HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$46+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — BOS
nov. 5 — nov. 121
1 adult
mar. 11/5
mar. 11/12
We work with more than 300 partners to bring you better travel deals

...and more

Find cheap flights from Illinois to Massachusetts with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 octubre 31, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/154:38 pmORD - BOS
Nonstop2h 19mSpirit Airlines
sáb. 11/235:30 amBOS - ORD
Nonstop3h 07mSpirit Airlines
Deal found 10/30$91
This CheapOair deal was found by Cheapflights users on 10/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/77:05 pmORD - BOS
1 stop4h 26mMultiple Airlines
mar. 11/127:40 amBOS - ORD
Nonstop3h 10mMultiple Airlines
Deal found 10/31$97
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/21:39 pmORD - BOS
1 stop9h 49mFrontier
mié. 11/66:00 amBOS - ORD
1 stop8h 32mFrontier
Deal found 10/29$100
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/412:57 pmMDW - BOS
1 stop10h 33mFrontier
mar. 12/106:00 amBOS - MDW
1 stop6h 42mFrontier
Deal found 10/30$105
This JetBlue deal was found by Cheapflights users on 10/31. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/48:50 amORD - BOS
Nonstop2h 22mJetBlue
lun. 12/96:00 amBOS - ORD
Nonstop3h 06mJetBlue
Deal found 10/31$117
This Delta deal was found by Cheapflights users on 10/31. 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.
jue. 11/146:40 amORD - BOS
Nonstop2h 20mDelta
lun. 11/183:45 pmBOS - ORD
Nonstop3h 01mDelta
Deal found 10/31$118
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/67:30 amORD - BOS
Nonstop2h 19mUnited Airlines
dom. 12/86:00 amBOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 10/30$123
This Southwest deal was found by Cheapflights users on 10/29. 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.
vie. 12/138:30 pmMDW - BOS
Nonstop2h 10mSouthwest
dom. 12/156:40 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 10/29$124
This American Airlines deal was found by Cheapflights users on 10/30. 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.
mié. 12/258:05 amORD - BOS
Nonstop2h 21mAmerican Airlines
vie. 1/38:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 10/30$158
This FareScan deal was found by Cheapflights users on 10/30. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/197:49 amORD - BDL
2 stops32h 12mSpirit Airlines
vie. 11/225:55 pmBDL - ORD
2 stops29h 11mSpirit Airlines
Deal found 10/30$184
This CheapOair deal was found by Cheapflights users on 10/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/258:21 pmORD - BDL
1 stop13h 08mMultiple Airlines
mar. 12/106:00 amBDL - ORD
1 stop16h 07mMultiple Airlines
Deal found 10/31$198
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/1811:25 amORD - BOS
2 stops6h 40mSouthwest
mar. 11/196:00 amBOS - ORD
2 stops8h 00mSouthwest
Deal found 10/30$199

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 2,570,725 searches. Data last updated octubre 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

dom. 1/19

4:21 pm-12:29 am

1 stop7h 08m

$69

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 12/4

11:45 am-12:38 am

1 stop11h 53m

$70

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

dom. 1/12

6:30 am-9:58 am

Nonstop2h 28m

$79

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 11/9

3:45 pm-7:06 pm

Nonstop2h 21m

$81

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 12/6

7:15 am-1:00 pm

1 stop4h 45m

$81

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 11/26

6:00 am-9:17 am

Nonstop2h 17m

$89

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

mar. 12/3

5:00 am-11:17 pm

2 stops17h 17m

$99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 11/12

7:00 am-10:20 am

Nonstop2h 20m

$101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

dom. 1/19

7:00 am-10:46 am

1 stop26h 46m

$72

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 12/21

8:05 pm-11:09 pm

1 stop26h 04m

$188

Flights are sorted by cheapest first

Deals found on 10/29

Showing 1-10 of 60 results
1
2
3
...
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.

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 octubre 31, 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.

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 octubre 31, 2024.
Peruse reviews from past customers who have flown with American Airlines, Spirit Airlines and Southwest 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
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,116 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,420 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,835 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Qatar Airways
7.5
Good
3,900 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,514 reviews
Southwest
8.1
Very good
5,116 reviews

Boarding

8.3

Crew

8.7

Entertainment

7.7

Overall

8.1

Food

7.2

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • Can I find flights from Illinois to Massachusetts for under $100 on Cheapflights?

