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Massachusetts

$47+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$47
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$244

Good round-trip deal

$158 or less

Good one-way deal

$88 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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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 October 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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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 12/57:10 pmORD - BOS
Nonstop2h 24mDelta
Mon 12/87:52 pmBOS - ORD
Nonstop2h 55mDelta
Deal found 10/29$117
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 12/47:10 amORD - BOS
Nonstop2h 26mDelta
Sun 12/77:30 amBOS - ORD
Nonstop3h 03mDelta
Deal found 10/29$118
This Mytrip deal was found by Cheapflights users on 10/29. 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.
Thu 11/135:25 amORD - BOS
1 stop26h 03mFrontier
Mon 11/178:40 amBOS - ORD
1 stop15h 48mFrontier
Deal found 10/29$119
This Mytrip deal was found by Cheapflights users on 10/30. 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.
Thu 11/1310:12 amMDW - BOS
1 stop21h 16mFrontier
Sat 11/1511:43 amBOS - MDW
1 stop10h 52mFrontier
Deal found 10/30$119
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/183:08 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Sat 12/66:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Deal found 10/30$122
This Southwest deal was found by Cheapflights users on 10/30. 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 11/271:40 pmMDW - BOS
Nonstop2h 15mSouthwest
Thu 12/45:30 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 10/30$122
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/47:23 pmMDW - BOS
1 stop13h 59mFrontier
Sun 12/711:28 amBOS - MDW
1 stop23h 24mFrontier
Deal found 10/29$123
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Mon 12/155:12 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Thu 1/15:30 pmBOS - ORD
Nonstop3h 14mAmerican Airlines
Deal found 10/29$124
This Trip.com deal was found by Cheapflights users on 10/29. 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.
Wed 11/56:55 pmORD - BOS
Nonstop2h 32mJetBlue
Wed 11/128:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/29$125
This JetBlue deal was found by Cheapflights users on 10/29. 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 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
Wed 11/123:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 10/29$127
This Southwest deal was found by Cheapflights users on 10/30. 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 12/46:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sun 12/76:50 pmBOS - MDW
1 stop5h 40mSouthwest
Deal found 10/30$127
This Trip.com deal was found by Cheapflights users on 10/30. 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.
Thu 11/1311:20 amORD - BOS
Nonstop2h 24mJetBlue
Mon 11/173:55 pmBOS - ORD
Nonstop3h 00mJetBlue
Deal found 10/30$128

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 October 30, 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

Fri 12/5

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Mon 12/8

6:00 am-8:00 am

Nonstop3h 00m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/13

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Sun 12/14

4:05 pm-6:02 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Sun 12/7

4:05 pm-6:02 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 12/10

10:35 am-1:59 pm

Nonstop2h 24m

Boston Logan Intl

Sat 12/13

7:30 am-9:33 am

Nonstop3h 03m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/5

7:10 pm-10:34 pm

Nonstop2h 24m

Boston Logan Intl

Mon 12/8

7:52 pm-9:47 pm

Nonstop2h 55m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 12/6

10:35 am-1:59 pm

Nonstop2h 24m

Boston Logan Intl

Sun 12/7

12:50 pm-2:47 pm

Nonstop2h 57m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/16

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Tue 12/16

4:05 pm-6:02 pm

Nonstop2h 57m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/26

9:35 am-12:50 pm

Nonstop2h 15m

Boston Logan Intl

Wed 12/3

5:30 am-7:15 am

Nonstop2h 45m

$122

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 11/14

6:55 pm-10:27 pm

Nonstop2h 32m

Boston Logan Intl

Mon 11/17

3:55 pm-5:55 pm

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/18

9:20 am-12:53 pm

Nonstop2h 33m

Boston Logan Intl

Sun 12/21

4:15 pm-6:19 pm

Nonstop3h 04m

$131

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

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, November is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $71). Flying from Illinois to Massachusetts in February is currently the most expensive (average of $137). 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 October 30, 2025.

When flying from Illinois to Massachusetts, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 77% versus a flight in the morning.

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

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

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

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 October 30, 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
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
7,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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
2,906 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.1

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 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 $122, 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 Delta. According to our data, you can fly for as low as $59. Users have also found prices from $64 and $65 on Southwest and JetBlue, 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, November is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $71). Flying from Illinois to Massachusetts in February is currently the most expensive (average of $137). 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.

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$58Average$141FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$322FlexibilityNo cancel feeOn-time62%
DeltaCheapest$99Average$261FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$484FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$121Average$465FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$137Average$247FlexibilityNo cancel feeOn-time63%

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