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$68+ Cheap flights from Massachusetts to Illinois

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 10/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Aug 27 — Sep 31
Wed 8/27
Wed 9/3
1 adult, Economy
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Cheap flight deals from Massachusetts to Illinois

Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated August 22, 2025.

Round-trip from

$132
(Southwest)

One-way from

$68
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$223

Good round-trip deal

$194 or less

Good one-way deal

$146 or less
From Massachusetts to Illinois
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One-way flight from Massachusetts to Illinois
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Highest demand for flights based on searches. 8% potential increase in price ($20 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 August 2025
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Price to beat on a round-trip flight from Massachusetts to Illinois.
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Price to beat on a one-way flight from Massachusetts to Illinois.
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Find flight deals from Massachusetts to Illinois

Cheapest flights from Massachusetts to Illinois
Explore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2025.

This Southwest deal was found by Cheapflights users on 8/18. 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.
Thu 9/185:35 amBOS - MDW
1 stop4h 25mSouthwest
Mon 9/227:15 amMDW - BOS
1 stop8h 10mSouthwest
Deal found 8/18$132
This Southwest deal was found by Cheapflights users on 8/21. 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 10/175:35 amBOS - ORD
1 stop8h 10mSouthwest
Sat 10/181:30 pmORD - BOS
1 stop4h 20mSouthwest
Deal found 8/21$132
This Cheapflightsfares deal was found by Cheapflights users on 8/20. 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 9/1612:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Sat 9/2011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/20$135
This Southwest deal was found by Cheapflights users on 8/20. 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.
Thu 9/1812:15 pmBOS - MDW
Nonstop2h 35mSouthwest
Sun 9/218:35 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 8/20$137
This JetBlue deal was found by Cheapflights users on 8/21. 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 11/245:35 pmBOS - ORD
Nonstop3h 15mJetBlue
Thu 11/2712:28 pmORD - BOS
Nonstop2h 26mJetBlue
Deal found 8/21$137
This Southwest deal was found by Cheapflights users on 8/18. 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.
Mon 9/225:35 amBOS - MDW
2 stops8h 35mSouthwest
Wed 9/246:25 amMDW - BOS
1 stop8h 00mSouthwest
Deal found 8/18$138
This CheapOair deal was found by Cheapflights users on 8/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/36:05 amBOS - ORD
1 stop14h 02mSpirit Airlines
Wed 9/1011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Deal found 8/20$138
This JetBlue deal was found by Cheapflights users on 8/21. 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 10/27:00 amBOS - ORD
Nonstop2h 56mJetBlue
Mon 10/66:50 pmORD - BOS
Nonstop2h 33mJetBlue
Deal found 8/21$142
This Southwest deal was found by Cheapflights users on 8/20. 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 12/35:35 pmBOS - MDW
1 stop4h 30mSouthwest
Sun 12/77:15 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 8/20$143
This JetBlue deal was found by Cheapflights users on 8/21. 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.
Fri 9/57:00 amBOS - ORD
Nonstop2h 56mJetBlue
Tue 9/99:51 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 8/21$143
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/163:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Wed 9/175:05 amORD - BOS
1 stop17h 52mSpirit Airlines
Deal found 8/20$145
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/41:00 pmBOS - ORD
1 stop5h 10mUnited Airlines
Sun 9/76:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 8/21$147

Cheapflights Fare Finder

 
Customize your flight search to find flights from Massachusetts to Illinois 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 August 22, 2025.
Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.

Fly from

Massachusetts

Fly to

Illinois

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/18

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Mon 9/22

7:15 am-4:25 pm

1 stop8h 10m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:20 am-9:15 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 9/7

7:00 am-10:30 am

Nonstop2h 30m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 10/7

7:50 am-2:25 pm

1 stop7h 35m

Chicago Midway

Sun 10/12

6:05 am-9:20 am

Nonstop2h 15m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/1

7:20 am-9:16 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 9/3

6:00 pm-9:38 pm

Nonstop2h 38m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 9/22

5:35 am-9:00 am

1 stop4h 25m

Chicago Midway

Wed 9/24

6:25 am-3:25 pm

1 stop8h 00m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/17

5:35 am-12:45 pm

1 stop8h 10m

Chicago O'Hare Intl

Sat 10/18

1:30 pm-6:50 pm

1 stop4h 20m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/9

7:00 am-8:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Sun 10/12

9:42 am-1:10 pm

Nonstop2h 28m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/28

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Sun 8/31

5:36 pm-9:12 pm

Nonstop2h 36m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 10/25

5:20 am-7:00 am

Nonstop2h 40m

Chicago Midway

Wed 10/29

6:05 am-9:20 am

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/3

9:35 pm-11:15 pm

Nonstop2h 40m

Chicago Midway

Mon 10/6

9:20 pm-12:40 am

Nonstop2h 20m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

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

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

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

Currently, August is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $245). Flying from Massachusetts to Illinois in March is currently the most expensive (average of $321). 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 IL?

Find hourly flight availability from Massachusetts to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 22, 2025.

When flying from Massachusetts to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Massachusetts to Illinois

Explore weekly flight availability from Massachusetts to Illinois. 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 August 22, 2025.

The most flights from USMA to USIL are scheduled on a Thursday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (24 on average).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated August 22, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Massachusetts to Illinois have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
4,245 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
7,981 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
8,930 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
4,245 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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
2,916 reviews
Southwest
8.0
Very good
4,245 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Crew

8.6

Overall

8.0

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 Massachusetts to Illinois. 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 Massachusetts to Illinois?

    Airlines like Southwest, Delta, and JetBlue fly from Massachusetts to Illinois in about 2h 55m. The time it takes to get you to your destination can typically vary by up to 1h 30m. Airlines will cover a distance of 864 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $68. However, be on the lookout for offers from Southwest and American Airlines, as they are both options that can get you from Massachusetts to Illinois for a low price.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $245). Flying from Massachusetts to Illinois in March is currently the most expensive (average of $321). 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 Massachusetts to Illinois

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

Discover the top 7 airlines that operate flights from Massachusetts to Illinois. 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 August 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$32Average$173FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$77Average$204FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$97Average$467FlexibilityNo cancel feeOn-time69%
DeltaCheapest$99Average$356FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$107FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$120Average$228FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$137Average$427FlexibilityNo cancel feeOn-time71%

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