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$60+ Cheap flights from Massachusetts to Chicago (CHI)

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 — CHI
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
1 adult, Economy
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Cheap flight deals from Massachusetts to Chicago

Keep the following information in mind while searching for Massachusetts to Chicago flight deals. Data was last updated junio 12, 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 Chicago (CHI)
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One-way flight from Massachusetts to Chicago (CHI)
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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 Chicago (CHI).
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Price to beat on a one-way flight from Massachusetts to Chicago (CHI).
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Find flight deals from Massachusetts to Chicago

Cheapest flights from Massachusetts to Chicago
Explore the most affordable flight options available from Massachusetts to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on junio 12, 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.
jue. 8/75:15 amBOS - MDW
Nonstop2h 30mSouthwest
dom. 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.
mié. 7/25:45 amBOS - ORD
1 stop13h 59mSpirit Airlines
mié. 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.
mar. 8/56:07 amBOS - ORD
Nonstop2h 58mUnited Airlines
vie. 8/87:49 pmORD - BOS
Nonstop2h 27mUnited 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.
jue. 10/235:00 amBOS - ORD
Nonstop2h 58mAmerican Airlines
lun. 10/278:30 pmORD - BOS
Nonstop2h 44mAmerican Airlines
Deal found 6/12$126
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.
mar. 7/225:45 amBOS - ORD
1 stop7h 05mSouthwest
vie. 7/254:00 pmORD - BOS
1 stop7h 05mSouthwest
Deal found 6/12$142
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 9/184:23 pmORH - ORD
1 stop7h 16mAmerican Airlines
lun. 9/229:37 pmORD - ORH
1 stop17h 22mAmerican Airlines
Deal found 6/10$154
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/277:55 pmBOS - ORD
Nonstop2h 59mDelta
mar. 9/27:00 amORD - BOS
Nonstop2h 30mDelta
Deal found 6/10$158
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/106:00 amBOS - ORD
Nonstop2h 55mJetBlue
lun. 7/148:40 amORD - BOS
Nonstop2h 24mJetBlue
Deal found 6/11$176
This Mytrip deal was found by Cheapflights users on 6/9. 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.
jue. 8/711:31 amBOS - MDW
1 stop20h 42mAllegiant Air
lun. 8/112:46 pmMDW - BOS
1 stop17h 29mAllegiant Air
Deal found 6/9$201
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.
vie. 8/111:42 amBOS - RFD
1 stop23h 31mMultiple Airlines
dom. 8/39:21 amRFD - BOS
1 stop5h 22mMultiple Airlines
Deal found 6/11$206
This Delta deal was found by Cheapflights users on 6/9. 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.
vie. 7/43:51 pmORH - ORD
1 stop5h 51mDelta
mié. 7/99:25 amORD - ORH
1 stop4h 39mDelta
Deal found 6/9$212
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/156:00 amBDL - ORD
Nonstop2h 48mUnited Airlines
mié. 7/165:56 pmORD - BDL
1 stop5h 03mUnited Airlines
Deal found 6/12$227

Cheapflights Fare Finder

Customize your flight search to find flights from Massachusetts to Chicago 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 junio 12, 2025.
Use the filters below to find and compare flights from Massachusetts to Chicago that are best for you.

Fly from

Massachusetts

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 8/7

5:15 am-6:45 am

Nonstop2h 30m

Chicago Midway

dom. 8/10

10:00 am-1:25 pm

Nonstop2h 25m

$123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 7/2

5:45 am-6:44 pm

1 stop13h 59m

Chicago O'Hare Intl

mié. 7/16

5:05 am-7:34 pm

1 stop13h 29m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 8/5

6:07 am-8:05 am

Nonstop2h 58m

Chicago O'Hare Intl

vie. 8/8

7:49 pm-11:16 pm

Nonstop2h 27m

$125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 10/23

5:00 am-6:58 am

Nonstop2h 58m

Chicago O'Hare Intl

lun. 10/27

8:30 pm-12:14 am

Nonstop2h 44m

$126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 7/8

6:00 am-7:55 am

Nonstop2h 55m

Chicago O'Hare Intl

jue. 7/10

4:27 pm-8:00 pm

Nonstop2h 33m

$137

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 7/22

5:45 am-11:50 am

1 stop7h 05m

Chicago O'Hare Intl

vie. 7/25

4:00 pm-12:05 am

1 stop7h 05m

$142

WorcesterChicago

ORH - ORD

ORHORD

Worcester

jue. 9/18

4:23 pm-10:39 pm

1 stop7h 16m

Chicago O'Hare Intl

lun. 9/22

9:37 pm-3:59 pm

1 stop17h 22m

$154

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 8/27

7:55 pm-9:54 pm

Nonstop2h 59m

Chicago O'Hare Intl

mar. 9/2

7:00 am-10:30 am

Nonstop2h 30m

$158

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 8/7

11:31 am-7:13 am

1 stop20h 42m

Chicago Midway

lun. 8/11

2:46 pm-9:15 am

1 stop17h 29m

$201

BostonChicago

BOS - RFD

BOSRFD

Boston Logan Intl

vie. 8/1

11:42 am-10:13 am

1 stop23h 31m

Chicago Greater Rockford

dom. 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 Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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 Chicago

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

Currently, August is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $245). Flying from Massachusetts to Chicago 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 CHI?

Find hourly flight availability from Massachusetts to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated junio 12, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Massachusetts to Chicago as you normally would.

Weekly flight availability from Massachusetts to Chicago

Explore weekly flight availability from Massachusetts to Chicago. 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 junio 12, 2025.

The most flights from USMA to CHI are scheduled on a Thursday (84 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago 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 Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, 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 Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated junio 12, 2025.
Read through reviews of airlines operating flights from Massachusetts to Chicago, such as Alaska Airlines, Southwest and Delta. 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

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

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 Chicago. 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 Chicago one-way?

    To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $60. Southwest flights start at $62 while deals on United Airlines start at $63 one-way.

  • What are the most popular routes from Massachusetts to Chicago?

    While some choose either Boston Logan Intl - Chicago Midway or Hartford Bradley Intl - Chicago O'Hare Intl, Boston Logan Intl - Chicago O'Hare Intl is the most popular route from Massachusetts to Chicago.

  • What are the most reliable airlines from Massachusetts to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Massachusetts to Chicago on time: Japan Airlines (92%), Avianca (90%), Icelandair (88%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $1,017, our data indicates the cheapest price to be $62. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $112.

  • Can I find deals for flights from Massachusetts to Chicago that include hotel bookings?

    Yes. In addition to deals on Massachusetts to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Massachusetts to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Massachusetts to Chicago.

  • Can I find deals for business class flights from Massachusetts to Chicago?

    Yes. Cheapflights offers flight deals from Massachusetts to Chicago 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 Chicago?

    Currently, August is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $245). Flying from Massachusetts to Chicago 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

Traveling to a place near Massachusetts?

Book flights to Massachusetts if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
Chesterton

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Alternative routes for Massachusetts to Chicago

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 Chicago

Discover the top 7 airlines that operate flights from Massachusetts to Chicago. 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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$103FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$79Average$203FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$312FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$97Average$234FlexibilityNo cancel feeOn-time69%
FrontierCheapest$100Average$134FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$127Average$304FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$136Average$255FlexibilityNo cancel feeOn-time71%

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