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$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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
Mar 9 — Mar 161
Sun 3/9
Sun 3/16
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 March 4, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$155
(Booking.com)

One-way from

$79
(Southwest)

Popular in

April

Cheapest in

September

Average price

$276

Good round-trip deal

$240 or less

Good one-way deal

$115 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. 13% potential increase in price ($38 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 4, 2025.

This Booking.com deal was found by Cheapflights users on 3/3. 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.
Thu 3/275:10 amBOS - ORD
1 stop6h 40mMultiple Airlines
Tue 4/17:21 pmORD - BOS
1 stop13h 38mMultiple Airlines
Deal found 3/3$155
This Mytrip deal was found by Cheapflights users on 3/4. 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.
Fri 3/216:13 pmBOS - ORD
2 stops32h 25mSpirit Airlines
Mon 3/248:33 pmORD - BOS
1 stop19h 41mSpirit Airlines
Deal found 3/4$156
This Southwest deal was found by Cheapflights users on 3/3. 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.
Fri 5/25:45 amBOS - MDW
Nonstop2h 35mSouthwest
Mon 5/55:30 amMDW - BOS
Nonstop2h 15mSouthwest
Deal found 3/3$157
This Delta deal was found by Cheapflights users on 3/3. 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 4/27:25 amBOS - ORD
Nonstop3h 09mDelta
Sat 4/127:00 amORD - BOS
Nonstop2h 28mDelta
Deal found 3/3$157
This Frontier deal was found by Cheapflights users on 3/4. 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.
Thu 4/312:54 pmBOS - MDW
1 stop9h 46mFrontier
Wed 4/912:46 pmMDW - BOS
1 stop11h 01mFrontier
Deal found 3/4$160
This CheapOair deal was found by Cheapflights users on 3/3. 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.
Wed 3/266:00 amBOS - ORD
1 stop12h 26mFrontier
Thu 3/2711:55 amORD - BOS
1 stop11h 49mFrontier
Deal found 3/3$160
This American Airlines deal was found by Cheapflights users on 3/4. 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.
Mon 3/242:12 pmORH - ORD
1 stop21h 39mAmerican Airlines
Mon 3/314:27 pmORD - ORH
1 stop20h 13mAmerican Airlines
Deal found 3/4$162
This JetBlue deal was found by Cheapflights users on 3/4. 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.
Tue 4/85:10 amBOS - ORD
1 stop8h 16mJetBlue
Fri 4/118:29 pmORD - BOS
Nonstop2h 29mJetBlue
Deal found 3/4$162
This United Airlines deal was found by Cheapflights users on 3/3. 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 3/245:30 amBOS - ORD
1 stop5h 08mUnited Airlines
Tue 3/252:15 pmORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 3/3$163
This American Airlines deal was found by Cheapflights users on 3/3. 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.
Fri 4/48:59 pmBOS - ORD
Nonstop2h 58mAmerican Airlines
Tue 4/88:05 amORD - BOS
Nonstop2h 25mAmerican Airlines
Deal found 3/3$174
This Mytrip deal was found by Cheapflights users on 3/3. 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.
Wed 4/210:45 amBDL - ORD
2 stops22h 59mMultiple Airlines
Wed 4/93:32 pmORD - BDL
3 stops29h 48mMultiple Airlines
Deal found 3/3$208
This Mytrip deal was found by Cheapflights users on 3/3. 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 3/1711:36 amBDL - ORD
1 stop22h 31mSpirit Airlines
Tue 3/187:42 pmORD - BDL
1 stop13h 08mSpirit Airlines
Deal found 3/3$209

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 March 4, 2025.

Fly from

Massachusetts

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/27

5:10 am-10:50 am

1 stop6h 40m

Chicago O'Hare Intl

Tue 4/1

7:21 pm-9:59 am

1 stop13h 38m

$155

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 3/21

6:13 pm-1:38 am

2 stops32h 25m

Chicago O'Hare Intl

Mon 3/24

8:33 pm-5:14 pm

1 stop19h 41m

$156

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 5/2

5:45 am-7:20 am

Nonstop2h 35m

Chicago Midway

Mon 5/5

5:30 am-8:45 am

Nonstop2h 15m

$157

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/2

7:43 am-9:40 am

Nonstop2h 57m

Chicago O'Hare Intl

Fri 4/4

7:10 am-10:38 am

Nonstop2h 28m

$157

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 4/3

12:54 pm-9:40 pm

1 stop9h 46m

Chicago Midway

Wed 4/9

12:46 pm-12:47 am

1 stop11h 01m

$160

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 3/26

6:00 am-5:26 pm

1 stop12h 26m

Chicago O'Hare Intl

Thu 3/27

11:55 am-12:44 am

1 stop11h 49m

$160

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 3/24

2:12 pm-10:51 am

1 stop21h 39m

Chicago O'Hare Intl

Mon 3/31

4:27 pm-1:40 pm

1 stop20h 13m

$162

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/8

5:10 am-12:26 pm

1 stop8h 16m

Chicago O'Hare Intl

Sat 4/12

8:29 pm-11:58 pm

Nonstop2h 29m

$162

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/27

7:25 am-9:34 am

Nonstop3h 09m

Chicago O'Hare Intl

Thu 4/3

7:00 am-10:28 am

Nonstop2h 28m

$167

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 4/4

5:00 am-6:55 am

Nonstop2h 55m

Chicago O'Hare Intl

Wed 4/9

4:49 pm-8:09 pm

Nonstop2h 20m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/3

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 $326). 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 March 4, 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.

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 March 4, 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
4,331 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Southwest
8.1
Very good
4,331 reviews
Southwest
8.1
Very good
4,331 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Alaska Airlines
8.0
Very good
9,713 reviews
Southwest
8.1
Very good
4,331 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Delta
8.0
Very good
8,061 reviews
Southwest
8.1
Very good
4,331 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Qatar Airways
7.4
Good
3,562 reviews
Southwest
8.1
Very good
4,331 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

United Airlines
7.4
Good
8,678 reviews
Southwest
8.1
Very good
4,331 reviews

Crew

8.7

Overall

8.1

Entertainment

7.6

Comfort

8.1

Food

7.1

Boarding

8.2

Reviews

1 / 20

8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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. JetBlue flights start at $79 while deals on Spirit Airlines start at $80 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: Air France (100%), LATAM Airlines (100%), Virgin Atlantic (91%).

  • What are the cheapest flights from Massachusetts to Chicago?

    Looking for the cheapest flight from Massachusetts to Chicago? While on average our users pay $774, our data indicates the cheapest price to be $78. The most popular route (Boston Logan Intl - Chicago O'Hare Intl), is priced around $95.

  • 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 $326). 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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Philadelphia to Midway flights
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Boston to Midway flights

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 March 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$39Average$105FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$87Average$235FlexibilityNo cancel feeOn-time62%
DeltaCheapest$96Average$356FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$98Average$145FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$264FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$312FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$152Average$243FlexibilityNo cancel feeOn-time63%
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