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$47+ 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jan 2 — Jan 91
Fri 1/2
Fri 1/9
1 adult, Economy
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Cheap 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 December 3, 2025.

This JetBlue deal was found by Cheapflights users on 12/2. 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.
Thu 12/187:41 pmORD - BOS
Nonstop2h 29mJetBlue
Sat 1/173:35 pmBOS - ORD
Nonstop3h 08mJetBlue
Deal found 12/2$119
This American Airlines deal was found by Cheapflights users on 12/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/156:10 amORD - BOS
Nonstop2h 25mAmerican Airlines
Thu 1/16:36 amBOS - ORD
Nonstop3h 11mAmerican Airlines
Deal found 12/2$122
This JetBlue deal was found by Cheapflights users on 12/2. 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.
Thu 12/257:41 pmORD - BOS
Nonstop2h 29mJetBlue
Tue 12/304:31 pmBOS - ORD
Nonstop3h 15mJetBlue
Deal found 12/2$124
This Southwest deal was found by Cheapflights users on 12/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/256:15 pmMDW - BOS
Nonstop2h 20mSouthwest
Fri 1/25:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/1$124
This Trip.com deal was found by Cheapflights users on 12/1. 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.
Thu 12/118:38 pmORD - BOS
Nonstop2h 28mJetBlue
Sun 12/148:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 12/1$125
This JetBlue deal was found by Cheapflights users on 12/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/128:38 pmORD - BOS
Nonstop2h 28mJetBlue
Sun 12/148:30 amBOS - ORD
Nonstop3h 05mJetBlue
Deal found 12/1$127
This Southwest deal was found by Cheapflights users on 12/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/135:35 pmMDW - BOS
Nonstop2h 15mSouthwest
Sun 12/145:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/1$127
This JetBlue deal was found by Cheapflights users on 12/2. 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.
Fri 12/267:41 pmORD - BOS
Nonstop2h 29mJetBlue
Sat 1/35:00 pmBOS - ORD
Nonstop3h 20mJetBlue
Deal found 12/2$131
This Southwest deal was found by Cheapflights users on 12/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/265:30 amMDW - BOS
Nonstop2h 15mSouthwest
Fri 1/25:15 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 12/1$131
This United Airlines deal was found by Cheapflights users on 11/30. 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 12/136:17 pmORD - BOS
Nonstop2h 28mUnited Airlines
Mon 1/129:30 amBOS - ORD
Nonstop3h 04mUnited Airlines
Deal found 11/30$132
This Kiwi.com deal was found by Cheapflights users on 11/30. 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 12/131:24 pmORD - BOS
1 stop19h 58mMultiple Airlines
Mon 1/1211:41 amBOS - ORD
1 stop9h 00mMultiple Airlines
Deal found 11/30$134
This Kiwi.com deal was found by Cheapflights users on 12/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:05 amORD - BOS
1 stop18h 09mFrontier
Tue 1/66:00 amBOS - ORD
1 stop7h 54mFrontier
Deal found 12/1$135

Find flight deals from Chicago to Massachusetts

Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated December 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$117
(Delta)

One-way from

$47
(United Airlines)

Popular in

April

Cheapest in

September

Average price

$252

Good round-trip deal

$131 or less

Good one-way deal

$65 or less
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago (CHI) to Massachusetts
Search Deals
One-way flight from Chicago (CHI) to Massachusetts
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Massachusetts.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Massachusetts.
Search Deals

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 December 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

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/23

2:25 pm-5:54 pm

Nonstop2h 29m

Boston Logan Intl

Thu 1/29

7:30 am-9:41 am

Nonstop3h 11m

$122

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 12/25

6:15 pm-9:35 pm

Nonstop2h 20m

Boston Logan Intl

Fri 1/2

5:15 am-7:00 am

Nonstop2h 45m

$124

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 12/12

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

Sun 12/14

6:00 am-8:00 am

Nonstop3h 00m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/8

6:15 am-2:05 pm

1 stop6h 50m

Boston Logan Intl

Mon 1/12

7:55 pm-10:01 pm

Nonstop3h 06m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/3

2:25 pm-5:54 pm

Nonstop2h 29m

Boston Logan Intl

Mon 2/9

6:35 pm-11:56 pm

1 stop6h 21m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/30

2:25 pm-5:54 pm

Nonstop2h 29m

Boston Logan Intl

Sat 1/31

5:29 am-9:41 am

1 stop5h 12m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/17

10:11 am-1:35 pm

Nonstop2h 24m

Boston Logan Intl

Tue 2/24

3:50 pm-5:53 pm

Nonstop3h 03m

$127

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/22

10:29 am-3:53 pm

1 stop4h 24m

Boston Logan Intl

Sat 1/31

5:15 pm-7:26 pm

Nonstop3h 11m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 1/20

10:45 am-4:23 pm

1 stop4h 38m

Boston Logan Intl

Wed 1/28

4:10 pm-6:19 pm

Nonstop3h 09m

$128

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 1/21

10:29 am-3:53 pm

1 stop4h 24m

Boston Logan Intl

Tue 1/27

11:30 am-1:39 pm

Nonstop3h 09m

$128

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

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, 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 $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 December 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 64% 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 29, 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 December 3, 2025.

The most flights from CHI to USMA are scheduled on a Tuesday (54 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (23 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 December 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
4,253 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
United Airlines
7.4
Good
9,063 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.2
Good
11,045 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
JetBlue
7.2
Good
2,901 reviews
Southwest
8.0
Very good
4,253 reviews

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

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, Southwest, 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 Frontier, with whom users have recently found tickets for as low as $50. However, be on the lookout for offers from Spirit Airlines and JetBlue, 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 (79%), JetBlue (76%), Hawaiian Airlines( 76%).

  • 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 $91 on average, our data indicates $634 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 $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 December 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$79Average$318FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$83Average$166FlexibilityNo cancel feeOn-time65%
DeltaCheapest$103Average$259FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$104Average$115FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$117Average$446FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$117Average$441FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$135Average$249FlexibilityNo cancel feeOn-time63%

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