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$59+ 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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$59
(JetBlue)

Popular in

April

Cheapest in

September

Average price

$289

Good round-trip deal

$167 or less

Good one-way deal

$78 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. 11% potential increase in price ($29 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 17, 2025.

This JetBlue deal was found by Cheapflights users on 4/16. 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.
Wed 5/77:31 pmORD - BOS
Nonstop2h 29mJetBlue
Sun 5/116:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 4/16$117
This Southwest deal was found by Cheapflights users on 4/16. 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 5/27:20 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 5/47:40 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 4/16$117
This American Airlines deal was found by Cheapflights users on 4/17. 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 5/136:35 pmORD - BOS
Nonstop2h 32mAmerican Airlines
Sat 5/177:23 pmBOS - ORD
Nonstop3h 02mAmerican Airlines
Deal found 4/17$118
This Mytrip deal was found by Cheapflights users on 4/17. 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 5/1312:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Wed 5/143:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Deal found 4/17$121
This Southwest deal was found by Cheapflights users on 4/16. 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 5/61:50 pmORD - BOS
1 stop4h 20mSouthwest
Sun 5/115:45 amBOS - ORD
1 stop7h 05mSouthwest
Deal found 4/16$136
This United Airlines deal was found by Cheapflights users on 4/17. 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 6/59:30 pmORD - BOS
Nonstop2h 29mUnited Airlines
Mon 6/96:00 amBOS - ORD
Nonstop2h 58mUnited Airlines
Deal found 4/17$138
This Priceline deal was found by Cheapflights users on 4/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Wed 5/213:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Deal found 4/16$141
This Delta deal was found by Cheapflights users on 4/16. 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.
Tue 4/297:00 amORD - BOS
Nonstop2h 26mDelta
Sun 5/47:30 amBOS - ORD
Nonstop3h 00mDelta
Deal found 4/16$167
This CheapOair deal was found by Cheapflights users on 4/16. 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.
Thu 5/84:00 pmMDW - BOS
1 stop16h 34mFrontier
Wed 5/148:00 amBOS - MDW
1 stop29h 24mFrontier
Deal found 4/16$191
This Flightnetwork deal was found by Cheapflights users on 4/17. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/94:15 pmORD - BOS
1 stop7h 29mFrontier
Sun 5/1110:14 amBOS - ORD
1 stop28h 27mFrontier
Deal found 4/17$200
This Mytrip deal was found by Cheapflights users on 4/17. 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.
Fri 6/68:36 pmMDW - BOS
1 stop11h 36mAllegiant Air
Sun 6/811:31 amBOS - MDW
1 stop20h 44mAllegiant Air
Deal found 4/17$211
This American Airlines deal was found by Cheapflights users on 4/17. 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 6/256:00 amORD - ACK
1 stop5h 38mAmerican Airlines
Sat 6/285:16 pmACK - ORD
1 stop7h 08mAmerican Airlines
Deal found 4/17$218

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 April 17, 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

Wed 5/7

7:31 pm-11:00 pm

Nonstop2h 29m

Boston Logan Intl

Sun 5/11

6:00 am-8:00 am

Nonstop3h 00m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 5/2

7:20 pm-10:35 pm

Nonstop2h 15m

Boston Logan Intl

Sun 5/4

7:40 am-9:15 am

Nonstop2h 35m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/13

6:35 pm-10:07 pm

Nonstop2h 32m

Boston Logan Intl

Sat 5/17

7:23 pm-9:25 pm

Nonstop3h 02m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/13

5:05 am-2:44 pm

1 stop8h 39m

Boston Logan Intl

Tue 5/20

3:49 pm-11:04 pm

1 stop8h 15m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/6

1:50 pm-7:10 pm

1 stop4h 20m

Boston Logan Intl

Wed 5/7

6:05 am-11:50 am

1 stop6h 45m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/5

9:30 pm-12:59 am

Nonstop2h 29m

Boston Logan Intl

Mon 6/9

6:00 am-7:58 am

Nonstop2h 58m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Wed 5/21

3:49 pm-11:04 pm

1 stop8h 15m

$141

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/29

7:00 am-10:26 am

Nonstop2h 26m

Boston Logan Intl

Sun 5/4

7:30 am-9:30 am

Nonstop3h 00m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/8

4:00 pm-9:34 am

1 stop16h 34m

Boston Logan Intl

Wed 5/14

8:00 am-12:24 pm

1 stop29h 24m

$191

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/9

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Sun 5/11

10:14 am-1:41 pm

1 stop28h 27m

$200

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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, January is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $218). Flying from Illinois to Massachusetts in July is currently the most expensive (average of $311). 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 April 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Illinois to Massachusetts as you normally would.

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 April 17, 2025.

The most flights from USIL to USMA are scheduled on a Thursday (69 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 April 17, 2025.
Peruse reviews from past customers who have flown with Alaska Airlines, Southwest and Delta from Illinois to Massachusetts to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,887 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,887 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,916 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,887 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,887 reviews

Comfort

7.9

Boarding

8.1

Crew

8.5

Food

7.1

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • 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 $59. Users have also found prices from $60 and $68 on American Airlines and Southwest, 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, January is the cheapest month in which you can book a flight from Illinois to Massachusetts (average of $218). Flying from Illinois to Massachusetts in July is currently the most expensive (average of $311). 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 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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$299FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$115FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$80Average$490FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$478FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$145Average$459FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$293FlexibilityNo cancel feeOn-time63%

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