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Massachusetts

$67+ Cheap flights from Illinois 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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Cheap flight deals from Illinois to Massachusetts

Keep the following information in mind while searching for Illinois to Massachusetts flight deals. Data was last updated September 15, 2025.

Round-trip from

$127
(Southwest)

One-way from

$67
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$207

Good round-trip deal

$168 or less

Good one-way deal

$68 or less
From Illinois to Massachusetts
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One-way flight from Illinois to Massachusetts
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Highest demand for flights based on searches. 6% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Illinois to Massachusetts.
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Price to beat on a one-way flight from Illinois to Massachusetts.
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Find flight deals from Illinois to Massachusetts

Cheapest flights from Illinois to Massachusetts
Explore the most affordable flight options available from Illinois to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/295:35 amMDW - BOS
1 stop4h 45mSouthwest
Wed 10/295:05 pmBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/15$127
This Priceline deal was found by Cheapflights users on 9/14. 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 9/267:50 pmORD - BOS
Nonstop2h 35mJetBlue
Wed 10/17:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 9/14$132
This Southwest deal was found by Cheapflights users on 9/14. 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 11/147:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Tue 11/187:45 amBOS - MDW
2 stops6h 15mSouthwest
Deal found 9/14$132
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/11:30 pmORD - BOS
Nonstop2h 32mUnited Airlines
Sun 10/56:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 9/14$133
This Southwest deal was found by Cheapflights users on 9/14. 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 11/76:45 amMDW - BOS
1 stop10h 25mSouthwest
Sun 11/95:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/14$133
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 10/2512:40 pmORD - BOS
1 stop7h 10mSouthwest
Tue 10/287:50 amBOS - ORD
1 stop5h 00mSouthwest
Deal found 9/13$134
This JetBlue deal was found by Cheapflights users on 9/14. 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.
Mon 10/207:13 pmORD - BOS
Nonstop2h 33mJetBlue
Sat 10/257:09 amBOS - ORD
Nonstop3h 13mJetBlue
Deal found 9/14$135
This Kiwi.com deal was found by Cheapflights users on 9/12. 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.
Tue 10/76:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Tue 10/146:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
Deal found 9/12$136
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 9/237:30 amORD - BOS
Nonstop2h 31mUnited Airlines
Tue 9/233:15 pmBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 9/14$137
This Southwest deal was found by Cheapflights users on 9/13. 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.
Wed 11/264:05 pmMDW - BOS
Nonstop2h 15mSouthwest
Fri 11/285:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 9/13$137
This Cheapflightsfares deal was found by Cheapflights users on 9/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Wed 10/292:15 pmBOS - ORD
1 stop8h 18mSpirit Airlines
Deal found 9/13$139
This Orbitz deal was found by Cheapflights users on 9/14. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:50 pmORD - BOS
1 stop12h 53mMultiple Airlines
Tue 10/73:00 pmBOS - ORD
1 stop9h 45mMultiple Airlines
Deal found 9/14$140

Cheapflights Fare Finder

 
Customize your flight search to find flights from Illinois 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 September 15, 2025.
Use the filters below to find and compare flights from Illinois to Massachusetts that are best for you.

Fly from

Illinois

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 10/12

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Thu 10/16

6:00 am-7:56 am

Nonstop2h 56m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/6

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

Tue 1/13

8:10 pm-10:15 pm

Nonstop3h 05m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/26

4:05 pm-7:20 pm

Nonstop2h 15m

Boston Logan Intl

Fri 11/28

5:15 am-7:00 am

Nonstop2h 45m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/26

4:00 pm-7:31 pm

Nonstop2h 31m

Boston Logan Intl

Sat 9/27

6:00 am-7:56 am

Nonstop2h 56m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 10/22

12:30 pm-5:45 pm

1 stop4h 15m

Boston Logan Intl

Wed 10/29

9:10 am-2:25 pm

1 stop6h 15m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/8

9:50 am-1:10 pm

Nonstop2h 20m

Boston Logan Intl

Sun 11/9

8:30 am-10:35 am

Nonstop3h 05m

$147

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/15

5:50 am-5:05 pm

2 stops10h 15m

Boston Logan Intl

Sun 11/16

6:50 am-3:40 pm

1 stop9h 50m

$148

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 9/30

11:25 am-10:15 pm

1 stop9h 50m

Boston Logan Intl

Sun 12/21

2:25 pm-4:10 pm

Nonstop2h 45m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/6

9:25 pm-12:45 am

Nonstop2h 20m

Boston Logan Intl

Sat 11/15

6:00 am-10:45 am

1 stop5h 45m

$155

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/8

7:00 am-10:33 am

Nonstop2h 33m

Boston Logan Intl

Thu 1/15

7:00 am-9:10 am

Nonstop3h 10m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results
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Best time to book a flight from Illinois to Massachusetts

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

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

Currently, January is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $218). Flying from Illinois to Massachusetts in July is currently the most expensive (average of $311). 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 IL to MA?

Find hourly flight availability from Illinois to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Massachusetts as you normally would.

Weekly flight availability from Illinois to Massachusetts

Explore weekly flight availability from Illinois to Massachusetts. 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 September 15, 2025.

The most flights from USIL to USMA are scheduled on a Monday (75 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (46 on average).

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 September 15, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Illinois to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,954 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,929 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,912 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Entertainment

7.5

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

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

  • How long is the flight from Illinois to Massachusetts?

    For as low as $137, United Airlines can have you in Massachusetts from Illinois in 2h 15m. Illinois and Massachusetts are separated by a distance of 857 mi. Generally, flights for this route are nonstop.

  • What are the cheapest airlines to fly from Illinois to Massachusetts one-way?

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $67. Users have also found prices from $69 and $69 on JetBlue and Southwest, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Illinois 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 Illinois to Massachusetts?

    Currently, January is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $218). Flying from Illinois to Massachusetts in July is currently the most expensive (average of $311). 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 Illinois to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Illinois to Massachusetts

Discover the top 7 airlines that operate flights from Illinois 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$37Average$152FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$288FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$260FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$483FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$132Average$448FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$141Average$262FlexibilityNo cancel feeOn-time63%

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