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Illinois

$60+ 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 10/30. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jun 18 — Jun 251
Wed 6/18
Wed 6/25
1 adult, Economy
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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 June 13, 2025.

Round-trip from

$123
(Southwest)

One-way from

$60
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$220

Good round-trip deal

$161 or less

Good one-way deal

$108 or less
From Massachusetts to Illinois
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One-way flight from Massachusetts to Illinois
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Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Price to beat on a round-trip flight from Massachusetts to Illinois.
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Price to beat on a one-way flight from Massachusetts to Illinois.
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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 June 13, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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 8/75:15 amBOS - MDW
Nonstop2h 30mSouthwest
Sun 8/1010:00 amMDW - BOS
Nonstop2h 25mSouthwest
Deal found 6/11$123
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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.
Wed 7/25:45 amBOS - ORD
1 stop13h 59mSpirit Airlines
Wed 7/165:05 amORD - BOS
1 stop13h 29mSpirit Airlines
Deal found 6/10$124
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Mon 8/187:45 amBOS - ORD
Nonstop2h 58mUnited Airlines
Thu 8/216:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 6/10$125
This American Airlines deal was found by Cheapflights users on 6/12. 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 10/235:00 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Mon 10/278:30 pmORD - BOS
Nonstop2h 44mAmerican Airlines
Deal found 6/12$126
This JetBlue deal was found by Cheapflights users on 6/12. 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 8/216:00 amBOS - ORD
Nonstop2h 55mJetBlue
Mon 8/258:40 amORD - BOS
Nonstop2h 25mJetBlue
Deal found 6/12$131
This Southwest deal was found by Cheapflights users on 6/12. 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.
Tue 7/157:00 amBOS - ORD
1 stop5h 50mSouthwest
Wed 7/164:00 pmORD - BOS
1 stop6h 55mSouthwest
Deal found 6/12$142
This Delta deal was found by Cheapflights users on 6/12. 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.
Thu 11/2711:00 amBOS - ORD
Nonstop2h 52mDelta
Tue 12/210:10 amORD - BOS
Nonstop2h 32mDelta
Deal found 6/12$158
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Sat 7/123:29 pmORH - ORD
2 stops9h 28mAmerican Airlines
Sat 7/195:00 amORD - ORH
1 stop9h 04mAmerican Airlines
Deal found 6/11$164
This FlightHub deal was found by Cheapflights users on 6/12. 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 9/179:15 amBDL - STL
1 stop23h 34mSpirit Airlines
Sun 9/218:44 amSTL - BDL
1 stop22h 26mSpirit Airlines
Deal found 6/12$176
This Mytrip deal was found by Cheapflights users on 6/11. 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 8/111:42 amBOS - RFD
1 stop23h 31mMultiple Airlines
Sun 8/39:21 amRFD - BOS
1 stop5h 22mMultiple Airlines
Deal found 6/11$206
This Mytrip deal was found by Cheapflights users on 6/11. 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.
Sun 6/2911:31 amBOS - MDW
1 stop20h 44mAllegiant Air
Wed 7/29:03 amMDW - BOS
1 stop24h 38mAllegiant Air
Deal found 6/11$211
This Delta deal was found by Cheapflights users on 6/11. 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 7/223:48 pmORH - ORD
1 stop6h 01mDelta
Thu 7/247:05 amORD - ORH
1 stop6h 59mDelta
Deal found 6/11$212

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 June 13, 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 - MDW

BOSMDW

Boston Logan Intl

Thu 8/7

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

Sun 8/10

10:00 am-1:25 pm

Nonstop2h 25m

$123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 7/2

5:45 am-6:44 pm

1 stop13h 59m

Chicago O'Hare Intl

Wed 7/16

5:05 am-7:34 pm

1 stop13h 29m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 8/18

7:45 am-9:43 am

Nonstop2h 58m

Chicago O'Hare Intl

Thu 8/21

6:30 am-9:56 am

Nonstop2h 26m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 10/23

5:00 am-6:58 am

Nonstop2h 58m

Chicago O'Hare Intl

Mon 10/27

8:30 pm-12:14 am

Nonstop2h 44m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/21

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Mon 8/25

8:40 am-12:05 pm

Nonstop2h 25m

$131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 7/15

7:00 am-11:50 am

1 stop5h 50m

Chicago O'Hare Intl

Wed 7/16

4:00 pm-11:55 pm

1 stop6h 55m

$142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 11/27

11:00 am-12:52 pm

Nonstop2h 52m

Chicago O'Hare Intl

Tue 12/2

10:10 am-1:42 pm

Nonstop2h 32m

$158

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 7/12

3:29 pm-11:57 pm

2 stops9h 28m

Chicago O'Hare Intl

Sat 7/19

5:00 am-3:04 pm

1 stop9h 04m

$164

HartfordSt. Louis

BDL - STL

BDLSTL

Hartford Bradley Intl

Fri 8/8

6:20 am-9:52 am

1 stop4h 32m

Lambert-St Louis

Sun 8/17

2:27 pm-11:06 pm

1 stop7h 39m

$187

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

Fri 8/1

11:42 am-10:13 am

1 stop23h 31m

Chicago Greater Rockford

Sun 8/3

9:21 am-3:43 pm

1 stop5h 22m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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.

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 June 13, 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 June 13, 2025.

The most flights from USMA to USIL are scheduled on a Thursday (78 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 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 June 13, 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
10,000 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,923 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Food

7.1

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Overall

8.0

Crew

8.5

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 Spirit Airlines, with whom users have recently found tickets for as low as $60. 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, 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

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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 2,558,603 searches. Data last updated June 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$103FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$79Average$203FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$367FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$449FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$134FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$127Average$304FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$136Average$432FlexibilityNo cancel feeOn-time71%

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