HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Massachusetts

$74+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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

Keep the following information in mind while searching for Chicago to Massachusetts flight deals. Data was last updated April 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$116
(Southwest)

One-way from

$74
(JetBlue Airways)

Popular in

April

Cheapest in

September

Average price

$293

Good round-trip deal

$191 or less

Good one-way deal

$78 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. 14% potential increase in price ($41 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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

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 April 2, 2025.

This Southwest deal was found by Cheapflights users on 4/1. 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.
Wed 5/71:50 pmORD - BOS
1 stop4h 20mSouthwest
Sun 5/115:45 amBOS - ORD
1 stop7h 05mSouthwest
Deal found 4/1$116
This Southwest deal was found by Cheapflights users on 4/1. 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.
Wed 4/306:50 amMDW - BOS
1 stop6h 10mSouthwest
Sat 5/34:15 pmBOS - MDW
1 stop7h 15mSouthwest
Deal found 4/1$116
This JetBlue deal was found by Cheapflights users on 4/1. 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.
Wed 5/77:31 pmORD - BOS
Nonstop2h 29mJetBlue
Tue 5/134:30 pmBOS - ORD
Nonstop3h 06mJetBlue
Deal found 4/1$117
This Cheapflightsfares deal was found by Cheapflights users on 4/1. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/1312:41 pmORD - BOS
1 stop9h 48mSpirit Airlines
Wed 5/143:49 pmBOS - ORD
1 stop8h 15mSpirit Airlines
Deal found 4/1$118
This American Airlines deal was found by Cheapflights users on 4/2. 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.
Tue 5/134:40 pmORD - BOS
Nonstop2h 21mAmerican Airlines
Wed 5/146:35 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/2$119
This United Airlines deal was found by Cheapflights users on 4/1. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/226:30 amORD - BOS
Nonstop2h 26mUnited Airlines
Sun 8/317:30 pmBOS - ORD
1 stop5h 12mUnited Airlines
Deal found 4/1$123
This American Airlines deal was found by Cheapflights users on 3/31. 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.
Wed 4/165:10 pmORD - ORH
1 stop19h 15mAmerican Airlines
Sun 4/202:18 pmORH - ORD
1 stop21h 47mAmerican Airlines
Deal found 3/31$154
This CheapOair deal was found by Cheapflights users on 4/2. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/14:15 pmORD - BOS
1 stop7h 50mMultiple Airlines
Thu 5/85:42 pmBOS - ORD
1 stop6h 47mMultiple Airlines
Deal found 4/2$191
This Frontier deal was found by Cheapflights users on 4/1. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/81:19 pmMDW - BOS
1 stop10h 46mFrontier
Mon 5/1212:58 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 4/1$198
This Delta deal was found by Cheapflights users on 4/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/27:00 amORD - BOS
Nonstop2h 25mDelta
Wed 6/47:15 amBOS - ORD
Nonstop2h 54mDelta
Deal found 4/1$210
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/249:25 amORD - ORH
1 stop4h 46mDelta
Wed 7/23:55 pmORH - ORD
1 stop7h 24mDelta
Deal found 4/2$212
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/229:25 amORD - ACK
1 stop4h 52mDelta
Tue 7/294:15 pmACK - ORD
1 stop7h 31mDelta
Deal found 4/2$222

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 April 2, 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

