Massachusetts

$46+ Cheap flights from Chicago (CHI) to Massachusetts

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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
nov. 5 — nov. 121
1 adult
mar. 11/5
mar. 11/12
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Find flight deals from Chicago to Massachusetts

Cheapest flights from Chicago to Massachusetts
Explore the most affordable flight options available from Chicago to Massachusetts. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 31, 2024.

This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/154:38 pmORD - BOS
Nonstop2h 19mSpirit Airlines
sáb. 11/235:30 amBOS - ORD
Nonstop3h 07mSpirit Airlines
Deal found 10/30$91
This CheapOair deal was found by Cheapflights users on 10/31. 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.
jue. 11/77:05 pmORD - BOS
1 stop4h 26mMultiple Airlines
mar. 11/127:40 amBOS - ORD
Nonstop3h 10mMultiple Airlines
Deal found 10/31$97
This Frontier deal was found by Cheapflights users on 10/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/21:39 pmORD - BOS
1 stop9h 49mFrontier
mié. 11/66:00 amBOS - ORD
1 stop8h 32mFrontier
Deal found 10/29$100
This Frontier deal was found by Cheapflights users on 10/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/412:57 pmMDW - BOS
1 stop10h 33mFrontier
mar. 12/106:00 amBOS - MDW
1 stop6h 42mFrontier
Deal found 10/30$105
This JetBlue deal was found by Cheapflights users on 10/31. 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.
mié. 12/48:50 amORD - BOS
Nonstop2h 22mJetBlue
lun. 12/96:00 amBOS - ORD
Nonstop3h 06mJetBlue
Deal found 10/31$117
This Delta deal was found by Cheapflights users on 10/31. 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.
jue. 11/146:40 amORD - BOS
Nonstop2h 20mDelta
lun. 11/183:45 pmBOS - ORD
Nonstop3h 01mDelta
Deal found 10/31$118
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/67:30 amORD - BOS
Nonstop2h 19mUnited Airlines
dom. 12/86:00 amBOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 10/30$123
This Southwest deal was found by Cheapflights users on 10/29. 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.
vie. 12/138:30 pmMDW - BOS
Nonstop2h 10mSouthwest
dom. 12/156:40 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 10/29$124
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/258:05 amORD - BOS
Nonstop2h 21mAmerican Airlines
vie. 1/38:45 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 10/30$158
This FareScan deal was found by Cheapflights users on 10/30. 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 FareScan is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/197:49 amORD - BDL
2 stops32h 12mSpirit Airlines
vie. 11/225:55 pmBDL - ORD
2 stops29h 11mSpirit Airlines
Deal found 10/30$184
This CheapOair deal was found by Cheapflights users on 10/31. 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.
lun. 11/258:21 pmORD - BDL
1 stop13h 08mMultiple Airlines
mar. 12/106:00 amBDL - ORD
1 stop16h 07mMultiple Airlines
Deal found 10/31$198
This Southwest deal was found by Cheapflights users on 10/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/1811:25 amORD - BOS
2 stops6h 40mSouthwest
mar. 11/196:00 amBOS - ORD
2 stops8h 00mSouthwest
Deal found 10/30$199

Find flights from Chicago to Massachusetts within your budget

Customize your flight search to find flights from Chicago to Massachusetts 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 2,570,725 searches. Data last updated octubre 31, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

dom. 1/19

4:21 pm-12:29 am

1 stop7h 08m

$69

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 12/4

11:45 am-12:38 am

1 stop11h 53m

$70

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

dom. 1/12

6:30 am-9:58 am

Nonstop2h 28m

$79

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 11/9

3:45 pm-7:06 pm

Nonstop2h 21m

$81

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 12/6

7:15 am-1:00 pm

1 stop4h 45m

$81

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 11/26

6:00 am-9:17 am

Nonstop2h 17m

$89

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

mar. 12/3

5:00 am-11:17 pm

2 stops17h 17m

$99

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 11/12

7:00 am-10:20 am

Nonstop2h 20m

$101

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

dom. 1/19

7:00 am-10:46 am

1 stop26h 46m

$72

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 12/21

8:05 pm-11:09 pm

1 stop26h 04m

$188

Flights are sorted by cheapest first

Deals found on 10/29

Showing 1-10 of 60 results
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Best time to book a flight from Chicago to Massachusetts

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

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

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

Currently, January is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $218). Flying from Chicago to Massachusetts in July is currently the most expensive (average of $311). 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 CHI to MA?

