HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Illinois

$59+ Cheap flights from Massachusetts to Illinois

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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Apr 27 — May 41
Sun 4/27
Sun 5/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Massachusetts to Illinois 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.

Cheap flight deals from Massachusetts to Illinois

Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated April 22, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$127
(Southwest)

One-way from

$59
(Southwest)

Popular in

May

Cheapest in

September

Average price

$275

Good round-trip deal

$174 or less

Good one-way deal

$110 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Massachusetts to Illinois
Search Deals
One-way flight from Massachusetts to Illinois
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Massachusetts to Illinois.
Search Deals
Price to beat on a one-way flight from Massachusetts to Illinois.
Search Deals

Find flight deals from Massachusetts to Illinois

Cheapest flights from Massachusetts to Illinois
Explore the most affordable flight options available from Massachusetts to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 22, 2025.

This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 5/313:00 pmBOS - MDW
1 stop7h 50mSouthwest
Thu 7/36:00 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 4/21$127
This Cheapflightsfares deal was found by Cheapflights users on 4/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/95:42 pmBOS - ORD
1 stop6h 47mSpirit Airlines
Wed 5/1412:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Deal found 4/21$129
This Southwest deal was found by Cheapflights users on 4/21. 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.
Sat 6/76:45 amBOS - ORD
1 stop9h 15mSouthwest
Wed 6/114:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 4/21$136
This United Airlines deal was found by Cheapflights users on 4/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/57:45 amBOS - ORD
Nonstop2h 58mUnited Airlines
Mon 6/96:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 4/21$137
This American Airlines deal was found by Cheapflights users on 4/22. 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.
Thu 5/16:10 amBOS - ORD
Nonstop3h 08mAmerican Airlines
Mon 5/54:40 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Deal found 4/22$147
This JetBlue deal was found by Cheapflights users on 4/21. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/56:00 amBOS - ORD
Nonstop3h 00mJetBlue
Tue 6/107:31 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 4/21$152
This FlightHub deal was found by Cheapflights users on 4/21. 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.
Wed 5/143:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Sat 5/174:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Deal found 4/21$153
This Delta deal was found by Cheapflights users on 4/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/78:20 pmBOS - ORD
Nonstop2h 54mDelta
Sun 5/117:00 amORD - BOS
Nonstop2h 25mDelta
Deal found 4/20$180
This Frontier deal was found by Cheapflights users on 4/22. 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.
Wed 5/2810:45 amBOS - MDW
1 stop12h 51mFrontier
Sun 6/19:12 pmMDW - BOS
1 stop10h 23mFrontier
Deal found 4/22$188
This Frontier deal was found by Cheapflights users on 4/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/298:47 amBOS - ORD
1 stop9h 21mFrontier
Sun 6/15:14 pmORD - BOS
1 stop14h 21mFrontier
Deal found 4/21$200
This Mytrip deal was found by Cheapflights users on 4/21. 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.
Thu 7/311:31 amBOS - MDW
1 stop20h 42mAllegiant Air
Mon 7/72:54 pmMDW - BOS
1 stop17h 21mAllegiant Air
Deal found 4/21$225
This Mytrip deal was found by Cheapflights users on 4/22. 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 6/1211:31 amBOS - MDW
1 stop20h 44mMultiple Airlines
Mon 6/168:36 pmMDW - BOS
3 stops35h 27mMultiple Airlines
Deal found 4/22$249

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Illinois 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 22, 2025.
Use the filters below to find and compare flights from Massachusetts to Illinois that are best for you.

Fly from

Massachusetts

Fly to

Illinois

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/20

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Wed 5/21

12:41 pm-11:29 pm

1 stop9h 48m

$118

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 5/31

3:00 pm-9:50 pm

1 stop7h 50m

Chicago Midway

Thu 7/3

6:00 am-9:15 am

Nonstop2h 15m

$127

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/7

6:45 am-3:00 pm

1 stop9h 15m

Chicago O'Hare Intl

Wed 6/11

4:00 pm-11:55 pm

1 stop6h 55m

$136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 5/6

7:45 am-9:42 am

Nonstop2h 57m

Chicago O'Hare Intl

Thu 5/8

1:55 pm-5:19 pm

Nonstop2h 24m

$138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/30

5:00 am-7:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Fri 5/2

4:49 pm-8:09 pm

Nonstop2h 20m

$147

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/5

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 6/14

9:40 am-1:09 pm

Nonstop2h 29m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/14

3:49 pm-11:04 pm

1 stop8h 15m

Chicago O'Hare Intl

Sat 5/17

4:15 pm-12:44 am

1 stop7h 29m

$153

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/2

8:05 pm-10:05 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 7/8

10:10 am-1:40 pm

Nonstop2h 30m

$177

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 5/28

10:45 am-10:36 pm

1 stop12h 51m

Chicago Midway

Sun 6/1

9:12 pm-8:35 am

1 stop10h 23m

$188

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 5/10

8:00 am-11:32 pm

1 stop16h 32m

Chicago O'Hare Intl

Mon 5/12

4:15 pm-12:44 am

1 stop7h 29m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Massachusetts to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Massachusetts 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 Massachusetts to Illinois

What is the cheapest month to book a flight from Massachusetts to Illinois?

Currently, August is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $245). Flying from Massachusetts to Illinois in March is currently the most expensive (average of $321). 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 MA to IL?

Find hourly flight availability from Massachusetts to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 22, 2025.

When flying from Massachusetts to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Massachusetts to Illinois

Explore weekly flight availability from Massachusetts to Illinois. 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 22, 2025.

The most flights from USMA to USIL are scheduled on a Monday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (15 on average).

Rainfall in Illinois by month

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

In terms of precipitation, rainfall in Illinois ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Illinois when rainfall is around 1.7 in.

Temperature in Illinois by month

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

If weather is an important factor for your trip to Illinois, 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 23.0 F).

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated April 22, 2025.
To help decide which airline to fly from Massachusetts to Illinois, see what other customers have to say about Alaska Airlines, Southwest and Delta. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

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
9,911 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

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
4,287 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

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
7,920 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

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
8,683 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
9,911 reviews

Entertainment

7.1

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.5

Comfort

7.9

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 Massachusetts to Illinois. 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 Massachusetts to Illinois one-way?

    The cheapest airline one-way is Southwest, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from JetBlue and United Airlines, as they are both options that can get you from Massachusetts to Illinois for a low price.

  • Can I find deals for flights from Massachusetts to Illinois that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Illinois.

  • Can I find deals for business class flights from Massachusetts to Illinois?

    Yes. Cheapflights offers flight deals from Massachusetts to Illinois 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 Massachusetts to Illinois?

    Currently, August is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $245). Flying from Massachusetts to Illinois in March is currently the most expensive (average of $321). 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 Massachusetts to Illinois

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

Top 7 airlines flying from Massachusetts to Illinois

Discover the top 7 airlines that operate flights from Massachusetts to Illinois. 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 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$220FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$376FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$493FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$151FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$139Average$318FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$139Average$483FlexibilityNo cancel feeOn-time71%

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.