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$59+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
1 adult, Economy
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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 November 6, 2025.

This Southwest deal was found by Cheapflights users on 11/5. 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 12/55:30 amBOS - MDW
Nonstop2h 45mSouthwest
Mon 12/86:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 11/5$117
This Delta deal was found by Cheapflights users on 11/6. 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.
Fri 12/127:52 pmBOS - ORD
Nonstop2h 55mDelta
Sun 12/147:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 11/6$117
This Southwest deal was found by Cheapflights users on 11/6. 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.
Sun 12/76:55 pmBOS - MDW
Nonstop2h 50mSouthwest
Tue 12/912:55 pmMDW - BOS
1 stop7h 10mSouthwest
Deal found 11/6$118
This American Airlines deal was found by Cheapflights users on 11/5. 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.
Wed 11/127:19 pmBOS - ORD
Nonstop3h 06mAmerican Airlines
Wed 12/38:40 pmORD - BOS
Nonstop2h 33mAmerican Airlines
Deal found 11/5$118
This Kissandfly.com deal was found by Cheapflights users on 11/6. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/158:30 amBOS - ORD
Nonstop3h 05mJetBlue
Wed 12/177:00 amORD - BOS
1 stop7h 14mJetBlue
Deal found 11/6$119
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
Thu 12/1111:28 amBOS - ORD
1 stop6h 59mFrontier
Thu 12/256:00 amORD - BOS
1 stop18h 19mFrontier
Deal found 11/5$120
This Southwest deal was found by Cheapflights users on 11/5. 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 12/45:30 amBOS - MDW
Nonstop2h 45mSouthwest
Mon 12/86:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Deal found 11/5$122
This JetBlue deal was found by Cheapflights users on 11/6. 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 12/45:29 pmBOS - ORD
Nonstop3h 14mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/6$122
This Southwest deal was found by Cheapflights users on 11/5. 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 12/27:45 amBOS - MDW
2 stops6h 15mSouthwest
Wed 12/36:20 amMDW - BOS
1 stop4h 25mSouthwest
Deal found 11/5$124
This Delta deal was found by Cheapflights users on 11/6. 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.
Fri 12/127:52 pmBOS - ORD
Nonstop2h 55mDelta
Fri 12/197:10 amORD - BOS
Nonstop2h 26mDelta
Deal found 11/6$124
This Trip.com deal was found by Cheapflights users on 11/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/98:30 amBOS - ORD
Nonstop3h 05mJetBlue
Tue 12/1611:25 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 11/6$125
This JetBlue deal was found by Cheapflights users on 11/6. 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.
Sat 12/63:40 pmBOS - ORD
1 stop7h 12mJetBlue
Mon 12/88:38 pmORD - BOS
Nonstop2h 28mJetBlue
Deal found 11/6$126

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 November 6, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$117
(Southwest)

One-way from

$59
(Southwest)

Popular in

April

Cheapest in

September

Average price

$248

Good round-trip deal

$191 or less

Good one-way deal

$123 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Massachusetts to Illinois
Search Deals
One-way flight from Massachusetts to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Illinois.
Search Deals
Price to beat on a one-way flight from Massachusetts to Illinois.
Search Deals

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 November 6, 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

Wed 12/10

8:30 am-12:45 pm

1 stop5h 15m

Chicago Midway

Fri 12/12

7:15 pm-10:30 pm

Nonstop2h 15m

$118

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/12

6:50 pm-11:30 pm

1 stop5h 40m

Chicago Midway

Mon 12/15

6:15 pm-9:35 pm

Nonstop2h 20m

$118

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 12/11

8:30 am-10:35 am

Nonstop3h 05m

Chicago O'Hare Intl

Fri 12/26

7:41 pm-11:10 pm

Nonstop2h 29m

$122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/6

3:40 pm-9:52 pm

1 stop7h 12m

Chicago O'Hare Intl

Mon 12/8

8:38 pm-12:06 am

Nonstop2h 28m

$126

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

6:00 pm-10:35 pm

1 stop5h 35m

Chicago Midway

Sun 12/7

7:15 pm-10:30 pm

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 11/21

5:00 am-12:15 pm

1 stop8h 15m

Chicago O'Hare Intl

Tue 12/2

1:45 pm-10:15 pm

1 stop7h 30m

$133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/9

9:40 am-11:40 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 12/22

9:12 pm-12:45 am

Nonstop2h 33m

$136

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 12/11

9:00 am-12:34 pm

1 stop4h 34m

Chicago Midway

Mon 12/15

1:14 pm-8:00 pm

1 stop5h 46m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 11/19

1:35 pm-3:20 pm

Nonstop2h 45m

Chicago Midway

Thu 11/20

12:55 pm-9:05 pm

1 stop7h 10m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 12/5

6:00 pm-10:35 pm

1 stop5h 35m

Chicago Midway

Tue 12/9

5:35 am-1:30 pm

1 stop6h 55m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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, November is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $89). Flying from Massachusetts to Illinois in February is currently the most expensive (average of $124). 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 November 6, 2025.

A simple way to save on the total cost of your ticket is to fly from Massachusetts to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 60% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Massachusetts to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Illinois. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Illinois flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

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 November 6, 2025.

The most flights from USMA to USIL are scheduled on a Thursday (68 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (25 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 November 6, 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
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
9,007 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
11,040 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
2,907 reviews
Southwest
8.0
Very good
4,240 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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 United Airlines fly from Massachusetts to Illinois in about 3h. The time it takes to get you to your destination can typically vary by up to 2h 15m. 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 Southwest, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Delta and United 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, November is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $89). Flying from Massachusetts to Illinois in February is currently the most expensive (average of $124). 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$71Average$255FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$79Average$195FlexibilityNo cancel feeOn-time62%
FrontierCheapest$89Average$116FlexibilityNo cancel feeOn-time62%
DeltaCheapest$116Average$286FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$238FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$126Average$495FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$135Average$433FlexibilityNo cancel feeOn-time71%

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