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$74+ 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 12/25. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
nov. 25 — dic. 21
lun. 11/25
lun. 12/2
1 adult, Economy
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Cheap flight deals from Massachusetts to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Massachusetts (USMA) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated noviembre 20, 2024.

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 noviembre 20, 2024.

This CheapOair deal was found by Cheapflights users on 11/19. 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.
mié. 12/116:00 amBOS - MDW
1 stop6h 42mFrontier
vie. 12/137:00 amMDW - BOS
1 stop16h 30mFrontier
Deal found 11/19$124
This CheapOair deal was found by Cheapflights users on 11/18. 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.
mié. 12/116:00 amBOS - ORD
1 stop27h 24mFrontier
dom. 12/159:35 amORD - BOS
1 stop13h 55mFrontier
Deal found 11/18$124
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/105:00 amBOS - ORD
1 stop12h 06mMultiple Airlines
vie. 12/1310:59 amORD - BOS
1 stop12h 31mMultiple Airlines
Deal found 11/19$129
This Expedia deal was found by Cheapflights users on 11/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/75:00 amBOS - ORD
1 stop12h 06mSpirit Airlines
mar. 12/109:58 amORD - BOS
1 stop13h 40mSpirit Airlines
Deal found 11/19$134
This JetBlue deal was found by Cheapflights users on 11/20. 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.
vie. 12/66:00 amBOS - ORD
Nonstop3h 06mJetBlue
mié. 12/118:51 amORD - BOS
Nonstop2h 22mJetBlue
Deal found 11/20$157
This Southwest deal was found by Cheapflights users on 11/20. 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.
mié. 12/47:00 amBOS - MDW
Nonstop2h 45mSouthwest
vie. 12/66:25 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 11/20$158
This American Airlines deal was found by Cheapflights users on 11/20. 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.
vie. 12/136:47 amBOS - ORD
Nonstop3h 05mAmerican Airlines
jue. 1/27:19 amORD - BOS
Nonstop2h 31mAmerican Airlines
Deal found 11/20$182
This United Airlines deal was found by Cheapflights users on 11/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/187:38 pmBOS - ORD
1 stop4h 42mUnited Airlines
mié. 12/259:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 11/20$183
This Mytrip deal was found by Cheapflights users on 11/18. 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. 12/56:00 amBDL - ORD
2 stops18h 07mSpirit Airlines
mar. 12/105:00 amORD - BDL
1 stop16h 02mSpirit Airlines
Deal found 11/18$222
This American Airlines deal was found by Cheapflights users on 11/20. 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.
jue. 12/52:24 pmORH - ORD
1 stop21h 37mAmerican Airlines
lun. 12/94:28 pmORD - ORH
1 stop20h 26mAmerican Airlines
Deal found 11/20$222
This Delta deal was found by Cheapflights users on 11/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/297:40 pmBOS - ORD
Nonstop3h 01mDelta
vie. 1/37:35 amORD - BOS
Nonstop2h 28mDelta
Deal found 11/19$223
This Delta deal was found by Cheapflights users on 11/20. 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.
mar. 12/174:51 pmORH - ORD
1 stop6h 53mDelta
mar. 1/78:35 amORD - ORH
1 stop5h 22mDelta
Deal found 11/20$232

Find flights from Massachusetts to Chicago within your budget

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 2,629,791 searches. Data last updated noviembre 20, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 12/11

6:00 am-11:42 am

1 stop6h 42m

Chicago Midway

vie. 12/13

7:00 am-12:30 am

1 stop16h 30m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 12/11

6:00 am-8:24 am

1 stop27h 24m

Chicago O'Hare Intl

dom. 12/15

9:35 am-12:30 am

1 stop13h 55m

$124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 12/10

5:00 am-4:06 pm

1 stop12h 06m

Chicago O'Hare Intl

mar. 12/17

5:38 pm-12:35 am

1 stop5h 57m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

sáb. 12/7

5:00 am-4:06 pm

1 stop12h 06m

Chicago O'Hare Intl

mar. 12/10

9:58 am-12:38 am

1 stop13h 40m

$134

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

vie. 12/6

6:00 am-8:06 am

Nonstop3h 06m

Chicago O'Hare Intl

mié. 12/11

8:51 am-12:13 pm

Nonstop2h 22m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

mié. 12/4

7:00 am-8:45 am

Nonstop2h 45m

Chicago Midway

vie. 12/6

6:25 pm-9:35 pm

Nonstop2h 10m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mié. 1/1

6:02 am-8:05 am

Nonstop3h 03m

Chicago O'Hare Intl

lun. 2/3

9:10 am-3:41 pm

1 stop5h 31m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

mar. 12/31

6:45 am-8:49 am

Nonstop3h 04m

Chicago O'Hare Intl

dom. 1/5

8:30 pm-12:15 am

Nonstop2h 45m

$194

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

jue. 1/2

7:40 pm-9:41 pm

Nonstop3h 01m

Chicago O'Hare Intl

dom. 1/5

7:35 am-11:03 am

Nonstop2h 28m

$199

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

jue. 2/20

5:10 am-11:58 pm

1 stop19h 48m

Chicago Midway

dom. 2/23

6:38 pm-3:05 pm

1 stop19h 27m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

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.

Travel insights for flights from Massachusetts to Chicago

Get recent, data-driven insights about flights from Massachusetts to Chicago including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $232). Flying from Massachusetts to Chicago in June is currently the most expensive (average of $308). 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 noviembre 20, 2024.

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 noviembre 20, 2024.

The most flights from USMA to CHI are scheduled on a Monday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (16 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 noviembre 20, 2024.
Read through reviews of airlines operating flights from Massachusetts to Chicago, such as American Airlines, Frontier and Spirit Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very good
9,461 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Qatar Airways
7.5
Good
3,831 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,394 reviews
Southwest
8.1
Very good
5,014 reviews

Entertainment

7.7

Comfort

8.1

Food

7.2

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Frontier, which is currently one of the cheapest options available, starting at $74. Southwest flights start at $79 while deals on JetBlue start at $79 one-way.

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

    While some choose either Hartford Bradley Intl - Chicago O'Hare Intl or Boston Logan Intl - Chicago Midway, 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: Avianca (100%), Japan Airlines (96%), Republic Airways (93%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $909, our data indicates the cheapest price to be $75. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $101.

  • 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, September is the cheapest month in which you can book a flight from Massachusetts to Chicago (average of $232). Flying from Massachusetts to Chicago in June is currently the most expensive (average of $308). 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.

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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 2,629,791 searches. Data last updated noviembre 20, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$104FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$234FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$360FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$134FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$135Average$266FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$145Average$234FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$147Average$312FlexibilityNo cancel feeOn-time69%
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