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$69+ 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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
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 August 13, 2025.

Round-trip from

$136
(FlightHub)

One-way from

$69
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$220

Good round-trip deal

$137 or less

Good one-way deal

$68 or less
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. 8% potential increase in price ($20 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 August 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 August 13, 2025.

This FlightHub deal was found by Cheapflights users on 8/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/311:36 amORD - BOS
1 stop11h 13mSpirit Airlines
Sat 9/63:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Deal found 8/12$136
This American Airlines deal was found by Cheapflights users on 8/11. 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 8/198:25 pmORD - BOS
Nonstop2h 34mAmerican Airlines
Thu 8/215:28 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 8/11$137
This JetBlue deal was found by Cheapflights users on 8/12. 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 9/197:50 pmORD - BOS
Nonstop2h 35mJetBlue
Sun 9/217:00 amBOS - ORD
Nonstop2h 56mJetBlue
Deal found 8/12$138
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Fri 9/269:37 pmORD - BOS
Nonstop2h 32mUnited Airlines
Mon 9/298:02 pmBOS - ORD
1 stop4h 55mUnited Airlines
Deal found 8/12$139
This CheapOair deal was found by Cheapflights users on 8/12. 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 10/156:00 amORD - BOS
1 stop6h 44mSpirit Airlines
Wed 10/226:11 amBOS - ORD
1 stop13h 13mSpirit Airlines
Deal found 8/12$140
This United Airlines deal was found by Cheapflights users on 8/12. 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.
Sun 8/249:15 pmORD - BOS
Nonstop2h 30mUnited Airlines
Tue 9/211:00 amBOS - ORD
Nonstop2h 50mUnited Airlines
Deal found 8/12$142
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/89:42 amORD - BOS
Nonstop2h 28mJetBlue
Wed 10/157:00 amBOS - ORD
Nonstop2h 57mJetBlue
Deal found 8/13$143
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Sat 9/1311:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Wed 9/1712:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/11$145
This Kiwi.com deal was found by Cheapflights users on 8/11. 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.
Wed 9/1011:57 amORD - BOS
1 stop11h 00mSpirit Airlines
Sat 9/1312:20 pmBOS - ORD
1 stop10h 38mSpirit Airlines
Deal found 8/11$146
This Delta deal was found by Cheapflights users on 8/12. 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 10/67:10 pmORD - BOS
Nonstop2h 35mDelta
Tue 10/147:30 pmBOS - ORD
Nonstop2h 49mDelta
Deal found 8/12$147
This JetBlue deal was found by Cheapflights users on 8/12. 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 10/76:50 pmORD - BOS
Nonstop2h 33mJetBlue
Wed 10/87:00 amBOS - ORD
Nonstop2h 57mJetBlue
Deal found 8/12$148
This Kiwi.com deal was found by Cheapflights users on 8/11. 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 9/911:13 amORD - BOS
2 stops10h 57mSpirit Airlines
Wed 9/173:00 pmBOS - ORD
1 stop8h 48mSpirit Airlines
Deal found 8/11$150

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 August 13, 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

Tue 8/19

6:15 am-9:43 am

Nonstop2h 28m

Boston Logan Intl

Tue 8/26

5:28 am-7:24 am

Nonstop2h 56m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 10/8

7:05 am-10:29 am

Nonstop2h 24m

Boston Logan Intl

Sat 10/18

4:10 pm-6:07 pm

Nonstop2h 57m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 9/28

6:05 am-9:32 am

Nonstop2h 27m

Boston Logan Intl

Fri 10/3

5:00 am-6:51 am

Nonstop2h 51m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 10/11

8:25 pm-11:54 pm

Nonstop2h 29m

Boston Logan Intl

Wed 10/15

5:24 am-7:25 am

Nonstop3h 01m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/17

6:05 am-9:32 am

Nonstop2h 27m

Boston Logan Intl

Sun 9/21

5:00 am-6:51 am

Nonstop2h 51m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 10/7

9:42 am-1:10 pm

Nonstop2h 28m

Boston Logan Intl

Mon 10/13

7:00 am-8:57 am

Nonstop2h 57m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/19

7:50 pm-11:25 pm

Nonstop2h 35m

Boston Logan Intl

Sun 9/21

7:00 am-8:56 am

Nonstop2h 56m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/25

9:51 am-1:20 pm

Nonstop2h 29m

Boston Logan Intl

Tue 9/30

7:00 am-8:56 am

Nonstop2h 56m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 10/8

6:50 pm-10:23 pm

Nonstop2h 33m

Boston Logan Intl

Tue 10/14

4:05 pm-5:55 pm

Nonstop2h 50m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/10

9:51 am-1:20 pm

Nonstop2h 29m

Boston Logan Intl

Mon 9/15

4:40 pm-6:55 pm

Nonstop3h 15m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

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 August 13, 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 August 13, 2025.

The most flights from CHI to USMA are scheduled on a Monday (85 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

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 August 13, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from Chicago to Massachusetts to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,979 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,920 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
JetBlue
7.2
Good
2,915 reviews
Southwest
8.0
Very good
4,246 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

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 American Airlines, with whom users have recently found tickets for as low as $69. 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: Etihad Airways (94%), Alaska Airlines (78%), Envoy Air( 78%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $68. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $99 on average our data indicates $405 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.

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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 August 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$33Average$101FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$77Average$380FlexibilityNo cancel feeOn-time62%
DeltaCheapest$91Average$256FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$121Average$443FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$130Average$400FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$263FlexibilityNo cancel feeOn-time63%

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