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$67+ 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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$127
(Delta)

One-way from

$67
(CheapOair)

Popular in

April

Cheapest in

September

Average price

$244

Good round-trip deal

$167 or less

Good one-way deal

$102 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. 5% potential increase in price ($13 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 14, 2025.

This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/207:10 amORD - BOS
Nonstop2h 25mDelta
Fri 12/57:52 pmBOS - ORD
Nonstop2h 55mDelta
Deal found 10/13$127
This Southwest deal was found by Cheapflights users on 10/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/75:15 pmMDW - BOS
1 stop4h 40mSouthwest
Mon 11/106:55 pmBOS - MDW
Nonstop2h 50mSouthwest
Deal found 10/12$127
This Southwest deal was found by Cheapflights users on 10/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2510:00 amMDW - BOS
2 stops7h 50mSouthwest
Tue 10/285:15 amBOS - MDW
Nonstop2h 40mSouthwest
Deal found 10/13$132
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/99:20 amORD - BOS
Nonstop2h 24mUnited Airlines
Sun 11/167:30 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/13$133
This Southwest deal was found by Cheapflights users on 10/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/56:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sat 11/87:25 amBOS - MDW
1 stop8h 55mSouthwest
Deal found 10/12$133
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/266:15 amORD - BOS
Nonstop2h 15mUnited Airlines
Thu 10/309:40 amBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 10/13$135
This Delta deal was found by Cheapflights users on 10/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2810:25 amORD - BOS
Nonstop2h 30mDelta
Tue 10/287:30 pmBOS - ORD
Nonstop2h 49mDelta
Deal found 10/13$137
This Trip.com deal was found by Cheapflights users on 10/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/611:20 amORD - BOS
Nonstop2h 24mJetBlue
Sun 11/98:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/12$138
This Trip.com deal was found by Cheapflights users on 10/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2310:08 amORD - BOS
Nonstop2h 29mJetBlue
Wed 11/58:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 10/12$139
This United Airlines deal was found by Cheapflights users on 10/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/267:15 amORD - BOS
Nonstop2h 19mUnited Airlines
Tue 10/2810:25 amBOS - ORD
1 stop7h 40mUnited Airlines
Deal found 10/13$140
This Kiwi.com deal was found by Cheapflights users on 10/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/116:00 amMDW - BOS
1 stop17h 44mFrontier
Sun 12/146:00 amBOS - MDW
1 stop13h 04mFrontier
Deal found 10/12$140
This American Airlines deal was found by Cheapflights users on 10/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/28:28 pmORD - BOS
Nonstop2h 24mAmerican Airlines
Wed 12/37:00 amBOS - ORD
Nonstop3h 25mAmerican Airlines
Deal found 10/12$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 October 14, 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

MDW - BOS

MDWBOS

Chicago Midway

Fri 11/7

2:55 pm-11:15 pm

1 stop7h 20m

Boston Logan Intl

Mon 11/10

6:55 pm-8:45 pm

Nonstop2h 50m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 10/31

4:55 pm-8:10 pm

Nonstop2h 15m

Boston Logan Intl

Tue 11/4

12:20 pm-5:50 pm

1 stop6h 30m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 11/9

9:20 am-12:44 pm

Nonstop2h 24m

Boston Logan Intl

Sun 11/16

7:30 am-9:30 am

Nonstop3h 00m

$133

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 10/28

10:25 am-1:55 pm

Nonstop2h 30m

Boston Logan Intl

Tue 10/28

7:30 pm-9:19 pm

Nonstop2h 49m

$137

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/5

12:55 pm-9:05 pm

1 stop7h 10m

Boston Logan Intl

Sat 11/8

9:20 am-6:30 pm

1 stop10h 10m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 10/25

10:00 am-6:50 pm

2 stops7h 50m

Boston Logan Intl

Tue 10/28

5:40 pm-10:05 pm

1 stop5h 25m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 11/5

12:55 pm-9:05 pm

1 stop7h 10m

Boston Logan Intl

Sun 11/9

6:50 am-3:40 pm

1 stop9h 50m

$142

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 11/6

9:35 am-5:15 pm

1 stop6h 40m

Boston Logan Intl

Sun 11/9

6:50 am-3:40 pm

1 stop9h 50m

$142

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/23

9:20 pm-12:50 am

Nonstop2h 30m

Boston Logan Intl

Wed 11/5

6:00 am-8:00 am

Nonstop3h 00m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 10/24

7:13 pm-10:46 pm

Nonstop2h 33m

Boston Logan Intl

Tue 10/28

3:55 pm-5:55 pm

Nonstop3h 00m

$147

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

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, November is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $71). Flying from Chicago to Massachusetts in February is currently the most expensive (average of $138). 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 October 14, 2025.

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 63% 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 October 5, 2025.

Travelers seeking maximum savings on their Chicago to Massachusetts flight should consider departing on Tuesday evenings 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 October 14, 2025.

The most flights from CHI to USMA are scheduled on a Sunday (79 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (51 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 October 14, 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
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,235 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,973 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,974 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,045 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
JetBlue
7.2
Good
2,904 reviews
Southwest
8.0
Very good
4,235 reviews

Entertainment

7.5

Overall

8.0

Food

7.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 24m. Fly via Southwest, United Airlines, or Delta to get the fastest option. The distance between Chicago and Massachusetts is about 864 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 United Airlines, with whom users have recently found tickets for as low as $69. However, be on the lookout for offers from Southwest and American 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 (91%), TAP AIR PORTUGAL (84%), Icelandair( 81%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $58. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $112 on average, our data indicates $540 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, November is the cheapest month in which you can book a flight from Chicago to Massachusetts (average of $71). Flying from Chicago to Massachusetts in February is currently the most expensive (average of $138). 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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$56Average$163FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$78Average$322FlexibilityNo cancel feeOn-time62%
DeltaCheapest$97Average$261FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$100Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$118Average$446FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$126Average$401FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$137Average$253FlexibilityNo cancel feeOn-time63%

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