flying in August is also cheap. Prices for this month can be found on momondo for an average of $357.

What is the cheapest day to depart on your flight to Massachusetts?

According to our data, Thursday is the cheapest day to fly to Massachusetts from Indiana. The lowest ticket price found for a Thursday departure recently was $475. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Monday is the most expensive day to depart from Indiana because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $771.

What is the cheapest time of day to depart on your flight to Massachusetts?

Our data shows that the cheapest Indiana to Massachusetts flights are usually those with departure times in the morning. Our users have found flights to Massachusetts in the morning for as low as $476. If you have a flexible travel schedule, then try to avoid flying at noon when prices are $880 on average. Flights to Massachusetts from Indiana at noon are generally more expensive because this time of day is more convenient for travelers’ schedules.

What is the cheapest Indiana to Massachusetts flight route?

Fly from Indianapolis to Boston Logan Intl for the best Indiana - Massachusetts flight prices

How far in advance should I book a flight to Massachusetts?

You are more likely to see cheaper flights to Massachusetts from Indiana when booking weeks ahead of your departure date. In general, you can expect to find flights to Massachusetts for around $403 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Massachusetts from Indiana for as low as $351 on momondo.

What cabin class options are available on Indiana to Massachusetts flights?

There are 4 cabin classes available to choose from on Indiana to Massachusetts flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Indiana to Massachusetts flights?

You could potentially save up to 30% on your flight if you consider stops on a Indiana to Massachusetts flight.

  • When did momondo last update prices for flights from Indiana to Massachusetts?

    Prices for flights from Indiana to Massachusetts are updated daily.

  • How many operators does momondo search for flights from Indiana to Massachusetts?

  • How old do you have to be to fly from Indiana to Massachusetts?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Indiana to Massachusetts.

  • What documentation or ID do you need to fly to Massachusetts?

    The necessary travel and health documents for your Massachusetts trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Indiana to Massachusetts?

Best airlines flying from Indiana to Massachusetts

Compare and see reviews for airlines that fly from Indiana to Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
Allegiant AirPriceFrom $70Free CancellationRating
7.2
702 reviews
Search Allegiant Air flights
FrontierPriceFrom $112Free CancellationRating
5.8
3,231 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $126Free CancellationRating
6.3
8,053 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $191Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $207Free CancellationRating
8.0
7,986 reviews
Search Delta flights
United AirlinesPriceFrom $243Free CancellationRating
7.4
8,909 reviews
Search United Airlines flights
SouthwestPriceFrom $332Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Indiana to Massachusetts?

It is quick and easy to find Indiana to Massachusetts flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Massachusetts that suits you.

Can I find flights from Indiana to Massachusetts with flexible booking policies on momondo?

All flight searches from Indiana to Massachusetts on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Indiana to Massachusetts?

Once all potential Indiana to Massachusetts flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Indiana to Massachusetts right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Indiana to Massachusetts flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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