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$55+ 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 5/1. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$120
(CheapOair)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

September

Average price

$256

Good round-trip deal

$225 or less

Good one-way deal

$123 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. 14% potential increase in price ($40 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This CheapOair deal was found by Cheapflights users on 2/19. 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.
Thu 4/312:04 pmBDL - STL
1 stop12h 42mFrontier
Mon 4/74:57 pmSTL - BDL
1 stop24h 10mFrontier
Deal found 2/19$120
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/242:12 pmBOS - ORD
3 stops18h 52mSpirit Airlines
Mon 4/2810:19 amORD - BOS
2 stops27h 36mSpirit Airlines
Deal found 2/19$151
This Frontier deal was found by Cheapflights users on 2/19. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/215:10 amBOS - MDW
1 stop7h 24mFrontier
Mon 3/248:27 pmMDW - BOS
1 stop13h 06mFrontier
Deal found 2/19$152
This Frontier deal was found by Cheapflights users on 2/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/216:00 amBOS - ORD
1 stop12h 26mFrontier
Mon 3/245:47 pmORD - BOS
1 stop5h 57mFrontier
Deal found 2/20$152
This FlightHub deal was found by Cheapflights users on 2/19. 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.
Thu 4/108:31 pmBOS - ORD
1 stop12h 33mMultiple Airlines
Mon 4/148:55 amORD - BOS
1 stop14h 52mMultiple Airlines
Deal found 2/19$153
This Southwest deal was found by Cheapflights users on 2/20. 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.
Thu 2/276:50 amBOS - MDW
Nonstop2h 55mSouthwest
Tue 3/46:25 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 2/20$157
This Delta deal was found by Cheapflights users on 2/20. 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.
Thu 2/277:15 amBOS - ORD
Nonstop3h 06mDelta
Fri 2/287:10 amORD - BOS
Nonstop2h 33mDelta
Deal found 2/20$157
This CheapOair deal was found by Cheapflights users on 2/19. 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.
Sat 5/109:53 amBDL - STL
1 stop15h 13mMultiple Airlines
Tue 5/137:37 pmSTL - BDL
1 stop19h 24mMultiple Airlines
Deal found 2/19$158
This American Airlines deal was found by Cheapflights users on 2/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/48:59 pmBOS - ORD
Nonstop2h 58mAmerican Airlines
Mon 4/76:35 pmORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 2/19$161
This United Airlines deal was found by Cheapflights users on 2/19. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/85:30 amBOS - ORD
1 stop5h 08mUnited Airlines
Wed 3/124:05 pmORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 2/19$163
This JetBlue deal was found by Cheapflights users on 2/20. 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 3/75:37 amBOS - ORD
1 stop6h 22mJetBlue
Thu 3/131:15 pmORD - BOS
Nonstop2h 24mJetBlue
Deal found 2/20$177
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Mon 3/312:10 pmORH - ORD
1 stop21h 41mAmerican Airlines
Fri 4/45:10 pmORD - ORH
1 stop18h 58mAmerican Airlines
Deal found 2/20$214

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 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Massachusetts

Fly to

Illinois

Route

Depart

Return

Price

HartfordSt. Louis

BDL - STL

BDLSTL

Hartford Bradley Intl

Thu 4/3

12:04 pm-11:46 pm

1 stop12h 42m

Lambert-St Louis

Mon 4/7

4:57 pm-6:07 pm

1 stop24h 10m

$120

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/24

2:12 pm-8:04 am

3 stops18h 52m

Chicago O'Hare Intl

Mon 4/28

10:19 am-2:55 pm

2 stops27h 36m

$151

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 3/21

5:10 am-11:34 am

1 stop7h 24m

Chicago Midway

Mon 3/24

8:27 pm-10:33 am

1 stop13h 06m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/21

6:00 am-5:26 pm

1 stop12h 26m

Chicago O'Hare Intl

Mon 3/24

5:47 pm-12:44 am

1 stop5h 57m

$152

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/10

8:31 pm-8:04 am

1 stop12h 33m

Chicago O'Hare Intl

Mon 4/14

8:55 am-12:47 am

1 stop14h 52m

$153

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 2/27

6:50 am-8:45 am

Nonstop2h 55m

Chicago Midway

Tue 3/4

6:25 pm-9:40 pm

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 3/4

7:15 am-9:21 am

Nonstop3h 06m

Chicago O'Hare Intl

Wed 3/5

7:10 am-10:43 am

Nonstop2h 33m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 3/15

7:30 am-9:34 am

Nonstop3h 04m

Chicago O'Hare Intl

Tue 3/18

7:30 am-10:49 am

Nonstop2h 19m

$158

HartfordSt. Louis

BDL - STL

BDLSTL

Hartford Bradley Intl

Sat 5/10

9:53 am-12:06 am

1 stop15h 13m

Lambert-St Louis

Tue 5/13

7:37 pm-4:01 pm

1 stop19h 24m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

8:59 pm-10:57 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 4/7

6:35 pm-10:06 pm

Nonstop2h 31m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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, 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 February 20, 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 February 20, 2025.

The most flights from USMA to USIL are scheduled on a Thursday (54 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 February 20, 2025.
To help decide which airline to fly from Massachusetts to Illinois, see what other customers have to say about Southwest, Alaska Airlines 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.
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Food

7.1

Entertainment

7.6

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Food

7.1

Entertainment

7.6

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Food

7.1

Entertainment

7.6

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Food

7.1

Entertainment

7.6

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Qatar Airways
7.4
Good
3,609 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Food

7.1

Entertainment

7.6

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Boarding

8.2

Food

7.1

Entertainment

7.6

Comfort

8.1

Overall

8.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $55. However, be on the lookout for offers from Spirit Airlines and Southwest, 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$97Average$355FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$146FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$480FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$517FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$151Average$246FlexibilityNo cancel feeOn-time63%
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