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$62+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$121
(Kiwi.com)

One-way from

$62
(JetBlue)

Popular in

April

Cheapest in

August

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. 9% potential increase in price ($22 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 June 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 junio 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
mar. 7/85:05 amORD - BOS
1 stop9h 32mSpirit Airlines
mié. 7/98:39 pmBOS - ORD
1 stop13h 16mSpirit Airlines
Deal found 6/11$121
This Southwest deal was found by Cheapflights users on 6/12. 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.
dom. 9/215:55 amMDW - BOS
Nonstop2h 15mSouthwest
mié. 9/245:40 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 6/12$123
This American Airlines deal was found by Cheapflights users on 6/11. 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.
sáb. 8/98:25 pmORD - BOS
Nonstop2h 34mAmerican Airlines
mar. 8/125:29 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 6/11$125
This JetBlue deal was found by Cheapflights users on 6/9. 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.
vie. 9/266:50 pmORD - BOS
Nonstop2h 33mJetBlue
dom. 9/287:00 amBOS - ORD
Nonstop2h 57mJetBlue
Deal found 6/9$131
This Southwest deal was found by Cheapflights users on 6/12. 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.
dom. 9/217:30 amORD - BOS
1 stop9h 25mSouthwest
mié. 9/245:20 amBOS - ORD
1 stop8h 25mSouthwest
Deal found 6/12$142
This United Airlines deal was found by Cheapflights users on 6/10. 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.
vie. 8/229:15 pmORD - BOS
Nonstop2h 30mUnited Airlines
dom. 8/247:45 amBOS - ORD
Nonstop2h 56mUnited Airlines
Deal found 6/10$149
This Trip.com deal was found by Cheapflights users on 6/12. 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.
mar. 7/86:20 pmORD - BOS
Nonstop2h 39mMultiple Airlines
mié. 7/98:39 pmBOS - ORD
1 stop13h 16mMultiple Airlines
Deal found 6/12$163
This American Airlines deal was found by Cheapflights users on 6/10. 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.
jue. 9/259:37 pmORD - ORH
1 stop17h 14mAmerican Airlines
mié. 10/14:24 pmORH - ORD
2 stops15h 27mAmerican Airlines
Deal found 6/10$164
This Delta deal was found by Cheapflights users on 6/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/187:10 pmORD - BOS
Nonstop2h 40mDelta
mar. 7/227:20 amBOS - ORD
Nonstop2h 58mDelta
Deal found 6/11$173
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/86:16 amORD - ACK
1 stop4h 37mJetBlue
mar. 7/154:18 pmACK - ORD
1 stop7h 10mJetBlue
Deal found 6/11$192
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/12:46 pmMDW - BOS
1 stop16h 29mAllegiant Air
dom. 8/311:31 amBOS - MDW
1 stop20h 42mAllegiant Air
Deal found 6/11$200
This CheapOair deal was found by Cheapflights users on 6/9. 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.
vie. 8/299:17 amMDW - BOS
1 stop25h 51mFrontier
dom. 9/79:18 amBOS - MDW
1 stop23h 21mFrontier
Deal found 6/9$204

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 junio 12, 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

mar. 7/8

5:05 am-3:37 pm

1 stop9h 32m

Boston Logan Intl

mié. 7/9

8:39 pm-8:55 am

1 stop13h 16m

$121

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 8/9

8:25 pm-11:59 pm

Nonstop2h 34m

Boston Logan Intl

mar. 8/12

5:29 am-7:25 am

Nonstop2h 56m

$125

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

mar. 8/19

6:10 pm-9:35 pm

Nonstop2h 25m

Boston Logan Intl

jue. 8/21

5:15 am-6:45 am

Nonstop2h 30m

$125

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 8/8

5:51 pm-9:26 pm

Nonstop2h 35m

Boston Logan Intl

lun. 8/11

6:00 am-7:55 am

Nonstop2h 55m

$131

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 7/10

7:45 pm-11:12 pm

Nonstop2h 27m

Boston Logan Intl

lun. 7/14

8:20 pm-10:12 pm

Nonstop2h 52m

$137

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 9/5

2:55 pm-10:35 pm

1 stop6h 40m

Boston Logan Intl

lun. 9/8

10:45 am-4:25 pm

1 stop6h 40m

$145

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mar. 7/8

6:20 pm-9:59 pm

Nonstop2h 39m

Boston Logan Intl

mié. 7/9

8:39 pm-8:55 am

1 stop13h 16m

$163

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

jue. 9/25

9:37 pm-3:51 pm

1 stop17h 14m

Worcester

mié. 10/1

4:24 pm-6:51 am

2 stops15h 27m

$164

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 7/18

7:10 pm-10:50 pm

Nonstop2h 40m

Boston Logan Intl

mar. 7/22

7:20 am-9:18 am

Nonstop2h 58m

$173

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

mar. 7/8

6:16 am-11:53 am

1 stop4h 37m

Nantucket Memorial

mar. 7/15

4:18 pm-10:28 pm

1 stop7h 10m

$192

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

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, 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 June is currently the most expensive (average of $306). 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 junio 12, 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 junio 12, 2025.

The most flights from CHI to USMA are scheduled on a Thursday (80 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (19 on average).

Rainfall in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Massachusetts ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Massachusetts when rainfall is around 3.1 in.

Temperature in Massachusetts by month

Plan your trip to Massachusetts by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Massachusetts, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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 junio 12, 2025.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Alaska Airlines, Southwest and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
Delta
8.0
Very good
7,950 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
JetBlue
7.3
Good
2,925 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Entertainment

7.1

Crew

8.5

Overall

8.0

Comfort

7.8

Boarding

8.1

Food

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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 JetBlue, with whom users have recently found tickets for as low as $62. However, be on the lookout for offers from United Airlines and Southwest, 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 - Albany 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 (89%), TAP AIR PORTUGAL (84%), EL AL( 84%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $59. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $119 on average our data indicates $391 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 June is currently the most expensive (average of $306). 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.

See more FAQs

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$36Average$93FlexibilityNo cancel feeOn-time65%
FrontierCheapest$69Average$111FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$79Average$469FlexibilityNo cancel feeOn-time62%
DeltaCheapest$89Average$262FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$127Average$407FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$131Average$399FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$156Average$291FlexibilityNo cancel feeOn-time63%

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