Chicago

$79+ 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 2/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Jan 3 — Jan 101
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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 December 29, 2024.

Round-trip from

$150
(Frontier)

One-way from

$79
(Southwest)
From Massachusetts to Chicago (CHI)
One-way flight from Massachusetts to Chicago (CHI)

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 December 29, 2024.

This Frontier deal was found by Cheapflights users on 12/28. 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.
Tue 12/315:45 amBOS - ORD
1 stop11h 43mFrontier
Sun 1/510:14 pmORD - BOS
1 stop8h 19mFrontier
Deal found 12/28$270
This Kiwi.com deal was found by Cheapflights users on 12/28. 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.
Tue 12/315:45 amBOS - ORD
1 stop11h 43mMultiple Airlines
Fri 1/38:14 pmORD - BOS
1 stop12h 44mMultiple Airlines
Deal found 12/28$276
This American Airlines deal was found by Cheapflights users on 12/28. 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 12/318:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Sat 1/48:30 pmORD - BOS
Nonstop2h 45mAmerican Airlines
Deal found 12/28$297
This Delta deal was found by Cheapflights users on 12/27. 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.
Tue 12/317:40 amBOS - ORD
1 stop7h 58mDelta
Fri 1/312:00 pmORD - BOS
Nonstop2h 25mDelta
Deal found 12/27$307
This United Airlines deal was found by Cheapflights users on 12/28. 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 12/287:42 pmBDL - ORD
2 stops17h 07mUnited Airlines
Sun 12/292:00 pmORD - BDL
Nonstop2h 14mUnited Airlines
Deal found 12/28$318
This Southwest deal was found by Cheapflights users on 12/27. 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.
Tue 12/3112:20 pmBOS - MDW
1 stop7h 25mSouthwest
Fri 1/38:30 pmMDW - BOS
Nonstop2h 10mSouthwest
Deal found 12/27$327
This JetBlue deal was found by Cheapflights users on 12/28. 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.
Mon 12/306:00 amBOS - ORD
Nonstop3h 07mJetBlue
Sat 1/410:11 amORD - BOS
1 stop4h 48mJetBlue
Deal found 12/28$331
This Frontier deal was found by Cheapflights users on 12/28. 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.
Mon 12/3011:55 amBOS - MDW
1 stop12h 25mFrontier
Sat 1/42:20 pmMDW - BOS
1 stop9h 10mFrontier
Deal found 12/28$338
This Delta deal was found by Cheapflights users on 12/28. 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.
Tue 12/3112:20 pmBOS - MDW
1 stop4h 50mDelta
Sun 1/59:30 amMDW - BOS
1 stop5h 55mDelta
Deal found 12/28$346
This United Airlines deal was found by Cheapflights users on 12/28. 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.
Tue 12/316:02 amBOS - ORD
Nonstop3h 03mUnited Airlines
Wed 1/19:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 12/28$347
This Southwest deal was found by Cheapflights users on 12/27. 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.
Mon 12/3010:35 pmBOS - ORD
2 stops15h 25mSouthwest
Fri 1/33:10 pmORD - BOS
1 stop8h 10mSouthwest
Deal found 12/27$356
This CheapOair deal was found by Cheapflights users on 12/29. 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.
Mon 12/306:05 pmBDL - MDW
1 stop6h 09mFrontier
Fri 1/36:49 pmMDW - BDL
1 stop13h 47mFrontier
Deal found 12/29$424

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 2,558,603 searches. Data last updated December 29, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 3/13

6:00 am-7:35 pm

1 stop14h 35m

Chicago Midway

Sat 3/15

12:49 pm-12:34 am

1 stop10h 45m

$150

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 1/14

6:00 am-1:34 pm

1 stop8h 34m

Chicago O'Hare Intl

Fri 1/17

10:02 pm-12:27 am

1 stop25h 25m

$150

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/16

6:00 am-2:32 pm

1 stop9h 32m

Chicago O'Hare Intl

Thu 1/23

4:41 pm-12:39 am

1 stop6h 58m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 1/31

6:10 am-8:14 am

Nonstop3h 04m

Chicago O'Hare Intl

Wed 2/5

7:00 am-10:15 am

Nonstop2h 15m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/23

8:10 am-10:05 am

Nonstop2h 55m

Chicago Midway

Sun 1/26

8:40 am-11:55 am

Nonstop2h 15m

$158

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/23

2:52 pm-4:52 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 1/26

12:30 pm-3:49 pm

Nonstop2h 19m

$159

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 2/22

10:03 am-11:58 pm

1 stop14h 55m

Chicago O'Hare Intl

Wed 2/26

3:14 pm-11:47 pm

1 stop7h 33m

$160

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 1/12

6:00 am-8:03 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 1/12

4:15 pm-7:38 pm

Nonstop2h 23m

$198

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/9

8:20 pm-10:23 pm

Nonstop3h 03m

Chicago O'Hare Intl

Sat 1/18

7:10 am-10:47 am

Nonstop2h 37m

$202

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 1/23

2:32 pm-10:47 am

1 stop21h 15m

Chicago O'Hare Intl

Sun 1/26

4:22 pm-2:02 pm

1 stop20h 40m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

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, 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 $317). 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 December 29, 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 December 29, 2024.

The most flights from USMA to CHI are scheduled on a Friday (56 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (14 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 December 29, 2024.
Read through reviews of airlines operating flights from Massachusetts to Chicago, such as Spirit Airlines, JetBlue and United Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,722 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.1
Very good
4,722 reviews
8.1
Very good
4,722 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
9,582 reviews
8.1
Very good
4,722 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

8.0
Very good
8,546 reviews
8.1
Very good
4,722 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
3,235 reviews
8.1
Very good
4,722 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

7.4
Good
8,986 reviews
8.1
Very good
4,722 reviews

Boarding

8.2

Crew

8.7

Comfort

8.1

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Southwest, which is currently one of the cheapest options available, starting at $79. United Airlines flights start at $79 while deals on Frontier start at $80 one-way.

  • What are the most popular routes 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 (98%), Japan Airlines (95%), Spirit Airlines (94%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $918, our data indicates the cheapest price to be $78. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $106.

  • 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 $317). 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 Chicago

See prices for flight routes from nearby airports that may be better suited for you.

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 December 29, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$81Average$232FlexibilityNo cancel feeOn-time62%
DeltaCheapest$93Average$357FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$144FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$266FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$318FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$148Average$294FlexibilityNo cancel feeOn-time63%
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