HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$79+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
dic. 23 — dic. 301
lun. 12/23
lun. 12/30
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Massachusetts with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Massachusetts

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Massachusetts (USMA). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated diciembre 18, 2024.

Round-trip from

$113
(Kiwi.com)

One-way from

$79
(JetBlue)
From Chicago (CHI) to Massachusetts
Search Deals
One-way flight from Chicago (CHI) to Massachusetts
Search Deals

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 diciembre 18, 2024.

This FlightHub deal was found by Cheapflights users on 12/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/239:59 pmMDW - BOS
1 stop8h 02mFrontier
mar. 12/315:45 amBOS - MDW
1 stop10h 26mFrontier
Deal found 12/18$138
This American Airlines deal was found by Cheapflights users on 12/17. 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.
mié. 12/257:25 amORD - BOS
Nonstop2h 34mAmerican Airlines
mar. 1/76:00 amBOS - ORD
Nonstop3h 08mAmerican Airlines
Deal found 12/17$173
This Frontier deal was found by Cheapflights users on 12/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/2510:22 pmORD - BOS
1 stop8h 11mFrontier
mar. 1/76:00 amBOS - ORD
1 stop8h 34mFrontier
Deal found 12/17$178
This JetBlue deal was found by Cheapflights users on 12/17. 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.
mié. 12/258:42 amORD - BOS
Nonstop2h 29mJetBlue
jue. 1/26:00 amBOS - ORD
Nonstop3h 07mJetBlue
Deal found 12/17$194
This Kiwi.com deal was found by Cheapflights users on 12/17. 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. 12/241:24 pmORD - BOS
1 stop6h 56mMultiple Airlines
lun. 1/611:55 amBOS - ORD
1 stop12h 02mMultiple Airlines
Deal found 12/17$225
This United Airlines deal was found by Cheapflights users on 12/17. 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.
mié. 12/259:30 pmORD - BOS
Nonstop2h 24mUnited Airlines
mié. 1/15:45 amBOS - ORD
1 stop5h 10mUnited Airlines
Deal found 12/17$228
This Southwest deal was found by Cheapflights users on 12/17. 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.
mié. 12/256:25 pmMDW - BOS
Nonstop2h 10mSouthwest
dom. 1/56:25 amBOS - MDW
Nonstop2h 50mSouthwest
Deal found 12/17$230
This Delta deal was found by Cheapflights users on 12/18. 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.
mar. 12/245:57 pmORD - BOS
1 stop5h 53mDelta
mié. 1/83:30 pmBOS - ORD
Nonstop3h 06mDelta
Deal found 12/18$238
This CheapOair deal was found by Cheapflights users on 12/18. 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.
mié. 12/187:00 amORD - BOS
1 stop9h 26mSpirit Airlines
mar. 1/212:06 pmBOS - ORD
1 stop23h 51mSpirit Airlines
Deal found 12/18$249
This FlightHub deal was found by Cheapflights users on 12/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/238:25 amMDW - BDL
1 stop7h 40mFrontier
mié. 1/14:00 pmBDL - MDW
1 stop6h 17mFrontier
Deal found 12/18$268
This American Airlines deal was found by Cheapflights users on 12/17. 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.
mar. 12/315:02 amORD - ALB
1 stop4h 47mAmerican Airlines
mar. 1/73:00 pmALB - ORD
Nonstop2h 40mAmerican Airlines
Deal found 12/17$304
This eDestinos deal was found by Cheapflights users on 12/16. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/317:45 amMDW - BOS
1 stop27h 07mMultiple Airlines
dom. 1/59:34 amBOS - MDW
2 stops28h 50mMultiple Airlines
Deal found 12/16$310

