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$59+ 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheap flight deals from Chicago to Massachusetts

Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$116
(American Airlines)

One-way from

$59
(JetBlue)

Popular in

April

Cheapest in

September

Average price

$293

Good round-trip deal

$164 or less

Good one-way deal

$58 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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From Chicago (CHI) to Massachusetts
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One-way flight from Chicago (CHI) to Massachusetts
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Highest demand for flights based on searches. 11% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Massachusetts.
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Price to beat on a one-way flight from Chicago (CHI) to Massachusetts.
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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 April 24, 2025.

This American Airlines deal was found by Cheapflights users on 4/23. 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 5/37:05 amORD - BOS
Nonstop2h 28mAmerican Airlines
Tue 5/61:02 pmBOS - ORD
Nonstop2h 59mAmerican Airlines
Deal found 4/23$116
This United Airlines deal was found by Cheapflights users on 4/23. 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 5/104:20 pmORD - BOS
Nonstop2h 28mUnited Airlines
Sun 8/246:00 amBOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 4/23$117
This Southwest deal was found by Cheapflights users on 4/23. 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.
Sat 5/106:30 pmMDW - BOS
Nonstop2h 15mSouthwest
Tue 5/135:50 amBOS - MDW
Nonstop2h 40mSouthwest
Deal found 4/23$117
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/135:05 amORD - BOS
1 stop8h 39mSpirit Airlines
Tue 5/203:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Deal found 4/22$128
This Southwest deal was found by Cheapflights users on 4/23. 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 6/64:00 pmORD - BOS
1 stop7h 05mSouthwest
Tue 6/105:45 amBOS - ORD
1 stop7h 05mSouthwest
Deal found 4/23$136
This Priceline deal was found by Cheapflights users on 4/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/104:15 pmORD - BOS
1 stop7h 29mMultiple Airlines
Wed 5/143:49 pmBOS - ORD
1 stop8h 15mMultiple Airlines
Deal found 4/23$143
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Fri 5/307:31 pmORD - BOS
Nonstop2h 29mJetBlue
Wed 6/46:00 amBOS - ORD
Nonstop3h 00mJetBlue
Deal found 4/23$148
This American Airlines deal was found by Cheapflights users on 4/23. 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.
Wed 4/305:10 pmORD - ORH
1 stop19h 15mAmerican Airlines
Sat 5/31:38 pmORH - ORD
1 stop22h 27mAmerican Airlines
Deal found 4/23$154
This Delta deal was found by Cheapflights users on 4/24. 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 6/196:59 pmORD - BOS
Nonstop2h 46mDelta
Mon 6/237:20 amBOS - ORD
Nonstop2h 58mDelta
Deal found 4/24$177
This Frontier deal was found by Cheapflights users on 4/23. 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.
Sat 5/104:15 pmORD - BOS
1 stop7h 29mFrontier
Mon 5/1212:58 pmBOS - ORD
1 stop11h 13mFrontier
Deal found 4/23$188
This CheapOair deal was found by Cheapflights users on 4/23. 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 5/121:19 pmMDW - BOS
1 stop10h 25mFrontier
Wed 5/148:00 amBOS - MDW
1 stop29h 24mFrontier
Deal found 4/23$191
This Delta deal was found by Cheapflights users on 4/23. 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 5/207:00 amORD - ORH
1 stop7h 05mDelta
Tue 5/274:10 pmORH - ORD
1 stop7h 31mDelta
Deal found 4/23$212

Cheapflights Fare Finder

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 2,558,603 searches. Data last updated April 24, 2025.
Use the filters below to find and compare flights from Chicago to Massachusetts that are best for you.

Fly from

Chicago

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 5/5

6:35 pm-10:07 pm

Nonstop2h 32m

Boston Logan Intl

Fri 5/9

8:51 pm-10:52 pm

Nonstop3h 01m

$116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/10

4:20 pm-7:48 pm

Nonstop2h 28m

Boston Logan Intl

Sun 8/24

6:00 am-7:56 am

Nonstop2h 56m

$117

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 5/10

6:30 pm-9:45 pm

Nonstop2h 15m

Boston Logan Intl

Tue 5/13

5:50 am-7:30 am

Nonstop2h 40m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/13

12:41 pm-11:29 pm

1 stop9h 48m

Boston Logan Intl

Wed 5/21

3:49 pm-11:04 pm

1 stop8h 15m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 6/6

4:00 pm-12:05 am

1 stop7h 05m

Boston Logan Intl

Tue 6/10

5:45 am-11:50 am

1 stop7h 05m

$136

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/10

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Wed 5/14

3:49 pm-11:04 pm

1 stop8h 15m

$143

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/30

7:31 pm-11:00 pm

Nonstop2h 29m

Boston Logan Intl

Tue 6/3

6:00 am-8:00 am

Nonstop3h 00m

$148

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Fri 5/9

4:44 pm-1:45 pm

1 stop20h 01m

Worcester

Tue 5/13

1:46 pm-5:34 pm

1 stop4h 48m

$154

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/19

6:59 pm-10:45 pm

Nonstop2h 46m

Boston Logan Intl

Mon 6/23

7:20 am-9:18 am

Nonstop2h 58m

$177

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/10

4:15 pm-12:44 am

1 stop7h 29m

Boston Logan Intl

Mon 5/12

12:58 pm-11:11 pm

1 stop11h 13m

$188

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Massachusetts

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 April 24, 2025.

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.

Weekly flight availability from Chicago to Massachusetts

Explore weekly flight availability from Chicago to Massachusetts. 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 April 24, 2025.

The most flights from CHI to USMA are scheduled on a Monday (67 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

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 April 24, 2025.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,918 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,920 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Qatar Airways
7.4
Good
3,561 reviews
Alaska Airlines
8.0
Very good
9,918 reviews

Food

7.1

Crew

8.5

Comfort

7.9

Boarding

8.2

Entertainment

7.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

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

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from Southwest and Spirit Airlines, 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?

    When deciding which route to take from Chicago to Massachusetts consider Chicago O'Hare Intl - Boston Logan Intl, Chicago Midway - Boston Logan Intl or Chicago O'Hare Intl - Hartford Bradley Intl as they are the most popular.

  • 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: Air France (100%), Iberia (91%), Virgin Atlantic( 88%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $48. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $111 on average our data indicates $613 when flying from Chicago to Massachusetts.

  • 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.

  • 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.
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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 2,558,603 searches. Data last updated April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$95FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$298FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$115FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$79Average$487FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$415FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$140Average$387FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$293FlexibilityNo cancel feeOn-time63%

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