Massachusetts

$55+ 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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Jan 21 — Jan 281
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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 January 16, 2025.

Round-trip from

$154
(Booking.com)

One-way from

$55
(Frontier)
From Chicago (CHI) to Massachusetts
One-way flight from Chicago (CHI) to Massachusetts

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 January 16, 2025.

This Mytrip deal was found by Cheapflights users on 1/14. 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.
Sat 2/15:50 amORD - BOS
3 stops25h 36mSpirit Airlines
Wed 2/56:25 amBOS - ORD
1 stop10h 45mSpirit Airlines
Deal found 1/14$154
This Kiwi.com deal was found by Cheapflights users on 1/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2412:25 pmORD - BOS
1 stop10h 10mMultiple Airlines
Fri 1/3111:46 amBOS - ORD
1 stop9h 59mMultiple Airlines
Deal found 1/16$155
This Flightnetwork deal was found by Cheapflights users on 1/15. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/115:31 pmMDW - BOS
1 stop6h 08mFrontier
Wed 2/126:00 amBOS - MDW
1 stop18h 00mFrontier
Deal found 1/15$156
This JetBlue deal was found by Cheapflights users on 1/15. 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 2/67:00 amORD - BOS
Nonstop2h 15mJetBlue
Tue 2/113:52 pmBOS - ORD
Nonstop3h 03mJetBlue
Deal found 1/15$157
This Southwest deal was found by Cheapflights users on 1/14. 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 1/2910:05 amMDW - BOS
Nonstop2h 15mSouthwest
Sun 2/27:00 amBOS - MDW
Nonstop2h 55mSouthwest
Deal found 1/14$157
This American Airlines deal was found by Cheapflights users on 1/15. 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.
Thu 2/612:30 pmORD - BOS
Nonstop2h 19mAmerican Airlines
Sun 2/96:00 amBOS - ORD
Nonstop3h 08mAmerican Airlines
Deal found 1/15$158
This Kissandfly.com deal was found by Cheapflights users on 1/15. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/64:41 pmORD - BOS
1 stop6h 58mFrontier
Sun 2/97:15 amBOS - ORD
Nonstop3h 06mFrontier
Deal found 1/15$162
This Delta deal was found by Cheapflights users on 1/15. 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.
Fri 3/1410:55 amORD - BOS
Nonstop2h 17mDelta
Sun 3/167:00 amBOS - ORD
Nonstop3h 09mDelta
Deal found 1/15$207
This United Airlines deal was found by Cheapflights users on 1/15. 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 1/2410:35 amORD - BOS
Nonstop2h 26mUnited Airlines
Thu 1/306:00 amBOS - ORD
Nonstop3h 03mUnited Airlines
Deal found 1/15$212
This American Airlines deal was found by Cheapflights users on 1/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/134:14 pmORD - ORH
1 stop20h 29mAmerican Airlines
Mon 2/172:15 pmORH - ORD
1 stop21h 30mAmerican Airlines
Deal found 1/16$253
This United Airlines deal was found by Cheapflights users on 1/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/1011:10 amORD - ALB
Nonstop2h 16mUnited Airlines
Wed 2/124:30 pmALB - ORD
Nonstop2h 52mUnited Airlines
Deal found 1/16$258
This American Airlines deal was found by Cheapflights users on 1/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/209:20 amORD - ALB
Nonstop2h 03mAmerican Airlines
Sat 2/223:00 pmALB - ORD
Nonstop2h 36mAmerican Airlines
Deal found 1/16$260

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 January 16, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 3/7

5:05 am-8:12 am

1 stop26h 07m

Boston Logan Intl

Tue 3/11

6:00 am-10:57 am

1 stop29h 57m

$154

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Mon 3/3

12:43 pm-12:44 am

1 stop11h 01m

Boston Logan Intl

Fri 3/7

10:41 am-9:25 pm

1 stop11h 44m

$154

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 2/6

7:00 am-10:15 am

Nonstop2h 15m

Boston Logan Intl

Mon 2/10

3:52 pm-5:55 pm

Nonstop3h 03m

$157

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 1/31

10:02 pm-12:27 am

1 stop25h 25m

Boston Logan Intl

Sun 2/2

6:25 am-4:10 pm

1 stop10h 45m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 2/11

3:56 pm-9:13 am

1 stop16h 17m

Boston Logan Intl

Thu 2/13

5:45 am-9:33 pm

2 stops16h 48m

$164

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Tue 2/4

6:25 pm-9:40 pm

Nonstop2h 15m

Boston Logan Intl

Tue 2/11

5:40 pm-7:30 pm

Nonstop2h 50m

$167

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 2/19

7:10 am-10:43 am

Nonstop2h 33m

Boston Logan Intl

Tue 2/25

3:30 pm-5:32 pm

Nonstop3h 02m

$178

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/30

12:51 pm-6:26 pm

1 stop4h 35m

Boston Logan Intl

Mon 2/3

6:00 am-8:03 am

Nonstop3h 03m

$187

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 1/26

8:05 am-11:26 am

Nonstop2h 21m

Boston Logan Intl

Thu 1/30

6:00 am-8:08 am

Nonstop3h 08m

$212

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 2/13

4:14 pm-1:43 pm

1 stop20h 29m

Worcester

Mon 2/17

2:15 pm-10:45 am

1 stop21h 30m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

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 January 16, 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 January 16, 2025.

The most flights from CHI to USMA are scheduled on a Thursday (55 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (21 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 January 16, 2025.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Southwest, JetBlue and Spirit Airlines. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.1
Very good
4,659 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

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.

8.1
Very good
4,659 reviews
8.1
Very good
4,659 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

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.

8.0
Very good
8,511 reviews
8.1
Very good
4,659 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

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.

7.5
Good
3,752 reviews
8.1
Very good
4,659 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

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.

7.4
Good
3,199 reviews
8.1
Very good
4,659 reviews

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.2

Overall

8.1

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 Frontier, with whom users have recently found tickets for as low as $55. 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?

  • 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: Korean Air (92%), Etihad Airways (89%), Scandinavian Airlines( 85%).

  • 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 $113 on average our data indicates $719 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.

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 January 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$316FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$116FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$86Average$551FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$141Average$441FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$153Average$279FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$154Average$435FlexibilityNo cancel feeOn-time69%
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