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$63+ 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 2/17. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — ORD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This JetBlue deal was found by Cheapflights users on 12/15. 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 12/254:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Mon 12/297:41 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 12/15$132
This Expedia deal was found by Cheapflights users on 12/15. 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.
Tue 12/2312:08 pmBOS - ORD
1 stop23h 10mMultiple Airlines
Wed 1/77:45 amORD - BOS
Nonstop2h 25mMultiple Airlines
Deal found 12/15$156
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/186:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Fri 12/197:45 amORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 12/15$157
This Expedia deal was found by Cheapflights users on 12/15. 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.
Tue 12/2312:08 pmBOS - ORD
1 stop23h 10mFrontier
Wed 1/74:49 pmORD - BOS
1 stop7h 30mFrontier
Deal found 12/15$162
This Priceline deal was found by Cheapflights users on 12/16. 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 12/2311:02 amBOS - ORD
1 stop8h 50mMultiple Airlines
Thu 12/257:41 pmORD - BOS
Nonstop2h 29mMultiple Airlines
Deal found 12/16$166
This Delta deal was found by Cheapflights users on 12/15. 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 12/244:47 pmBDL - MDW
1 stop6h 35mDelta
Thu 1/16:00 amMDW - BDL
1 stop6h 14mDelta
Deal found 12/15$177
This Delta deal was found by Cheapflights users on 12/16. 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 12/255:30 amBDL - ORD
1 stop4h 31mDelta
Thu 12/255:31 pmORD - BDL
1 stop5h 05mDelta
Deal found 12/16$177
This American Airlines deal was found by Cheapflights users on 12/17. 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.
Wed 12/315:40 pmBOS - ORD
Nonstop3h 12mAmerican Airlines
Fri 1/235:25 pmORD - BOS
Nonstop2h 20mAmerican Airlines
Deal found 12/17$177
This American Airlines deal was found by Cheapflights users on 12/14. 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.
Wed 12/176:00 amBOS - ORD
Nonstop3h 17mAmerican Airlines
Fri 12/197:25 amORD - BOS
Nonstop2h 33mAmerican Airlines
Deal found 12/14$187
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/296:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Sun 1/47:45 amORD - BOS
Nonstop2h 23mUnited Airlines
Deal found 12/16$189
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/206:23 pmBOS - ORD
Nonstop3h 02mUnited Airlines
Thu 12/251:55 pmORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 12/17$192
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/186:01 amBOS - ORD
Nonstop3h 04mUnited Airlines
Sun 1/49:12 pmORD - BOS
Nonstop2h 33mUnited Airlines
Deal found 12/15$196

Find flight deals from Massachusetts to Illinois

Keep the following information in mind while searching for Massachusetts to Illinois flight deals. Data was last updated December 18, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$124
(Kiwi.com)

One-way from

$63
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$253

Good round-trip deal

$229 or less

Good one-way deal

$138 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 ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 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

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 December 18, 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

Wed 2/25

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Fri 2/27

7:40 pm-10:55 pm

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/21

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Sat 3/7

10:00 am-1:23 pm

Nonstop2h 23m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 2/26

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 3/2

11:05 am-2:30 pm

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/23

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Sun 1/25

7:05 am-10:40 am

Nonstop2h 35m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 2/7

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Sat 2/14

6:10 pm-9:25 pm

Nonstop2h 15m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/14

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/18

7:45 am-11:10 am

Nonstop2h 25m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/1

6:01 am-8:05 am

Nonstop3h 04m

Chicago O'Hare Intl

Fri 1/2

9:12 pm-12:45 am

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 1/24

7:30 am-9:41 am

Nonstop3h 11m

Chicago O'Hare Intl

Sun 1/25

7:05 am-10:40 am

Nonstop2h 35m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/24

7:00 am-9:10 am

Nonstop3h 10m

Chicago O'Hare Intl

Fri 3/6

10:00 am-1:23 pm

Nonstop2h 23m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 1/7

3:35 pm-5:43 pm

Nonstop3h 08m

Chicago O'Hare Intl

Fri 1/16

7:45 am-11:10 am

Nonstop2h 25m

$137

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

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, April is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $89). Flying from Massachusetts to Illinois in January is currently the most expensive (average of $122). 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 December 18, 2025.

A simple way to save on the total cost of your ticket is to fly from Massachusetts to Illinois in the evening. If you’re flexible enough to do this you can expect to save up to 61% on your trip compared to booking a flight in the afternoon.

What is the cheapest day to fly from Massachusetts to Illinois?

Use this chart to determine the cheapest time to fly round-trip from Massachusetts to Illinois. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Massachusetts to Illinois flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

How much does it cost to fly round-trip from Massachusetts to Illinois?

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 December 18, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Massachusetts to Illinois have to say. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,897 reviews
Southwest
7.9
Good
4,250 reviews

Entertainment

7.5

Food

7.0

Crew

8.6

Boarding

8.1

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Massachusetts to Illinois?

    Airlines like Southwest, JetBlue, and United Airlines fly from Massachusetts to Illinois in about 2h 50m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 857 mi. Most flights are nonstop.

  • 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 $46. However, be on the lookout for offers from Frontier 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, April is the cheapest month in which you can book a flight from Massachusetts to Illinois (average of $89). Flying from Massachusetts to Illinois in January is currently the most expensive (average of $122). 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 6 airlines flying from Massachusetts to Illinois

Discover the top 6 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$75Average$187FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$308FlexibilityNo cancel feeOn-time65%
DeltaCheapest$112Average$289FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$117Average$234FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$123Average$436FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$128Average$424FlexibilityNo cancel feeOn-time71%

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