Massachusetts

$53+ 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 2/10. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
Dec 27 — Jan 31
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Cheap flight deals from Illinois to Massachusetts

Discover tips and strategies to find the most affordable flight options for your journey from Illinois (USIL) to Massachusetts (USMA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 22, 2024.

Round-trip from

$119
(Kiwi.com)

One-way from

$53
(Mytrip)
From Illinois to Massachusetts
One-way flight from Illinois to Massachusetts

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 December 22, 2024.

This FlightHub deal was found by Cheapflights users on 12/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/227:00 amORD - BOS
1 stop9h 26mMultiple Airlines
Wed 12/2511:10 amBOS - ORD
1 stop11h 17mMultiple Airlines
Deal found 12/20$222
This American Airlines deal was found by Cheapflights users on 12/20. 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.
Fri 12/275:42 pmORD - BOS
1 stop4h 10mAmerican Airlines
Wed 1/16:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 12/20$228
This Mytrip deal was found by Cheapflights users on 12/21. 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.
Mon 12/302:20 pmMDW - BOS
1 stop9h 21mFrontier
Sat 1/256:00 amBOS - MDW
1 stop29h 02mFrontier
Deal found 12/21$242
This Southwest deal was found by Cheapflights users on 12/21. 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 12/256:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Tue 1/78:10 amBOS - MDW
Nonstop2h 55mSouthwest
Deal found 12/21$253
This Mytrip deal was found by Cheapflights users on 12/21. 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 12/315:33 pmORD - BOS
1 stop6h 02mFrontier
Tue 1/76:00 amBOS - ORD
1 stop8h 34mFrontier
Deal found 12/21$258
This FlightHub deal was found by Cheapflights users on 12/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/245:11 pmORD - BOS
1 stop17h 14mSpirit Airlines
Sat 12/286:27 amBOS - ORD
1 stop13h 52mSpirit Airlines
Deal found 12/21$273
This Delta deal was found by Cheapflights users on 12/21. 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 12/2710:05 amORD - BOS
1 stop8h 06mDelta
Mon 1/68:20 pmBOS - ORD
Nonstop3h 03mDelta
Deal found 12/21$283
This American Airlines deal was found by Cheapflights users on 12/21. 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 12/313:45 pmORD - BDL
Nonstop2h 07mAmerican Airlines
Wed 1/87:05 amBDL - ORD
Nonstop2h 49mAmerican Airlines
Deal found 12/21$295
This Delta deal was found by Cheapflights users on 12/21. 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 12/315:30 pmORD - ALB
1 stop4h 50mDelta
Mon 1/65:45 amALB - ORD
1 stop6h 08mDelta
Deal found 12/21$298
This JetBlue Airways deal was found by Cheapflights users on 12/21. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2410:11 amORD - BOS
1 stop8h 04mJetBlue
Sat 1/46:00 amBOS - ORD
Nonstop3h 07mJetBlue
Deal found 12/21$306
This Delta deal was found by Cheapflights users on 12/21. 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 12/316:29 amSTL - BDL
1 stop4h 29mDelta
Wed 1/17:30 amBDL - STL
1 stop5h 39mDelta
Deal found 12/21$306
This Delta deal was found by Cheapflights users on 12/21. 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 12/317:00 amORD - BDL
1 stop3h 58mDelta
Tue 1/75:14 pmBDL - ORD
1 stop4h 39mDelta
Deal found 12/21$314

Find flights from Illinois to Massachusetts within your budget

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 December 22, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/10

4:53 pm-12:30 am

1 stop6h 37m

Boston Logan Intl

Tue 1/14

6:00 am-1:34 pm

1 stop8h 34m

$119

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 2/9

4:18 pm-12:27 am

1 stop7h 09m

Boston Logan Intl

Wed 2/12

10:03 am-10:03 pm

1 stop13h 00m

$123

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sun 1/26

10:58 am-12:27 am

1 stop12h 29m

Boston Logan Intl

Fri 2/7

6:00 am-2:42 pm

1 stop9h 42m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/1

12:25 pm-10:00 pm

1 stop8h 35m

Boston Logan Intl

Wed 2/5

6:25 am-4:10 pm

1 stop10h 45m

$144

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 1/11

7:35 am-12:30 am

1 stop15h 55m

Boston Logan Intl

Mon 1/13

3:50 pm-4:14 pm

1 stop25h 24m

$152

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/11

7:00 am-10:15 am

Nonstop2h 15m

Boston Logan Intl

Tue 1/14

6:10 am-8:14 am

Nonstop3h 04m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 1/17

7:00 pm-10:15 pm

Nonstop2h 15m

Boston Logan Intl

Sun 1/19

8:10 am-10:05 am

Nonstop2h 55m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/11

6:00 am-9:33 am

Nonstop2h 33m

Boston Logan Intl

Mon 1/13

8:45 am-10:45 am

Nonstop3h 00m

$168

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/20

7:10 am-10:47 am

Nonstop2h 37m

Boston Logan Intl

Fri 1/24

7:15 am-9:25 am

Nonstop3h 10m

$187

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 2/4

4:22 pm-2:01 pm

1 stop20h 39m

Worcester

Tue 2/11

2:31 pm-10:47 am

1 stop21h 16m

$215

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/21

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.

Travel insights for flights from Illinois to Massachusetts

Get recent, data-driven insights about flights from Illinois to Massachusetts including ideal travel times, pricing trends, and more.

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 December 22, 2024.

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 December 22, 2024.

The most flights from USIL to USMA are scheduled on a Friday (47 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (15 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 December 22, 2024.
Peruse reviews from past customers who have flown with American Airlines, Frontier 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.
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,804 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,537 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,594 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.5
Good
3,789 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,265 reviews
8.1
Very good
4,804 reviews

Food

7.2

Overall

8.1

Comfort

8.1

Entertainment

7.7

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier. According to our data, you can fly for as low as $53. Users have also found prices from $79 and $79 on Delta 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.

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 December 22, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$315FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$116FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$84Average$556FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$138Average$492FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$149Average$478FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$275FlexibilityNo cancel feeOn-time63%
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