$50+ Cheap flights from Massachusetts to Indiana
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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — IND
Feb 14 — Feb 211
1 adult, Economy
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1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Massachusetts to Indiana
Keep the following information in mind while searching for Massachusetts to Indiana flight deals. Data was last updated January 15, 2026.
Most accurate provider | eDreams 3 stars |
|---|---|
Most trusted provider | eDreams 3 stars |
Round-trip from | $131 (Booking.com) |
One-way from | $50 (Mytrip) |
Popular in | October |
Cheapest in | June |
Average price | $447 |
Good round-trip deal | $378 or less |
Good one-way deal | $298 or less |
Find flight deals from Massachusetts to Indiana
Cheapest flights from Massachusetts to IndianaExplore the most affordable flight options available from Massachusetts to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.
Explore the most affordable flight options available from Massachusetts to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.
This Booking.com deal was found by Cheapflights users on 1/13. 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 2/36:00 am
BOS
- ORD
1 stop8h 58m
Multiple Airlines
Wed 2/410:48 am
ORD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 1/13![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/276:00 am
BOS
- MDW
1 stop13h 38m
Frontier
Mon 3/26:00 am
MDW
- BOS
1 stop18h 13m
Frontier
Deal found 1/15![Frontier logo]()
$132
This Priceline deal was found by Cheapflights users on 1/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/63:35 pm
BOS
- ORD
Nonstop3h 08m
Multiple Airlines
Sat 2/77:20 am
ORD
- BOS
1 stop8h 28m
Multiple Airlines
Deal found 1/13![Multiple Airlines logo]()
$132
This Kiwi.com deal was found by Cheapflights users on 1/13. 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 2/236:00 am
BOS
- MDW
1 stop14h 47m
Frontier
Mon 3/22:19 pm
MDW
- BOS
1 stop9h 54m
Frontier
Deal found 1/13![Frontier logo]()
$133
This Priceline deal was found by Cheapflights users on 1/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/93:35 pm
BOS
- ORD
Nonstop3h 08m
Multiple Airlines
Wed 2/116:02 pm
ORD
- BOS
1 stop6h 11m
Multiple Airlines
Deal found 1/13![Multiple Airlines logo]()
$133
This Expedia deal was found by Cheapflights users on 1/13. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/23:35 pm
BOS
- ORD
Nonstop3h 08m
Multiple Airlines
Wed 2/410:48 am
ORD
- BOS
1 stop11h 31m
Multiple Airlines
Deal found 1/13![Multiple Airlines logo]()
$134
This United Airlines deal was found by Cheapflights users on 1/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/226:00 am
BOS
- ORD
Nonstop3h 04m
United Airlines
Fri 1/237:30 am
ORD
- BOS
Nonstop2h 22m
United Airlines
Deal found 1/15![United Airlines logo]()
$135
This American Airlines deal was found by Cheapflights users on 1/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/227:00 am
BOS
- ORD
Nonstop3h 05m
American Airlines
Sun 1/257:00 am
ORD
- BOS
Nonstop2h 23m
American Airlines
Deal found 1/15![American Airlines logo]()
$136
This Southwest deal was found by Cheapflights users on 1/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/65:45 pm
BOS
- MDW
Nonstop2h 50m
Southwest
Sun 2/82:00 pm
MDW
- BOS
Nonstop2h 10m
Southwest
Deal found 1/13![Southwest logo]()
$137
This JetBlue deal was found by Cheapflights users on 1/15. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/53:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Sun 2/87:45 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 1/15![JetBlue logo]()
$137
This JetBlue deal was found by Cheapflights users on 1/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/213:35 pm
BOS
- ORD
Nonstop3h 08m
JetBlue
Fri 1/307:40 am
ORD
- BOS
Nonstop2h 25m
JetBlue
Deal found 1/13![JetBlue logo]()
$138
This American Airlines deal was found by Cheapflights users on 1/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/185:18 pm
BOS
- ORD
Nonstop3h 18m
American Airlines
Thu 1/227:00 am
ORD
- BOS
Nonstop2h 23m
American Airlines
Deal found 1/15![American Airlines logo]()
$139
Cheapflights Fare Finder
Customize your flight search to find flights from Massachusetts to Indiana 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 15, 2026.