Find hourly flight availability from Chicago to Massachusetts. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated octubre 31, 2024.

When flying from Chicago to Massachusetts, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Massachusetts by month

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

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

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

If weather is an important factor for your trip to Massachusetts, 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 30.2 F).

Reviews of airlines servicing Massachusetts

Get insights into the airlines that provide service to Massachusetts. 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 Massachusetts. Reviews last updated octubre 31, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Spirit Airlines, Southwest and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

8.1
Very good
5,116 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

8.0
Very good
9,420 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

8.0
Very good
8,835 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

7.5
Good
3,900 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

Reviews

1 / 10

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

7.5
Good
3,514 reviews
8.1
Very good
5,116 reviews

Crew

8.7

Boarding

8.3

Overall

8.1

Entertainment

7.7

Comfort

8.1

Food

7.2

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 Chicago to Massachusetts. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • Can I find flights from Chicago to Massachusetts for under $100 on Cheapflights?

    Yes, there are multiple flights from Chicago to Massachusetts for under $100. The cheapest flight booked recently is on Spirit Airlines for just $74, but on average you can expect to pay $180.

  • Are there nonstop flights from Chicago to Massachusetts for under $100 on Cheapflights?

    Cheapflights has at least 13 direct flights from Chicago to Massachusetts under $100. A good price for a nonstop flight from Chicago to Massachusetts is less than $211.

  • Are there last-minute flights available from Chicago to Massachusetts for under $100?

    There are currently 20+ open flights from Chicago to Massachusetts within the next 7 days for less than $100.

  • What days are nonstop flights available from Chicago to Massachusetts?

    Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

  • How many flights depart from Chicago to Massachusetts on average per day?

    124 flight departures from Chicago to Massachusetts per day on average.
    Early Morning (Midnight to 6am) - 2% of flight departures
    Morning (6am - Noon) - 42% of flight departures
    Afternoon (Noon - 6pm) - 29% of flight departures
    Evening (6pm - Midnight) - 27% of flight departures

  • How long is the flight from Chicago to Massachusetts?

    There are many flights that can get you from Chicago to Massachusetts in 2h 18m. Fly via Spirit Airlines, Frontier, or JetBlue to get the fastest option. The distance between Chicago and Massachusetts is about 869 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Massachusetts one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $46. However, be on the lookout for offers from Frontier and Delta, as they are both options that can get you from Chicago to Massachusetts for a low price.

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

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

    Before booking your flight to Massachusetts from Chicago, check out the most reliable airlines to get you to your destination on time: Republic Airways (100%), Delta (89%), Envoy Air( 86%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $77 on average our data indicates $428 when flying from Chicago to Massachusetts.

  • What does ORD to BOS mean?

    ORD stands for Chicago O'Hare Intl Airport, while BOS stands for Boston Logan Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Worcester Airport (ORH), Nantucket Memorial Airport (ACK), West Tisbury Martha's Vineyard Airport (MVY), Hyannis Barnstable Airport (HYA), New Bedford Regional Airport (EWB) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Massachusetts that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Massachusetts flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Massachusetts with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Massachusetts flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Massachusetts by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Massachusetts that allow pets onboard?

    Many airlines flying from Chicago to Massachusetts offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Massachusetts?

    Yes, you can often find last-minute deals on Chicago to Massachusetts flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Massachusetts flight deals updated?

    The Chicago to Massachusetts flight deals you see on this page were last updated on 10/31.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $218). Flying from Chicago to Massachusetts in July is currently the most expensive (average of $311). 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 Chicago to Massachusetts

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

Top 7 airlines flying from Chicago to Massachusetts

Discover the top 7 airlines that operate flights from Chicago to Massachusetts. 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 2,570,725 searches. Data last updated octubre 31, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$36Average$91FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$318FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$83Average$122FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$83Average$554FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$136Average$457FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$143Average$438FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$162Average$257FlexibilityNo cancel feeOn-time63%
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