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$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 3/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
feb. 25 — mar. 41
mar. 2/25
mar. 3/4
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 febrero 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$153
(Mytrip)

One-way from

$79
(JetBlue)

Popular in

April

Cheapest in

September

Average price

$247

Good round-trip deal

$198 or less

Good one-way deal

$108 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. 14% potential increase in price ($42 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in February 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 febrero 20, 2025.

This Mytrip deal was found by Cheapflights users on 2/19. 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.
mié. 3/510:25 amORD - BOS
3 stops33h 55mSpirit Airlines
mié. 3/125:00 pmBOS - ORD
2 stops15h 44mSpirit Airlines
Deal found 2/19$151
This Booking.com deal was found by Cheapflights users on 2/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/13:25 pmORD - BOS
1 stop8h 05mMultiple Airlines
mié. 3/511:14 amBOS - ORD
1 stop13h 42mMultiple Airlines
Deal found 2/19$152
This KAYAK deal was found by Cheapflights users on 2/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/57:10 amORD - BOS
Nonstop2h 33mDelta
dom. 3/97:00 amBOS - ORD
Nonstop3h 09mDelta
Deal found 2/20$155
This Southwest deal was found by Cheapflights users on 2/19. 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.
jue. 5/17:20 pmMDW - BOS
Nonstop2h 15mSouthwest
dom. 5/48:20 pmBOS - MDW
Nonstop2h 40mSouthwest
Deal found 2/19$157
This American Airlines deal was found by Cheapflights users on 2/20. 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. 4/53:13 pmORD - BOS
Nonstop2h 24mAmerican Airlines
lun. 4/78:59 pmBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 2/20$158
This CheapOair deal was found by Cheapflights users on 2/20. 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. 3/72:41 pmMDW - BOS
1 stop16h 40mFrontier
sáb. 3/159:12 amBOS - MDW
1 stop14h 28mFrontier
Deal found 2/20$160
This Frontier deal was found by Cheapflights users on 2/19. 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.
jue. 2/274:21 pmORD - BOS
1 stop7h 23mFrontier
jue. 3/275:10 amBOS - ORD
1 stop6h 40mFrontier
Deal found 2/19$162
This JetBlue deal was found by Cheapflights users on 2/19. 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.
jue. 5/16:30 pmORD - BOS
Nonstop2h 29mJetBlue
dom. 5/46:00 amBOS - ORD
Nonstop3h 01mJetBlue
Deal found 2/19$167
This United Airlines deal was found by Cheapflights users on 2/19. 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.
jue. 4/37:10 amORD - BOS
Nonstop2h 28mUnited Airlines
dom. 4/67:43 amBOS - ORD
Nonstop2h 57mUnited Airlines
Deal found 2/19$168
This United Airlines deal was found by Cheapflights users on 2/19. 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. 4/211:20 amORD - ALB
Nonstop2h 06mUnited Airlines
mié. 4/96:00 amALB - ORD
Nonstop2h 31mUnited Airlines
Deal found 2/19$177
This Delta deal was found by Cheapflights users on 2/19. 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.
mié. 4/26:45 amORD - ALB
1 stop4h 09mDelta
mié. 4/95:30 amALB - ORD
1 stop4h 39mDelta
Deal found 2/19$197
This Southwest deal was found by Cheapflights users on 2/19. 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.
vie. 5/162:40 pmMDW - ALB
1 stop6h 25mSouthwest
lun. 5/197:30 amALB - MDW
Nonstop2h 10mSouthwest
Deal found 2/19$207

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 febrero 20, 2025.

Fly from

Chicago

Fly to

Massachusetts

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

mié. 3/5

10:25 am-9:20 pm

3 stops33h 55m

Boston Logan Intl

mié. 3/12

5:00 pm-7:44 am

2 stops15h 44m

$151

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 4/17

9:20 am-12:47 am

1 stop14h 27m

Boston Logan Intl

lun. 4/21

9:31 pm-8:04 am

1 stop11h 33m

$153

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

vie. 3/7

7:10 am-10:43 am

Nonstop2h 33m

Boston Logan Intl

lun. 3/10

7:25 am-9:34 am

Nonstop3h 09m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

jue. 5/1

7:20 pm-10:35 pm

Nonstop2h 15m

Boston Logan Intl

dom. 5/4

8:20 pm-10:00 pm

Nonstop2h 40m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

sáb. 4/5

3:13 pm-6:37 pm

Nonstop2h 24m

Boston Logan Intl

lun. 4/7

8:59 pm-10:57 pm

Nonstop2h 58m

$158

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

vie. 3/7

2:41 pm-8:21 am

1 stop16h 40m

Boston Logan Intl

sáb. 3/15

9:12 am-10:40 pm

1 stop14h 28m

$160

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

dom. 3/9

8:10 am-9:11 am

1 stop24h 01m

Boston Logan Intl

dom. 3/16

6:00 am-7:44 am

1 stop26h 44m

$162

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 3/6

7:30 am-10:49 am

Nonstop2h 19m

Boston Logan Intl

lun. 3/10

5:30 am-9:35 am

1 stop5h 05m

$164

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

jue. 5/1

6:30 pm-9:59 pm

Nonstop2h 29m

Boston Logan Intl

dom. 5/4

6:00 am-8:01 am

Nonstop3h 01m

$167

ChicagoAlbany

ORD - ALB

ORDALB

Chicago O'Hare Intl

mié. 4/2

11:20 am-2:26 pm

Nonstop2h 06m

Albany Intl

mié. 4/9

6:00 am-7:31 am

Nonstop2h 31m

$177

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

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 febrero 20, 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 febrero 20, 2025.

The most flights from CHI to USMA are scheduled on a Monday (57 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (20 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 febrero 20, 2025.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Southwest, Alaska Airlines and Delta. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,766 reviews
Southwest
8.1
Very good
4,411 reviews

Entertainment

7.6

Crew

8.7

Food

7.1

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 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: WestJet (100%), Air France (100%), Korean Air( 91%).

  • 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 $91 on average our data indicates $680 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.

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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 febrero 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$302FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$85Average$464FlexibilityNo cancel feeOn-time62%
FrontierCheapest$86Average$113FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$139Average$422FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$156Average$447FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$157Average$278FlexibilityNo cancel feeOn-time63%
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