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$67+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$125
(Southwest)

One-way from

$67
(United Airlines)

Popular in

March

Cheapest in

September

Average price

$184

Good round-trip deal

$192 or less

Good one-way deal

$114 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. 7% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 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 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/11. 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 10/256:30 amBOS - MDW
2 stops10h 55mSouthwest
Mon 10/2711:25 amMDW - BOS
1 stop6h 50mSouthwest
Deal found 9/11$125
This United Airlines deal was found by Cheapflights users on 9/10. 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 10/89:53 amBOS - ORD
Nonstop2h 50mUnited Airlines
Tue 10/149:00 amORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 9/10$125
This Southwest deal was found by Cheapflights users on 9/11. 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 10/315:00 amBOS - MDW
Nonstop2h 40mSouthwest
Mon 11/36:40 amMDW - BOS
1 stop8h 55mSouthwest
Deal found 9/11$126
This Cheapflightsfares deal was found by Cheapflights users on 9/11. 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.
Wed 10/156:16 amBOS - ORD
1 stop13h 22mSpirit Airlines
Tue 10/216:00 amORD - BOS
1 stop6h 20mSpirit Airlines
Deal found 9/11$126
This Delta deal was found by Cheapflights users on 9/10. 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 10/259:00 amBOS - ORD
1 stop4h 40mDelta
Mon 10/277:10 pmORD - BOS
Nonstop2h 35mDelta
Deal found 9/10$127
This Southwest deal was found by Cheapflights users on 9/10. 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.
Tue 11/45:35 pmBOS - MDW
1 stop4h 30mSouthwest
Wed 11/58:25 amMDW - BOS
2 stops7h 10mSouthwest
Deal found 9/10$129
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Tue 10/76:57 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Sun 10/127:00 amORD - BOS
Nonstop2h 21mAmerican Airlines
Deal found 9/10$129
This Southwest deal was found by Cheapflights users on 9/9. 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 10/256:30 amBOS - MDW
2 stops10h 55mSouthwest
Mon 11/36:40 amMDW - BOS
1 stop8h 55mSouthwest
Deal found 9/9$130
This Southwest deal was found by Cheapflights users on 9/11. 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 10/296:45 amBOS - ORD
1 stop8h 15mSouthwest
Wed 11/121:45 pmORD - BOS
1 stop7h 30mSouthwest
Deal found 9/11$130
This Southwest deal was found by Cheapflights users on 9/11. 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 10/305:15 amBOS - MDW
Nonstop2h 40mSouthwest
Sun 11/25:45 amMDW - BOS
1 stop10h 25mSouthwest
Deal found 9/11$131
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Fri 10/34:25 pmBOS - ORD
Nonstop2h 55mUnited Airlines
Sun 10/1211:05 amORD - BOS
Nonstop2h 35mUnited Airlines
Deal found 9/10$131
This Southwest deal was found by Cheapflights users on 9/11. 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 10/249:35 pmBOS - MDW
Nonstop2h 40mSouthwest
Sun 10/266:05 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 9/11$132

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 September 11, 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

Fri 10/31

5:00 am-6:40 am

Nonstop2h 40m

Chicago Midway

Mon 11/3

6:40 am-4:35 pm

1 stop8h 55m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 10/29

6:45 am-2:00 pm

1 stop8h 15m

Chicago O'Hare Intl

Wed 11/12

1:45 pm-10:15 pm

1 stop7h 30m

$130

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 9/30

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 10/1

7:50 pm-11:25 pm

Nonstop2h 35m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 11/13

5:29 am-8:52 am

1 stop4h 23m

Chicago Midway

Mon 11/17

6:48 pm-11:55 pm

1 stop4h 07m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/15

5:34 am-8:40 am

1 stop4h 06m

Chicago Midway

Tue 10/21

1:08 pm-8:01 pm

1 stop5h 53m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 11/10

1:45 pm-3:30 pm

Nonstop2h 45m

Chicago Midway

Fri 11/14

7:15 pm-10:30 pm

Nonstop2h 15m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 11/1

5:45 am-1:08 pm

1 stop8h 23m

Chicago Midway

Sat 11/8

1:06 pm-5:52 pm

1 stop3h 46m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 10/15

5:15 am-6:55 am

Nonstop2h 40m

Chicago Midway

Sat 10/18

12:45 pm-4:00 pm

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/25

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Wed 10/1

7:50 pm-11:25 pm

Nonstop2h 35m

$140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/25

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Tue 9/30

9:51 am-1:20 pm

Nonstop2h 29m

$140

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 September 11, 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 September 11, 2025.

The most flights from USMA to USIL are scheduled on a Thursday (77 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 September 11, 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
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

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
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

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
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

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
2,913 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Crew

8.6

Comfort

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, JetBlue, and Delta fly from Massachusetts to Illinois in about 2h 40m. The time it takes to get you to your destination can typically vary by up to 1h 43m. Airlines will cover a distance of 857 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 United Airlines, with whom users have recently found tickets for as low as $67. However, be on the lookout for offers from Southwest and Delta, 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$203FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$81Average$199FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$97Average$456FlexibilityNo cancel feeOn-time69%
DeltaCheapest$98Average$356FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$107FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$121Average$233FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$137Average$433FlexibilityNo cancel feeOn-time71%

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