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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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$59
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$230

Good round-trip deal

$150 or less

Good one-way deal

$93 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 ($14 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 November 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 November 3, 2025.

This United Airlines deal was found by Cheapflights users on 11/3. 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.
Thu 11/276:15 amORD - BOS
Nonstop2h 15mUnited Airlines
Wed 12/312:50 pmBOS - ORD
Nonstop3h 00mUnited Airlines
Deal found 11/3$117
This Southwest deal was found by Cheapflights users on 11/3. 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 12/36:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Wed 12/101:35 pmBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/3$117
This Delta deal was found by Cheapflights users on 11/3. 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 12/47:10 amORD - BOS
Nonstop2h 26mDelta
Sun 12/77:30 amBOS - ORD
Nonstop3h 03mDelta
Deal found 11/3$118
This Trip.com deal was found by Cheapflights users on 11/1. 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.
Fri 11/146:55 pmORD - BOS
Nonstop2h 32mJetBlue
Tue 11/188:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/1$120
This JetBlue deal was found by Cheapflights users on 11/3. 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.
Wed 11/268:45 pmORD - BOS
Nonstop2h 28mJetBlue
Sat 12/68:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/3$122
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Wed 12/311:25 amORD - BOS
Nonstop2h 24mJetBlue
Thu 1/14:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 11/2$124
This Southwest deal was found by Cheapflights users on 11/2. 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 12/246:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Sun 12/285:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/2$124
This Trip.com deal was found by Cheapflights users on 11/3. 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 11/1211:20 amORD - BOS
Nonstop2h 24mJetBlue
Tue 11/188:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 11/3$125
This Cheapflightsfares deal was found by Cheapflights users on 11/3. 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 12/33:43 pmORD - BOS
1 stop7h 10mSpirit Airlines
Wed 12/1010:56 amBOS - ORD
1 stop11h 52mSpirit Airlines
Deal found 11/3$126
This Delta deal was found by Cheapflights users on 11/3. 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 11/247:10 amORD - BOS
Nonstop2h 25mDelta
Sat 12/67:30 amBOS - ORD
Nonstop3h 03mDelta
Deal found 11/3$127
This Southwest deal was found by Cheapflights users on 11/2. 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.
Thu 12/46:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Tue 12/96:00 pmBOS - MDW
1 stop5h 35mSouthwest
Deal found 11/2$127
This Priceline deal was found by Cheapflights users on 11/3. 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 12/76:00 amORD - BOS
1 stop5h 02mFrontier
Thu 12/1111:28 amBOS - ORD
1 stop6h 59mFrontier
Deal found 11/3$128

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 November 3, 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

Wed 12/10

1:30 pm-4:45 pm

Nonstop2h 15m

Boston Logan Intl

Sat 12/13

5:20 am-7:05 am

Nonstop2h 45m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 12/4

7:10 am-10:36 am

Nonstop2h 26m

Boston Logan Intl

Sun 12/7

7:52 pm-9:47 pm

Nonstop2h 55m

$118

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/24

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/28

5:15 am-7:00 am

Nonstop2h 45m

$124

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 11/8

1:55 pm-5:15 pm

Nonstop2h 20m

Boston Logan Intl

Thu 11/13

9:40 am-11:40 am

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 11/24

7:10 am-10:35 am

Nonstop2h 25m

Boston Logan Intl

Thu 12/4

4:05 pm-6:02 pm

Nonstop2h 57m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 11/13

7:15 am-10:34 am

Nonstop2h 19m

Boston Logan Intl

Sat 11/15

6:23 pm-8:23 pm

Nonstop3h 00m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/4

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sun 12/7

6:50 pm-11:30 pm

1 stop5h 40m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Sat 11/15

9:50 am-1:10 pm

Nonstop2h 20m

Boston Logan Intl

Sat 11/15

4:45 pm-6:30 pm

Nonstop2h 45m

$127

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 12/23

7:50 pm-11:05 pm

Nonstop2h 15m

Boston Logan Intl

Sat 12/27

5:20 am-7:05 am

Nonstop2h 45m

$131

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/25

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Sat 1/3

6:55 pm-11:20 pm

1 stop5h 25m

$134

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

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 $137). 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 November 3, 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 November 2, 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 November 3, 2025.

The most flights from CHI to USMA are scheduled on a Monday (70 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 on average).

How much does it cost to fly round-trip from Chicago to Massachusetts?

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 November 3, 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
4,238 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
7.9
Good
8,002 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
8,997 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
11,038 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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
2,907 reviews
Southwest
8.0
Very good
4,238 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

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 15m. Fly via Southwest, Delta, or United Airlines to get the fastest option. The distance between Chicago and Massachusetts is about 857 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 JetBlue, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from United Airlines 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?

    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 (81%), Etihad Airways (72%), Virgin Atlantic( 71%).

  • 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 $115 on average, our data indicates $966 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 $137). 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$68Average$151FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$76Average$322FlexibilityNo cancel feeOn-time62%
DeltaCheapest$102Average$262FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$442FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$118Average$450FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$137Average$250FlexibilityNo cancel feeOn-time63%

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