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$74+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Massachusetts to Illinois

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Illinois (USIL). 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 November 20, 2024.

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 November 20, 2024.

This CheapOair deal was found by Cheapflights users on 11/19. 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 12/116:00 amBOS - MDW
1 stop6h 42mFrontier
Fri 12/137:00 amMDW - BOS
1 stop16h 30mFrontier
Deal found 11/19$124
This CheapOair deal was found by Cheapflights users on 11/18. 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 12/116:00 amBOS - ORD
1 stop27h 24mFrontier
Sun 12/159:35 amORD - BOS
1 stop13h 55mFrontier
Deal found 11/18$124
This Kiwi.com deal was found by Cheapflights users on 11/19. 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.
Tue 12/105:00 amBOS - ORD
1 stop12h 06mMultiple Airlines
Fri 12/1310:59 amORD - BOS
1 stop12h 31mMultiple Airlines
Deal found 11/19$129
This Expedia deal was found by Cheapflights users on 11/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/75:00 amBOS - ORD
1 stop12h 06mSpirit Airlines
Tue 12/109:58 amORD - BOS
1 stop13h 40mSpirit Airlines
Deal found 11/19$134
This JetBlue deal was found by Cheapflights users on 11/20. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/66:00 amBOS - ORD
Nonstop3h 06mJetBlue
Wed 12/118:51 amORD - BOS
Nonstop2h 22mJetBlue
Deal found 11/20$157
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/47:00 amBOS - MDW
Nonstop2h 45mSouthwest
Fri 12/66:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 11/20$158
This FlightHub deal was found by Cheapflights users on 11/19. 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.
Mon 12/1611:31 amBDL - STL
1 stop13h 02mFrontier
Sun 1/125:05 pmSTL - BDL
1 stop16h 32mFrontier
Deal found 11/19$168
This American Airlines deal was found by Cheapflights users on 11/20. 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 12/136:47 amBOS - ORD
Nonstop3h 05mAmerican Airlines
Thu 1/27:19 amORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 11/20$182
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/187:38 pmBOS - ORD
1 stop4h 42mUnited Airlines
Wed 12/259:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 11/20$183
This Mytrip deal was found by Cheapflights users on 11/18. 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 12/56:00 amBDL - ORD
2 stops18h 07mSpirit Airlines
Tue 12/105:00 amORD - BDL
1 stop16h 02mSpirit Airlines
Deal found 11/18$222
This FlightHub deal was found by Cheapflights users on 11/19. 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 12/46:00 amBOS - STL
1 stop18h 24mMultiple Airlines
Sun 12/84:26 pmSTL - BOS
1 stop15h 48mMultiple Airlines
Deal found 11/19$223
This Delta deal was found by Cheapflights users on 11/19. 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.
Sun 12/297:40 pmBOS - ORD
Nonstop3h 01mDelta
Fri 1/37:35 amORD - BOS
Nonstop2h 28mDelta
Deal found 11/19$223

Find flights from Massachusetts to Illinois within your budget

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 2,629,791 searches. Data last updated November 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/11

6:00 am-11:42 am

1 stop6h 42m

Chicago Midway

Fri 12/13

7:00 am-12:30 am

1 stop16h 30m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 12/11

6:00 am-8:24 am

1 stop27h 24m

Chicago O'Hare Intl

Sun 12/15

9:35 am-12:30 am

1 stop13h 55m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/10

5:00 am-4:06 pm

1 stop12h 06m

Chicago O'Hare Intl

Tue 12/17

5:38 pm-12:35 am

1 stop5h 57m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 12/7

5:00 am-4:06 pm

1 stop12h 06m

Chicago O'Hare Intl

Tue 12/10

9:58 am-12:38 am

1 stop13h 40m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 12/6

6:00 am-8:06 am

Nonstop3h 06m

Chicago O'Hare Intl

Wed 12/11

8:51 am-12:13 pm

Nonstop2h 22m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 12/4

7:00 am-8:45 am

Nonstop2h 45m

Chicago Midway

Fri 12/6

6:25 pm-9:35 pm

Nonstop2h 10m

$158

HartfordSt. Louis

BDL - STL

BDLSTL

Hartford Bradley Intl

Tue 1/7

6:00 am-3:21 pm

1 stop10h 21m

Lambert-St Louis

Sat 1/11

5:05 pm-9:52 am

1 stop15h 47m

$167

HartfordSt. Louis

BDL - STL

BDLSTL

Hartford Bradley Intl

Mon 12/16

11:31 am-11:33 pm

1 stop13h 02m

Lambert-St Louis

Sun 1/12

5:05 pm-10:37 am

1 stop16h 32m

$168

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/1

6:02 am-8:05 am

Nonstop3h 03m

Chicago O'Hare Intl

Mon 2/3

9:10 am-3:41 pm

1 stop5h 31m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 12/31

6:45 am-8:49 am

Nonstop3h 04m

Chicago O'Hare Intl

Sun 1/5

8:30 pm-12:15 am

Nonstop2h 45m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 60 results
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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.

Travel insights for flights from Massachusetts to Illinois

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

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

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $232). Flying from Massachusetts to Illinois in June is currently the most expensive (average of $308). 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 November 20, 2024.

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 November 20, 2024.

The most flights from USMA to USIL are scheduled on a Monday (47 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 November 20, 2024.
To help decide which airline to fly from Massachusetts to Illinois, see what other customers have to say about American Airlines, Frontier and Spirit Airlines. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

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

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

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

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

Reviews

1 / 10

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

United Airlines
7.4
Good
9,171 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Overall

8.1

Food

7.2

Boarding

8.2

Crew

8.7

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 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 Frontier, with whom users have recently found tickets for as low as $74. However, be on the lookout for offers from Southwest and JetBlue, 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, September is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $232). Flying from Massachusetts to Illinois in June is currently the most expensive (average of $308). 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 Massachusetts to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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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 2,629,791 searches. Data last updated November 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$360FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$134FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$135Average$485FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$145Average$234FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$147Average$438FlexibilityNo cancel feeOn-time69%
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