Use the filters below to find and compare flights from Massachusetts to Indiana that are best for you.
Fly from
Massachusetts
Fly to
Indiana
Route
Depart
Return
Price
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 1/21
4:16 pm-6:16 pm
Nonstop3h 00m
Chicago O'Hare Intl
Fri 1/23
7:30 am-10:52 am
Nonstop2h 22m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sun 3/8
7:25 am-9:35 am
Nonstop3h 10m
Chicago O'Hare Intl
Tue 3/17
10:40 am-2:04 pm
Nonstop2h 24m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 1/24
4:49 pm-6:49 pm
Nonstop3h 00m
Chicago O'Hare Intl
Wed 1/28
11:05 am-2:30 pm
Nonstop2h 25m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Wed 1/28
9:30 am-11:34 am
Nonstop3h 04m
Chicago O'Hare Intl
Wed 1/28
6:05 pm-9:38 pm
Nonstop2h 33m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/29
10:30 am-12:34 pm
Nonstop3h 04m
Chicago O'Hare Intl
Sat 1/31
9:13 am-12:46 pm
Nonstop2h 33m
$135
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Sat 3/7
7:16 am-9:22 am
Nonstop3h 06m
Chicago O'Hare Intl
Sat 3/7
9:15 pm-12:36 am
Nonstop2h 21m
$135
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Fri 2/6
5:45 pm-7:35 pm
Nonstop2h 50m
Chicago Midway
Sun 2/8
2:00 pm-5:10 pm
Nonstop2h 10m
$137
BostonChicago
BOS - MDW
BOSMDW
Boston Logan Intl
Mon 2/23
5:20 am-7:10 am
Nonstop2h 50m
Chicago Midway
Fri 2/27
6:05 am-9:25 am
Nonstop2h 20m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 2/5
7:30 am-9:41 am
Nonstop3h 11m
Chicago O'Hare Intl
Sun 2/8
7:05 am-10:40 am
Nonstop2h 35m
$137
BostonChicago
BOS - ORD
BOSORD
Boston Logan Intl
Thu 1/29
7:30 am-9:41 am
Nonstop3h 11m
Chicago O'Hare Intl
Sat 1/31
7:05 am-10:40 am
Nonstop2h 35m
$137
Showing 1-10 of 60 results
Best time to book a flight from Massachusetts to Indiana
Have a flexible travel schedule? Discover the best time to fly to Indiana from Massachusetts 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 Massachusetts to Indiana
What is the cheapest month to book a flight from Massachusetts to Indiana?
Currently, June is the cheapest month in which you can book a flight from Massachusetts to Indiana (average of $89). Flying from Massachusetts to Indiana in February is currently the most expensive (average of $281). 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.
What is the cheapest time of day to fly from MA to IN?
Find hourly flight availability from Massachusetts to Indiana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 15, 2026.
It’s optimal to fly from Massachusetts to Indiana in the morning. By choosing this option you can save up to 57% on the cost of your flight, compared to a flight in the afternoon.
What is the cheapest day to fly from Massachusetts to Indiana?
Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Indiana. Price data was last updated on January 10, 2026.
Travelers seeking maximum savings on their Massachusetts to Indiana flight should consider departing on Tuesday evenings when fares are most often at their lowest. Sunday evenings flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Massachusetts to Indiana
Explore weekly flight availability from Massachusetts to Indiana. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 15, 2026.
The most flights from USMA to USIN are scheduled on a Thursday (15 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
Reviews of airlines servicing Indiana
Get insights into the airlines that provide service to Indiana. 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 Indiana. Reviews last updated January 15, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Massachusetts to Indiana to help guide your decision. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Comfort
8.0
Overall
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Massachusetts to Indiana. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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.
Alternative routes for Massachusetts to Indiana
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Massachusetts to Indiana
Discover the top 7 airlines that operate flights from Massachusetts to Indiana. 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 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$58 | Average$136 | FlexibilityNo cancel fee | On-time88% | |
| Cheapest$102 | Average$225 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$106 | Average$210 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$179 | Average$408 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$187 | Average$426 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$196 | Average$527 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$318 | Average$430 | FlexibilityNo cancel fee | On-time63% |