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$69+ 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 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$137
(JetBlue)

One-way from

$69
(Delta)

Popular in

April

Cheapest in

September

Average price

$227

Good round-trip deal

$137 or less

Good one-way deal

$68 or less
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. 8% potential increase in price ($21 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 July 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 July 31, 2025.

This JetBlue deal was found by Cheapflights users on 7/29. 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.
Fri 9/197:50 pmORD - BOS
Nonstop2h 35mJetBlue
Mon 9/227:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 7/29$137
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/42:35 pmMDW - BOS
1 stop7h 25mSouthwest
Wed 9/109:25 amBOS - MDW
Nonstop2h 40mSouthwest
Deal found 7/28$137
This American Airlines deal was found by Cheapflights users on 7/31. 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.
Sun 9/146:05 amORD - BOS
Nonstop2h 27mAmerican Airlines
Sun 9/215:00 amBOS - ORD
Nonstop2h 51mAmerican Airlines
Deal found 7/31$138
This United Airlines deal was found by Cheapflights users on 7/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Wed 9/39:43 amBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 7/29$139
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/198:12 pmORD - BOS
1 stop14h 06mSpirit Airlines
Tue 8/266:05 amBOS - ORD
1 stop14h 02mSpirit Airlines
Deal found 7/30$145
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 9/41:50 pmORD - BOS
1 stop7h 25mSouthwest
Wed 9/105:40 amBOS - ORD
1 stop7h 10mSouthwest
Deal found 7/29$146
This Delta deal was found by Cheapflights users on 7/31. 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 9/410:15 amORD - BOS
Nonstop2h 33mDelta
Wed 9/107:55 pmBOS - ORD
Nonstop3h 01mDelta
Deal found 7/31$147
This Priceline deal was found by Cheapflights users on 7/30. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/212:05 pmSTL - BDL
1 stop8h 11mSpirit Airlines
Sun 10/56:10 amBDL - STL
1 stop5h 40mSpirit Airlines
Deal found 7/30$159
This CheapOair deal was found by Cheapflights users on 7/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/208:12 pmORD - BOS
1 stop14h 06mMultiple Airlines
Sun 8/249:20 amBOS - ORD
1 stop10h 21mMultiple Airlines
Deal found 7/30$171
This American Airlines deal was found by Cheapflights users on 7/30. 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.
Sat 9/138:16 amORD - BDL
Nonstop2h 18mAmerican Airlines
Sun 9/146:43 amBDL - ORD
Nonstop2h 37mAmerican Airlines
Deal found 7/30$177
This Southwest deal was found by Cheapflights users on 7/31. 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 9/91:25 pmMDW - BDL
Nonstop2h 05mSouthwest
Wed 9/105:20 pmBDL - MDW
Nonstop2h 20mSouthwest
Deal found 7/31$177
This Mytrip deal was found by Cheapflights users on 7/30. 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.
Fri 10/245:17 pmORD - BDL
3 stops21h 54mSpirit Airlines
Mon 10/271:00 pmBDL - ORD
1 stop5h 38mSpirit Airlines
Deal found 7/30$183

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 31, 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 9/19

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

Mon 9/22

7:00 am-8:56 am

Nonstop2h 56m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 9/4

6:45 am-10:00 am

Nonstop2h 15m

Boston Logan Intl

Sat 9/6

5:20 am-11:10 am

1 stop6h 50m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 9/14

6:05 am-9:32 am

Nonstop2h 27m

Boston Logan Intl

Sun 9/21

5:00 am-6:51 am

Nonstop2h 51m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 8/31

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Wed 9/3

9:43 am-11:33 am

Nonstop2h 50m

$139

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/19

8:12 pm-11:18 am

1 stop14h 06m

Boston Logan Intl

Tue 8/26

6:05 am-7:07 pm

1 stop14h 02m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

1:50 pm-10:15 pm

1 stop7h 25m

Boston Logan Intl

Sat 9/6

2:50 pm-10:00 pm

1 stop8h 10m

$146

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/4

10:15 am-1:48 pm

Nonstop2h 33m

Boston Logan Intl

Sat 9/6

7:20 am-9:15 am

Nonstop2h 55m

$147

St. LouisHartford

STL - BDL

STLBDL

Lambert-St Louis

Thu 10/2

12:05 pm-9:16 pm

1 stop8h 11m

Hartford Bradley Intl

Sun 10/5

6:10 am-10:50 am

1 stop5h 40m

$159

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/20

8:12 pm-11:18 am

1 stop14h 06m

Boston Logan Intl

Sun 8/24

9:20 am-6:41 pm

1 stop10h 21m

$171

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Sat 9/13

8:16 am-11:34 am

Nonstop2h 18m

Hartford Bradley Intl

Sun 9/14

6:43 am-8:20 am

Nonstop2h 37m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

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 July 31, 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 July 31, 2025.

The most flights from USIL to USMA are scheduled on a Thursday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (22 on average).

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 31, 2025.
See what other customers who have flown with Alaska Airlines, Southwest, and Delta from Illinois to Massachusetts have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Southwest
8.0
Very good
4,246 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
Delta
8.0
Very good
7,981 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
United Airlines
7.4
Good
8,900 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.
American Airlines
7.2
Good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Entertainment

7.1

Boarding

8.1

Overall

8.0

Crew

8.5

Comfort

7.8

Reviews

1 / 20
10.0
Excellent

Jonathan,Jul 2025

SEA - BOS

Fantastic Check-in with easy baggage drop. While it took a while to find out which was the gate, the boarding was a dream, the stewards were simply incredible and the flight fantastic.

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 Delta. According to our data, you can fly for as low as $69. Users have also found prices from $69 and $75 on Southwest and Spirit 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, 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$35Average$100FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$381FlexibilityNo cancel feeOn-time62%
DeltaCheapest$90Average$256FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$122Average$488FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$131Average$438FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$263FlexibilityNo cancel feeOn-time63%

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