Find flights from Chicago to Massachusetts within your budget

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 diciembre 18, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

lun. 1/6

10:59 am-12:44 am

1 stop12h 45m

Boston Logan Intl

mié. 1/8

1:05 pm-7:51 pm

1 stop7h 46m

$113

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 1/9

5:02 pm-12:30 am

1 stop6h 28m

Boston Logan Intl

lun. 1/13

11:37 am-10:23 pm

1 stop11h 46m

$114

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

mar. 1/7

5:24 pm-12:30 am

1 stop6h 06m

Boston Logan Intl

vie. 1/10

6:00 am-11:51 am

1 stop6h 51m

$116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 2/1

10:29 am-9:44 pm

1 stop10h 15m

Boston Logan Intl

mié. 2/5

6:25 am-4:10 pm

1 stop10h 45m

$144

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 1/9

2:35 pm-6:10 pm

Nonstop2h 35m

Boston Logan Intl

lun. 1/13

7:15 am-9:25 am

Nonstop3h 10m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 1/9

10:05 am-1:20 pm

Nonstop2h 15m

Boston Logan Intl

lun. 1/13

8:10 am-10:05 am

Nonstop2h 55m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 1/16

7:00 am-10:15 am

Nonstop2h 15m

Boston Logan Intl

dom. 1/19

11:28 am-3:44 pm

1 stop5h 16m

$166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 2/15

12:20 pm-3:38 pm

Nonstop2h 18m

Boston Logan Intl

mié. 2/19

3:00 pm-5:04 pm

Nonstop3h 04m

$183

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 1/9

7:32 pm-8:26 am

1 stop11h 54m

Boston Logan Intl

lun. 1/13

3:50 pm-4:14 pm

1 stop25h 24m

$193

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

sáb. 1/18

4:25 pm-2:02 pm

1 stop20h 37m

Worcester

sáb. 1/25

2:32 pm-10:47 am

1 stop21h 15m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 60 results
1
2
3
...
6

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.

Travel insights for flights from Chicago to Massachusetts

Get recent, data-driven insights about flights from Chicago to Massachusetts including ideal travel times, pricing trends, and more.

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 July is currently the most expensive (average of $311). 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 diciembre 18, 2024.

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.

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 diciembre 18, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Frontier, JetBlue and American Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,848 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,552 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,604 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Qatar Airways
7.5
Good
3,798 reviews
Southwest
8.1
Very good
4,848 reviews

Comfort

8.1

Overall

8.1

Entertainment

7.7

Boarding

8.2

Crew

8.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $79. However, be on the lookout for offers from Southwest and Frontier, 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 (94%), Royal Jordanian (91%), Etihad Airways( 90%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $78. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $95 on average our data indicates $577 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 July is currently the most expensive (average of $311). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Massachusetts

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Orlando flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Miami flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Newark flights
O'Hare Intl to Denver flights
O'Hare Intl to Tampa flights
Midway to Las Vegas flights
O'Hare Intl to Seattle flights
Midway to Dallas/Fort Worth flights
Midway to Miami flights
O'Hare Intl to Hobby flights
O'Hare Intl to Boston flights
Midway to Newark flights
Midway to Orlando flights
O'Hare Intl to Honolulu flights
Midway to John F Kennedy Intl flights
O'Hare Intl to Atlanta flights
O'Hare Intl to New Orleans flights
Midway to LaGuardia flights
O'Hare Intl to San Diego flights
Midway to Sky Harbor Intl flights
O'Hare Intl to George Bush Intcntl flights
Midway to Hobby flights
O'Hare Intl to Fort Myers flights
O'Hare Intl to San Francisco flights
Midway to Los Angeles flights
O'Hare Intl to Dulles Intl flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to West Palm Beach flights
O'Hare Intl to Austin flights
O'Hare Intl to Baltimore flights
Midway to Atlanta flights
Midway to Tampa flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Salt Lake City flights
O'Hare Intl to Burbank flights
O'Hare Intl to Ontario flights
O'Hare Intl to Philadelphia flights
St. Louis to Las Vegas flights
O'Hare Intl to Nashville flights
O'Hare Intl to Palm Springs flights
O'Hare Intl to Key West flights
O'Hare Intl to Sarasota flights
Midway to Denver flights

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 diciembre 18, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$315FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$116FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$84Average$556FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$138Average$440FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$149Average$387FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$275FlexibilityNo cancel feeOn-time63%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.