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$76+ 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 4/21. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$131
(Kiwi.com)

One-way from

$76
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$278

Good round-trip deal

$201 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. 15% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/26. 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.
Wed 5/1412:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Mon 5/1910:30 amBOS - ORD
1 stop6h 55mSpirit Airlines
Deal found 3/26$131
This JetBlue deal was found by Cheapflights users on 3/27. 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 5/18:50 amORD - BOS
Nonstop2h 28mJetBlue
Tue 5/64:30 pmBOS - ORD
Nonstop3h 06mJetBlue
Deal found 3/27$132
This Southwest deal was found by Cheapflights users on 3/27. 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.
Wed 4/94:00 pmORD - BOS
2 stops14h 50mSouthwest
Mon 4/145:00 amBOS - ORD
1 stop8h 45mSouthwest
Deal found 3/27$133
This American Airlines deal was found by Cheapflights users on 3/27. 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 4/228:05 amORD - BOS
Nonstop2h 25mAmerican Airlines
Fri 4/255:00 amBOS - ORD
Nonstop3h 00mAmerican Airlines
Deal found 3/27$138
This United Airlines deal was found by Cheapflights users on 3/26. 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.
Sat 6/146:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Sun 6/226:00 amBOS - ORD
Nonstop2h 58mUnited Airlines
Deal found 3/26$148
This CheapOair deal was found by Cheapflights users on 3/27. 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.
Mon 4/215:31 pmORD - BOS
1 stop6h 00mMultiple Airlines
Tue 4/2912:29 pmBOS - ORD
1 stop12h 51mMultiple Airlines
Deal found 3/27$151
This Southwest deal was found by Cheapflights users on 3/27. 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 4/105:30 amMDW - BOS
Nonstop2h 15mSouthwest
Mon 4/145:45 amBOS - MDW
Nonstop2h 35mSouthwest
Deal found 3/27$157
This Delta deal was found by Cheapflights users on 3/27. 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 4/46:55 pmORD - BOS
Nonstop2h 31mDelta
Mon 4/77:25 amBOS - ORD
Nonstop3h 02mDelta
Deal found 3/27$167
This Frontier deal was found by Cheapflights users on 3/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/151:19 pmMDW - BOS
1 stop10h 46mFrontier
Sun 5/1810:14 amBOS - MDW
1 stop13h 26mFrontier
Deal found 3/27$198
This CheapOair deal was found by Cheapflights users on 3/27. 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 4/178:10 amORD - BOS
1 stop24h 25mFrontier
Sun 4/205:30 amBOS - ORD
1 stop9h 03mFrontier
Deal found 3/27$230
This Mytrip deal was found by Cheapflights users on 3/26. 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 5/89:55 amORD - BDL
1 stop24h 27mSpirit Airlines
Sun 5/1112:27 pmBDL - ORD
1 stop21h 23mSpirit Airlines
Deal found 3/26$231
This Mytrip deal was found by Cheapflights users on 3/27. 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 5/308:04 pmMDW - BOS
1 stop12h 08mAllegiant Air
Sun 6/111:31 amBOS - MDW
1 stop27h 55mAllegiant Air
Deal found 3/27$235

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 March 28, 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 5/14

12:41 pm-11:29 pm

1 stop9h 48m

Boston Logan Intl

Mon 5/19

10:30 am-4:25 pm

1 stop6h 55m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/1

8:50 am-12:18 pm

Nonstop2h 28m

Boston Logan Intl

Tue 5/6

4:30 pm-6:36 pm

Nonstop3h 06m

$132

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/9

4:00 pm-7:50 am

2 stops14h 50m

Boston Logan Intl

Mon 4/14

5:00 am-12:45 pm

1 stop8h 45m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/22

8:05 am-11:30 am

Nonstop2h 25m

Boston Logan Intl

Fri 4/25

5:00 am-7:00 am

Nonstop3h 00m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 6/14

6:30 am-9:56 am

Nonstop2h 26m

Boston Logan Intl

Sun 6/22

6:00 am-7:58 am

Nonstop2h 58m

$148

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 4/21

5:31 pm-12:31 am

1 stop6h 00m

Boston Logan Intl

Tue 4/29

12:29 pm-12:20 am

1 stop12h 51m

$151

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 4/10

5:30 am-8:45 am

Nonstop2h 15m

Boston Logan Intl

Mon 4/14

5:45 am-7:20 am

Nonstop2h 35m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 4/4

6:55 pm-10:26 pm

Nonstop2h 31m

Boston Logan Intl

Mon 4/7

7:25 am-9:27 am

Nonstop3h 02m

$167

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/15

1:19 pm-1:05 am

1 stop10h 46m

Boston Logan Intl

Sun 5/18

10:14 am-10:40 pm

1 stop13h 26m

$198

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 4/17

8:10 am-9:35 am

1 stop24h 25m

Boston Logan Intl

Sun 4/20

5:30 am-1:33 pm

1 stop9h 03m

$230

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March 28, 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 March 28, 2025.

The most flights from USIL to USMA are scheduled on a Thursday (64 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (3 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 March 28, 2025.
Peruse reviews from past customers who have flown with Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Avelo Airlines
7.5
Good
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,273 reviews

Overall

8.1

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Crew

8.6

Food

7.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 United Airlines. According to our data, you can fly for as low as $76. Users have also found prices from $76 and $77 on Southwest and American 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$302FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$115FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$83Average$494FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$144Average$482FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$157Average$463FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$286FlexibilityNo cancel feeOn-time63%
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