Massachusetts

$85+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Aug 1 — Aug 81
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Cheap 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 July 2, 2026.

This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:00 am
ORD
-
ACK
1 stop8h 24m
JetBlue
Wed 9/212:02 pm
ACK
-
ORD
1 stop6h 33m
JetBlue
Deal found 6/30$166
This Delta deal was found by Cheapflights users on 7/1. 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 9/54:30 pm
ORD
-
BOS
Nonstop2h 41m
Delta
Wed 9/98:50 pm
BOS
-
ORD
Nonstop2h 42m
Delta
Deal found 7/1$173
This Jetabroad deal was found by Cheapflights users on 6/30. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/69:35 am
ORD
-
BOS
1 stop6h 32m
JetBlue
Tue 8/112:45 pm
BOS
-
ORD
1 stop8h 13m
JetBlue
Deal found 6/30$174
This JetBlue deal was found by Cheapflights users on 7/1. 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 9/51:49 pm
ORD
-
BOS
Nonstop3h 10m
JetBlue
Sun 9/65:01 am
BOS
-
ORD
1 stop4h 47m
JetBlue
Deal found 7/1$175
This Southwest deal was found by Cheapflights users on 7/1. 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 7/317:35 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Tue 8/47:20 pm
BOS
-
MDW
Nonstop2h 40m
Southwest
Deal found 7/1$175
This Jetabroad deal was found by Cheapflights users on 6/28. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:00 am
ORD
-
BOS
1 stop7h 22m
JetBlue
Sun 7/265:01 am
BOS
-
ORD
1 stop4h 49m
JetBlue
Deal found 6/28$176
This JetBlue deal was found by Cheapflights users on 6/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/209:35 am
ORD
-
BOS
1 stop8h 24m
JetBlue
Tue 9/112:57 pm
BOS
-
ORD
1 stop5h 38m
JetBlue
Deal found 6/30$177
This Delta deal was found by Cheapflights users on 6/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:30 am
ORD
-
BOS
Nonstop2h 29m
Delta
Thu 9/107:30 am
BOS
-
ORD
Nonstop2h 54m
Delta
Deal found 6/30$178
This Southwest deal was found by Cheapflights users on 6/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/255:45 pm
MDW
-
BOS
Nonstop2h 25m
Southwest
Mon 7/275:25 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 6/29$178
This Delta deal was found by Cheapflights users on 7/1. 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 7/173:19 pm
ORD
-
BOS
Nonstop2h 40m
Delta
Wed 7/228:45 pm
BOS
-
ORD
Nonstop2h 54m
Delta
Deal found 7/1$179
This Southwest deal was found by Cheapflights users on 7/1. 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 7/282:40 pm
MDW
-
BOS
Nonstop2h 20m
Southwest
Fri 7/315:25 am
BOS
-
MDW
Nonstop2h 35m
Southwest
Deal found 7/1$179
This Cheapflightsfares deal was found by Cheapflights users on 6/28. 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 7/159:40 am
ORD
-
BOS
1 stop6h 37m
JetBlue
Sun 7/198:07 am
BOS
-
ORD
Nonstop2h 58m
JetBlue
Deal found 6/28$180

Find flight deals from Illinois to Massachusetts

Keep the following information in mind while searching for Illinois to Massachusetts flight deals. Data was last updated July 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$166
(JetBlue)

One-way from

$85
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$241

Good round-trip deal

$212 or less

Good one-way deal

$128 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
From Illinois to Massachusetts
One-way flight from Illinois to Massachusetts
Highest demand for flights based on searches. 3% potential increase in price ($8 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in July 2026
Price to beat on a round-trip flight from Illinois to Massachusetts.
Price to beat on a one-way flight from Illinois to Massachusetts.

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 July 2, 2026.
Use the filters below to find and compare flights from Illinois to Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 8/20

9:35 am-6:59 pm

1 stop8h 24m

Boston Logan Intl

Tue 9/1

12:57 pm-5:35 pm

1 stop5h 38m

$177

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 8/19

4:40 pm-10:15 pm

1 stop4h 35m

Boston Logan Intl

Fri 8/21

8:20 pm-10:00 pm

Nonstop2h 40m

$180

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/7

7:30 pm-11:00 pm

Nonstop2h 30m

Boston Logan Intl

Mon 8/10

7:30 am-9:26 am

Nonstop2h 56m

$191

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/14

10:30 am-2:07 pm

Nonstop2h 37m

Boston Logan Intl

Wed 7/15

8:15 pm-10:15 pm

Nonstop3h 00m

$191

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 7/14

10:30 am-2:07 pm

Nonstop2h 37m

Boston Logan Intl

Tue 7/21

5:45 am-9:36 am

1 stop4h 51m

$193

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 7/27

6:05 am-9:29 am

Nonstop2h 24m

Boston Logan Intl

Thu 7/30

6:00 am-7:58 am

Nonstop2h 58m

$199

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 9/26

6:30 am-2:40 pm

1 stop7h 10m

Boston Logan Intl

Tue 9/29

6:55 am-11:47 am

1 stop5h 52m

$201

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 8/21

6:00 am-2:43 pm

1 stop7h 43m

Boston Logan Intl

Wed 9/9

6:55 am-11:47 am

1 stop5h 52m

$201

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 7/17

6:00 pm-11:30 pm

1 stop4h 30m

Boston Logan Intl

Mon 7/20

5:25 am-7:00 am

Nonstop2h 35m

$205

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/10

12:52 pm-4:27 pm

Nonstop2h 35m

Boston Logan Intl

Sun 9/13

6:00 am-7:59 am

Nonstop2h 59m

$207

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/30

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 $183). Flying from Illinois to Massachusetts in June is currently the most expensive (average of $316). 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 July 2, 2026.

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 42% versus a flight in the morning.

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 July 2, 2026.

The most flights from USIL to USMA are scheduled on a Wednesday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 on average).

How much does it cost to fly round-trip from Illinois to Massachusetts?

How far ahead should I book a flight from Illinois to Massachusetts?

To ensure you get the cheapest price possible for a flight from Illinois to Massachusetts, you should look to book at least 60 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 June 27, 2026.

Travelers seeking maximum savings on their Illinois to Massachusetts flight should consider departing on Thursday afternoons 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.

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 July 2, 2026.
See what other customers who have flown with Southwest,Delta, andUnited 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.

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Bhoopal,Nov 2024

STL - BOS

Flight was delayed by one hour and 40 minutes. Also baggage was delivered late at Boston. This delay made me miss my connection from Boston to Hyderabad

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 $191, JetBlue can have you in Massachusetts from Illinois in 2h 30m. Illinois and Massachusetts are separated by a distance of 864 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $58. Users have also found prices from $61 and $66 on Southwest and United Airlines, 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 $183). Flying from Illinois to Massachusetts in June is currently the most expensive (average of $316). 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

Browse thousands of different options on Cheapflights for your next trip

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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.

Top 5 airlines flying from Illinois to Massachusetts

Discover the top 5 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 July 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$68Average$285FlexibilityNo cancel feeOn-time62%
DeltaCheapest$81Average$308FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$114Average$253FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$127Average$363FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$136Average$432FlexibilityNo cancel feeOn-time71%

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