    Yes, there are multiple flights from Illinois to Massachusetts for under $100. The cheapest flight booked recently is on Spirit Airlines for just $74, but on average you can expect to pay $149.

  • Are there nonstop flights from Illinois to Massachusetts for under $100 on Cheapflights?

    Cheapflights has at least 15 direct flights from Illinois to Massachusetts under $100. A good price for a nonstop flight from Illinois to Massachusetts is less than $230.

  • Are there last-minute flights available from Illinois to Massachusetts for under $100?

    There are currently 20+ open flights from Illinois to Massachusetts within the next 7 days for less than $100.

  • What days are nonstop flights available from Illinois to Massachusetts?

    Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

  • How many flights depart from Illinois to Massachusetts on average per day?

    On average, you can expect to see 124 flights from Illinois to Massachusetts a day.
    Early Morning (Midnight to 6am) - 2% of flight departures
    Morning (6am - Noon) - 42% of flight departures
    Afternoon (Noon - 6pm) - 29% of flight departures
    Evening (6pm - Midnight) - 27% of flight departures

  • How long is the flight from Illinois to Massachusetts?

    For as low as $74, Spirit Airlines can have you in Massachusetts from Illinois in 2h 18m. Illinois and Massachusetts are separated by a distance of 869 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 Spirit Airlines. According to our data, you can fly for as low as $46. Users have also found prices from $50 and $59 on Frontier and Delta, respectively.

  • What does ORD to BOS mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago O'Hare Intl Airport to Boston Logan Intl Airport flight would often be abbreviated as a ORD to BOS flight. While you’re still figuring out your travel plans, it’s not a bad idea to learn the names and codes of other airports around these areas: Worcester Airport (ORH), Nantucket Memorial Airport (ACK), West Tisbury Martha's Vineyard Airport (MVY), Hyannis Barnstable Airport (HYA), New Bedford Regional Airport (EWB).

  • Can I find deals for flights from Illinois to Massachusetts that include extra baggage allowance?

    The amount of baggage you can bring on your Illinois to Massachusetts flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Illinois to Massachusetts with specific airlines?

    Yes, Cheapflights allows you to browse and filter Illinois to Massachusetts flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Illinois to Massachusetts that allow pets onboard?

    Many airlines flying from Illinois to Massachusetts offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Illinois to Massachusetts?

    Yes, you can often find last-minute deals on Illinois to Massachusetts flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Illinois to Massachusetts flight deals updated?

    The Illinois to Massachusetts flight deals you see on this page were last updated on 10/31.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Illinois to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Fort Lauderdale flights
LaGuardia to Miami flights
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
Newark to Miami flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Los Angeles flights
Dallas/Fort Worth to LaGuardia flights
John F Kennedy Intl to Orlando flights
Los Angeles to Newark flights
LaGuardia to Dallas/Fort Worth flights
Newark to Los Angeles flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Dallas/Fort Worth flights
Newark to Dallas/Fort Worth flights
Los Angeles to Dallas/Fort Worth flights
Dallas/Fort Worth to John F Kennedy Intl flights
San Francisco to John F Kennedy Intl flights
Newark to Orlando flights
Dallas/Fort Worth to Newark flights
Newark to Las Vegas flights
Los Angeles to LaGuardia flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to San Francisco flights
Los Angeles to Seattle flights
LaGuardia to Orlando flights
Los Angeles to Honolulu flights
Miami to John F Kennedy Intl flights
Dallas/Fort Worth to Los Angeles flights
Seattle to Los Angeles flights
O'Hare Intl to Orlando flights
Dallas/Fort Worth to Las Vegas flights
LaGuardia to Hobby flights
LaGuardia to Los Angeles flights
Dallas/Fort Worth to Orlando flights
Newark to Hobby flights
Atlanta to John F Kennedy Intl flights
John F Kennedy Intl to West Palm Beach flights
Hobby to LaGuardia flights
Los Angeles to Las Vegas flights
Seattle to Sky Harbor Intl flights
John F Kennedy Intl to O'Hare Intl flights
Boston to Orlando flights
Miami to LaGuardia flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Fort Lauderdale flights
Baltimore to Dallas/Fort Worth flights

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 2,570,725 searches. Data last updated octubre 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$36Average$91FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$485FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$83Average$122FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$83Average$554FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$136Average$501FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$143Average$536FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$162Average$257FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines