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$64+ 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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
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 January 15, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$132
(Priceline)

One-way from

$64
(Frontier)

Popular in

April

Cheapest in

January

Average price

$207

Good round-trip deal

$171 or less

Good one-way deal

$78 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. 6% potential increase in price ($16 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 15, 2026.

This Priceline deal was found by Cheapflights users on 1/14. 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 2/77:20 am
ORD
-
BOS
1 stop8h 28m
Multiple Airlines
Sun 2/83:35 pm
BOS
-
ORD
Nonstop3h 08m
Multiple Airlines
Deal found 1/14$132
This Kiwi.com deal was found by Cheapflights users on 1/15. 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 2/187:00 am
MDW
-
BOS
1 stop17h 13m
Frontier
Fri 2/276:00 am
BOS
-
MDW
1 stop13h 38m
Frontier
Deal found 1/15$132
This Priceline deal was found by Cheapflights users on 1/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/17:45 am
ORD
-
BOS
Nonstop2h 25m
Multiple Airlines
Tue 2/36:00 am
BOS
-
ORD
1 stop8h 58m
Multiple Airlines
Deal found 1/13$133
This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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.
Sat 1/317:20 am
ORD
-
BOS
1 stop8h 08m
Spirit Airlines
Tue 2/37:00 am
BOS
-
ORD
1 stop13h 41m
Spirit Airlines
Deal found 1/14$134
This United Airlines deal was found by Cheapflights users on 1/14. 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 1/3110:35 am
ORD
-
BOS
Nonstop2h 25m
United Airlines
Fri 2/66:00 am
BOS
-
ORD
Nonstop3h 04m
United Airlines
Deal found 1/14$135
This American Airlines deal was found by Cheapflights users on 1/15. 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.
Thu 1/227:00 am
ORD
-
BOS
Nonstop2h 23m
American Airlines
Sun 1/257:00 am
BOS
-
ORD
Nonstop3h 05m
American Airlines
Deal found 1/15$136
This JetBlue deal was found by Cheapflights users on 1/15. 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.
Thu 6/48:21 pm
ORD
-
BOS
Nonstop2h 35m
JetBlue
Mon 6/86:50 am
BOS
-
ORD
Nonstop2h 55m
JetBlue
Deal found 1/15$137
This Southwest deal was found by Cheapflights users on 1/14. 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 1/305:35 pm
MDW
-
BOS
Nonstop2h 15m
Southwest
Sun 2/15:20 am
BOS
-
MDW
Nonstop2h 50m
Southwest
Deal found 1/14$137
This JetBlue deal was found by Cheapflights users on 1/14. 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.
Thu 1/227:40 am
ORD
-
BOS
Nonstop2h 25m
JetBlue
Sun 1/253:35 pm
BOS
-
ORD
Nonstop3h 08m
JetBlue
Deal found 1/14$138
This Expedia deal was found by Cheapflights users on 1/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2810:00 am
ORD
-
BOS
Nonstop2h 20m
Multiple Airlines
Tue 3/36:00 am
BOS
-
ORD
1 stop11h 52m
Multiple Airlines
Deal found 1/14$139
This Cheapflightsfares deal was found by Cheapflights users on 1/14. 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.
Wed 2/1112:44 pm
ORD
-
BOS
1 stop9h 35m
Spirit Airlines
Wed 2/1811:31 am
BOS
-
ORD
1 stop13h 16m
Spirit Airlines
Deal found 1/14$141
This Expedia deal was found by Cheapflights users on 1/14. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1012:44 pm
ORD
-
BOS
1 stop9h 35m
Multiple Airlines
Thu 2/125:05 pm
BOS
-
ORD
1 stop7h 16m
Multiple Airlines
Deal found 1/14$142

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 January 15, 2026.
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

Wed 3/4

7:05 am-10:37 am

Nonstop2h 32m

Boston Logan Intl

Sun 3/8

7:25 am-9:35 am

Nonstop3h 10m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 2/4

11:05 am-2:30 pm

Nonstop2h 25m

Boston Logan Intl

Sun 2/8

6:00 am-8:04 am

Nonstop3h 04m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 1/31

2:00 pm-5:24 pm

Nonstop2h 24m

Boston Logan Intl

Tue 2/3

12:45 pm-2:50 pm

Nonstop3h 05m

$135

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 2/18

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Thu 2/26

7:00 am-9:10 am

Nonstop3h 10m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 2/10

2:00 pm-5:10 pm

Nonstop2h 10m

Boston Logan Intl

Wed 2/11

5:30 am-7:20 am

Nonstop2h 50m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 2/14

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Thu 2/26

7:00 am-9:10 am

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/12

6:22 pm-9:55 pm

Nonstop2h 33m

Boston Logan Intl

Wed 3/18

7:55 am-10:05 am

Nonstop3h 10m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/4

8:21 pm-11:56 pm

Nonstop2h 35m

Boston Logan Intl

Mon 6/8

5:30 pm-7:26 pm

Nonstop2h 56m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 2/25

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Sat 2/28

7:00 am-9:10 am

Nonstop3h 10m

$138

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 3/5

10:00 am-1:20 pm

Nonstop2h 20m

Boston Logan Intl

Sun 3/8

7:00 am-9:09 am

Nonstop3h 09m

$138

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/13

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, September is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $91). Flying from Chicago to Massachusetts in February is currently the most expensive (average of $132). 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 January 15, 2026.

One of the essential ways to save on airfare from Chicago to Massachusetts is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 46% on airfare.

What is the cheapest day to fly from Chicago to Massachusetts?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Massachusetts. Price data was last updated on January 10, 2026.

Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Saturday afternoons when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 January 15, 2026.

The most flights from CHI to USMA are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (18 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 January 15, 2026.
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
4,258 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,258 reviews
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,051 reviews
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,164 reviews
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,136 reviews
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
JetBlue
7.2
Good
2,887 reviews
Southwest
8.0
Very good
4,258 reviews

Boarding

8.1

Crew

8.6

Food

7.0

Entertainment

7.5

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Chicago to Massachusetts?

    There are many flights that can get you from Chicago to Massachusetts in 2h 20m. Fly via Delta, United Airlines, or JetBlue to get the fastest option. The distance between Chicago and Massachusetts is about 864 mi. All flights are typically nonstop.

  • 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 $55. However, be on the lookout for offers from JetBlue and United 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: Envoy Air (86%), Avianca (76%), United Airlines( 76%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $65. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $116 on average, our data indicates $764 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, September is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $91). Flying from Chicago to Massachusetts in February is currently the most expensive (average of $132). 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 6 airlines flying from Chicago to Massachusetts

Discover the top 6 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 January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$62Average$309FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$79Average$158FlexibilityNo cancel feeOn-time65%
DeltaCheapest$92Average$255FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$117Average$437FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$117Average$446FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$137Average$244FlexibilityNo cancel feeOn-time63%

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