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$77+ 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 7/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Apr 6 — Apr 131
Sun 4/6
Sun 4/13
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 April 1, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$132
(JetBlue Airways)

One-way from

$77
(United Airlines)

Popular in

May

Cheapest in

September

Average price

$282

Good round-trip deal

$231 or less

Good one-way deal

$117 or less
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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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. 11% potential increase in price ($31 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 April 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 April 1, 2025.

This JetBlue Airways deal was found by Cheapflights users on 3/31. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/285:15 pmBOS - ORD
Nonstop3h 12mJetBlue
Fri 5/26:30 pmORD - BOS
Nonstop2h 39mJetBlue
Deal found 3/31$132
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/266:00 amBOS - ORD
Nonstop2h 57mUnited Airlines
Sat 5/312:50 pmORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 3/31$134
This Booking.com deal was found by Cheapflights users on 4/1. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/265:45 pmBOS - ORD
1 stop8h 13mSpirit Airlines
Wed 4/307:47 pmORD - BOS
1 stop13h 35mSpirit Airlines
Deal found 4/1$135
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/82:18 pmORH - ORD
1 stop21h 47mAmerican Airlines
Thu 4/105:10 pmORD - ORH
1 stop19h 15mAmerican Airlines
Deal found 3/31$154
This Southwest deal was found by Cheapflights users on 4/1. 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 5/39:00 amBOS - MDW
Nonstop2h 35mSouthwest
Mon 5/57:20 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 4/1$157
This Priceline deal was found by Cheapflights users on 3/31. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/292:12 pmBOS - ORD
1 stop11h 08mMultiple Airlines
Thu 5/14:15 pmORD - BOS
1 stop7h 50mMultiple Airlines
Deal found 3/31$164
This Delta deal was found by Cheapflights users on 3/31. 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.
Sat 4/267:25 pmBOS - ORD
Nonstop2h 57mDelta
Fri 5/27:20 pmORD - BOS
Nonstop2h 26mDelta
Deal found 3/31$177
This American Airlines deal was found by Cheapflights users on 4/1. 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 4/106:10 amBOS - ORD
Nonstop3h 08mAmerican Airlines
Tue 4/158:05 amORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 4/1$178
This Southwest deal was found by Cheapflights users on 4/1. 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.
Sun 5/46:40 amBOS - ORD
1 stop8h 25mSouthwest
Wed 5/71:50 pmORD - BOS
1 stop6h 15mSouthwest
Deal found 4/1$196
This Frontier deal was found by Cheapflights users on 4/1. 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.
Fri 5/96:00 amBOS - MDW
1 stop7h 24mFrontier
Sun 5/1110:55 amMDW - BOS
1 stop13h 10mFrontier
Deal found 4/1$198
This Delta deal was found by Cheapflights users on 3/31. 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.
Wed 5/74:10 pmORH - ORD
1 stop5h 36mDelta
Mon 5/127:00 amORD - ORH
1 stop7h 05mDelta
Deal found 3/31$212
This CheapOair deal was found by Cheapflights users on 3/31. 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.
Wed 4/166:00 amBOS - ORD
1 stop8h 02mFrontier
Sun 4/209:25 amORD - BOS
1 stop14h 22mFrontier
Deal found 3/31$220

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 1, 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

Mon 4/28

5:15 pm-7:27 pm

Nonstop3h 12m

Chicago O'Hare Intl

Fri 5/2

6:30 pm-10:09 pm

Nonstop2h 39m

$132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 4/26

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Sat 5/3

12:50 pm-4:17 pm

Nonstop2h 27m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 4/26

5:45 pm-12:58 am

1 stop8h 13m

Chicago O'Hare Intl

Wed 4/30

7:47 pm-10:22 am

1 stop13h 35m

$135

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/30

1:49 pm-9:16 am

1 stop20h 27m

Chicago O'Hare Intl

Fri 7/4

4:59 pm-12:43 pm

1 stop18h 44m

$154

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 5/3

9:00 am-10:35 am

Nonstop2h 35m

Chicago Midway

Mon 5/5

7:20 pm-10:35 pm

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/29

2:12 pm-12:20 am

1 stop11h 08m

Chicago O'Hare Intl

Thu 5/1

4:15 pm-1:05 am

1 stop7h 50m

$164

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/10

6:10 am-8:18 am

Nonstop3h 08m

Chicago O'Hare Intl

Tue 4/15

8:05 am-11:30 am

Nonstop2h 25m

$178

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 5/4

6:40 am-2:05 pm

1 stop8h 25m

Chicago O'Hare Intl

Wed 5/7

1:50 pm-9:05 pm

1 stop6h 15m

$196

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/9

6:00 am-12:24 pm

1 stop7h 24m

Chicago Midway

Sun 5/11

10:55 am-1:05 am

1 stop13h 10m

$198

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/23

7:55 pm-9:51 pm

Nonstop2h 56m

Chicago O'Hare Intl

Fri 5/2

7:20 pm-10:46 pm

Nonstop2h 26m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

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 $323). 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 1, 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 1, 2025.

The most flights from USMA to USIL are scheduled on a Tuesday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 1, 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
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,820 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,277 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,898 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
United Airlines
7.4
Good
8,615 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
JetBlue
7.3
Good
2,924 reviews
Alaska Airlines
8.0
Very good
9,820 reviews

Entertainment

7.1

Overall

8.0

Crew

8.5

Boarding

8.2

Comfort

7.9

Food

7.1

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 United Airlines, with whom users have recently found tickets for as low as $77. However, be on the lookout for offers from Spirit Airlines 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 $323). 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 April 1, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$229FlexibilityNo cancel feeOn-time62%
DeltaCheapest$95Average$348FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$509FlexibilityNo cancel feeOn-time69%
FrontierCheapest$99Average$147FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$141Average$475FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$147Average$253FlexibilityNo cancel feeOn-time63%

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