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$55+ 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 2/27. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
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 January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$145
(Booking.com)

One-way from

$55
(Frontier)

Popular in

April

Cheapest in

September

Average price

$202

Good round-trip deal

$222 or less

Good one-way deal

$124 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 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. 14% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Booking.com deal was found by Cheapflights users on 1/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/16:00 amBOS - MDW
1 stop17h 51mFrontier
Sun 3/212:43 pmMDW - BOS
1 stop22h 02mFrontier
Deal found 1/29$145
This CheapOair deal was found by Cheapflights users on 1/29. 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.
Sun 2/236:00 amBOS - ORD
1 stop28h 27mFrontier
Tue 2/256:20 amORD - BOS
1 stop17h 11mFrontier
Deal found 1/29$145
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/245:07 pmBOS - ORD
2 stops20h 30mSpirit Airlines
Tue 2/257:13 pmORD - BOS
1 stop17h 16mSpirit Airlines
Deal found 1/29$146
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/116:00 amBOS - ORD
1 stop8h 36mMultiple Airlines
Mon 2/177:13 pmORD - BOS
1 stop26h 28mMultiple Airlines
Deal found 1/28$147
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/195:40 pmBOS - MDW
Nonstop2h 50mSouthwest
Tue 2/256:25 pmMDW - BOS
Nonstop2h 15mSouthwest
Deal found 1/28$157
This Delta deal was found by Cheapflights users on 1/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/248:20 pmBOS - ORD
Nonstop2h 59mDelta
Fri 2/282:35 pmORD - BOS
Nonstop2h 31mDelta
Deal found 1/29$157
This JetBlue deal was found by Cheapflights users on 1/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/83:52 pmBOS - ORD
Nonstop3h 03mJetBlue
Thu 2/137:00 amORD - BOS
Nonstop2h 22mJetBlue
Deal found 1/29$177
This American Airlines deal was found by Cheapflights users on 1/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/81:38 pmBOS - ORD
Nonstop3h 03mAmerican Airlines
Tue 3/118:36 pmORD - BOS
Nonstop2h 30mAmerican Airlines
Deal found 1/29$178
This United Airlines deal was found by Cheapflights users on 1/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/104:17 pmBOS - ORD
1 stop6h 43mUnited Airlines
Wed 3/126:13 pmORD - BOS
Nonstop2h 24mUnited Airlines
Deal found 1/29$183
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/135:45 amBOS - ORD
1 stop9h 15mSouthwest
Sun 2/1611:25 amORD - BOS
1 stop4h 10mSouthwest
Deal found 1/29$228
This Delta deal was found by Cheapflights users on 1/30. 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 5/64:00 pmORH - ORD
1 stop5h 16mDelta
Thu 5/88:30 amORD - ORH
1 stop5h 35mDelta
Deal found 1/30$252
This Delta deal was found by Cheapflights users on 1/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/175:48 amBDL - MDW
1 stop3h 54mDelta
Wed 4/235:59 pmMDW - BDL
1 stop4h 35mDelta
Deal found 1/29$277

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 2/23

6:00 am-9:27 am

1 stop28h 27m

Chicago O'Hare Intl

Tue 2/25

6:20 am-12:31 am

1 stop17h 11m

$145

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 2/24

5:07 pm-12:37 pm

2 stops20h 30m

Chicago O'Hare Intl

Tue 2/25

7:13 pm-1:29 pm

1 stop17h 16m

$146

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 2/11

6:00 am-1:36 pm

1 stop8h 36m

Chicago O'Hare Intl

Mon 2/17

7:13 pm-10:41 pm

1 stop26h 28m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 2/28

6:00 am-7:19 pm

1 stop14h 19m

Chicago Midway

Sun 3/2

12:43 pm-11:45 am

1 stop22h 02m

$149

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 2/21

7:45 pm-9:35 pm

Nonstop2h 50m

Chicago Midway

Fri 2/28

8:20 pm-11:35 pm

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 2/24

8:20 pm-10:19 pm

Nonstop2h 59m

Chicago O'Hare Intl

Fri 2/28

6:25 pm-10:04 pm

Nonstop2h 39m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 3/8

1:38 pm-3:41 pm

Nonstop3h 03m

Chicago O'Hare Intl

Tue 3/11

8:36 pm-12:06 am

Nonstop2h 30m

$178

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 3/10

4:17 pm-10:00 pm

1 stop6h 43m

Chicago O'Hare Intl

Wed 3/12

6:13 pm-9:37 pm

Nonstop2h 24m

$183

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 2/10

3:52 pm-5:55 pm

Nonstop3h 03m

Chicago O'Hare Intl

Sat 2/15

5:40 pm-12:18 am

1 stop5h 38m

$187

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 2/24

2:15 pm-10:45 am

1 stop21h 30m

Chicago O'Hare Intl

Fri 2/28

4:14 pm-1:43 pm

1 stop20h 29m

$214

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/30

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 $325). 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 January 30, 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 January 30, 2025.

The most flights from USMA to CHI 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 (12 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 January 30, 2025.
Read through reviews of airlines operating flights from Massachusetts to Chicago, such as Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Alaska Airlines
8.0
Very good
9,688 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Delta
8.0
Very good
8,454 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

Qatar Airways
7.5
Good
3,718 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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.

JetBlue
7.4
Good
3,156 reviews
Southwest
8.1
Very good
4,585 reviews

Boarding

8.2

Entertainment

7.7

Food

7.1

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 20

6.0
Good

Lauren,Dec 2024

MCI - DCA

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 Frontier, which is currently one of the cheapest options available, starting at $55. Spirit Airlines flights start at $70 while deals on Southwest start at $79 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: Air France (100%), Spirit Airlines (100%), Cathay Pacific (96%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $884, our data indicates the cheapest price to be $78. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $84.

  • 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 $325). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$106FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$82Average$238FlexibilityNo cancel feeOn-time62%
DeltaCheapest$94Average$356FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$144FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$138Average$265FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$312FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$149Average$239FlexibilityNo cancel feeOn-time63%
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