Wed 5/7

1:50 pm-7:10 pm

1 stop4h 20m

Boston Logan Intl

Sun 5/11

5:45 am-11:50 am

1 stop7h 05m

$116

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 4/30

6:50 am-2:00 pm

1 stop6h 10m

Boston Logan Intl

Sat 5/3

4:15 pm-10:30 pm

1 stop7h 15m

$116

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/7

7:31 pm-11:00 pm

Nonstop2h 29m

Boston Logan Intl

Tue 5/13

4:30 pm-6:36 pm

Nonstop3h 06m

$117

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/13

12:41 pm-11:29 pm

1 stop9h 48m

Boston Logan Intl

Wed 5/14

3:49 pm-11:04 pm

1 stop8h 15m

$118

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/13

4:40 pm-8:01 pm

Nonstop2h 21m

Boston Logan Intl

Wed 5/14

6:35 am-8:31 am

Nonstop2h 56m

$119

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/8

12:50 pm-4:17 pm

Nonstop2h 27m

Boston Logan Intl

Wed 8/20

7:30 pm-11:42 pm

1 stop5h 12m

$123

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 4/16

5:10 pm-1:25 pm

1 stop19h 15m

Worcester

Sun 4/20

2:18 pm-11:05 am

1 stop21h 47m

$154

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/1

4:15 pm-1:05 am

1 stop7h 50m

Boston Logan Intl

Thu 5/8

3:49 pm-12:05 am

1 stop9h 16m

$191

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/8

1:19 pm-1:05 am

1 stop10h 46m

Boston Logan Intl

Mon 5/12

12:58 pm-11:47 pm

1 stop11h 49m

$198

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 6/2

7:00 am-10:25 am

Nonstop2h 25m

Boston Logan Intl

Wed 6/4

7:15 am-9:09 am

Nonstop2h 54m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

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.

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 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 April 2, 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 April 2, 2025.

The most flights from CHI to USMA are scheduled on a Wednesday (64 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (13 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 April 2, 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
9,827 reviews

Entertainment

7.1

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Alaska Airlines
8.0
Very good
9,827 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Southwest
8.0
Very good
4,274 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Delta
8.0
Very good
7,897 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Avelo Airlines
7.5
Good
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Qatar Airways
7.4
Good
3,540 reviews
Alaska Airlines
8.0
Very good
9,827 reviews

Entertainment

7.1

Food

7.1

Comfort

7.9

Crew

8.5

Boarding

8.2

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $74. However, be on the lookout for offers from Southwest and Spirit 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: Air France (100%), Iberia (88%), Virgin Atlantic( 87%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $52. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $97 on average our data indicates $443 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 John F Kennedy Intl flights
O'Hare Intl to Las Vegas flights
O'Hare Intl to Dallas/Fort Worth flights
O'Hare Intl to LaGuardia flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Newark flights
O'Hare Intl to Miami flights
O'Hare Intl to Seattle flights
O'Hare Intl to Los Angeles flights
O'Hare Intl to Denver flights
O'Hare Intl to Fort Lauderdale flights
O'Hare Intl to Orlando flights
O'Hare Intl to Dulles Intl flights
Midway to John F Kennedy Intl flights
Midway to Newark flights
O'Hare Intl to Atlanta flights
O'Hare Intl to San Francisco flights
O'Hare Intl to Boston flights
O'Hare Intl to Reagan-National flights
O'Hare Intl to San Diego flights
O'Hare Intl to Honolulu flights
O'Hare Intl to Tampa flights
O'Hare Intl to Santa Ana flights
O'Hare Intl to Austin flights
Midway to Las Vegas flights
O'Hare Intl to Baltimore flights
O'Hare Intl to New Orleans flights
O'Hare Intl to Philadelphia flights
O'Hare Intl to Ontario flights
O'Hare Intl to Nashville flights
O'Hare Intl to Fort Myers flights
St. Louis to Seattle flights
O'Hare Intl to Portland flights
O'Hare Intl to Salt Lake City flights
Midway to LaGuardia flights
St. Louis to Las Vegas flights
Midway to Atlanta flights
O'Hare Intl to Burbank flights
O'Hare Intl to Charleston flights
O'Hare Intl to Charlotte flights
O'Hare Intl to San Antonio flights
Midway to Dallas/Fort Worth flights
O'Hare Intl to Hobby flights
O'Hare Intl to Savannah flights
Midway to Seattle flights
Midway to Miami flights
O'Hare Intl to Raleigh flights
Midway to Dulles Intl flights
O'Hare Intl to George Bush Intcntl flights
Midway to Hobby 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$301FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$115FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$82Average$494FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$140Average$427FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$153Average$388FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$292FlexibilityNo 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.