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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 2/3. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — BOS
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
1 adult, Economy
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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 November 21, 2024.

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 November 21, 2024.

This eDestinos deal was found by Cheapflights users on 11/20. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/109:58 amORD - BOS
1 stop13h 40mSpirit Airlines
Wed 12/115:00 amBOS - ORD
1 stop12h 06mSpirit Airlines
Deal found 11/20$101
This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1112:57 pmMDW - BOS
1 stop10h 33mFrontier
Wed 12/185:45 amBOS - MDW
1 stop8h 39mFrontier
Deal found 11/20$103
This Frontier deal was found by Cheapflights users on 11/20. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/1310:59 amORD - BOS
1 stop12h 31mFrontier
Tue 12/175:45 amBOS - ORD
1 stop11h 48mFrontier
Deal found 11/20$117
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/57:45 pmORD - BOS
1 stop13h 06mMultiple Airlines
Mon 12/98:54 amBOS - ORD
1 stop7h 49mMultiple Airlines
Deal found 11/19$151
This JetBlue deal was found by Cheapflights users on 11/19. 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.
Tue 12/104:40 pmORD - BOS
Nonstop2h 22mJetBlue
Tue 12/171:59 pmBOS - ORD
Nonstop2h 54mJetBlue
Deal found 11/19$157
This Southwest deal was found by Cheapflights users on 11/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/138:30 pmMDW - BOS
Nonstop2h 10mSouthwest
Sun 12/156:40 amBOS - MDW
Nonstop2h 45mSouthwest
Deal found 11/20$158
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Thu 12/123:50 pmORD - BOS
Nonstop2h 21mUnited Airlines
Sun 12/155:45 amBOS - ORD
1 stop4h 49mUnited Airlines
Deal found 11/19$167
This Delta deal was found by Cheapflights users on 11/19. 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.
Sun 12/156:30 amORD - BOS
Nonstop2h 30mDelta
Wed 12/187:25 amBOS - ORD
Nonstop3h 03mDelta
Deal found 11/19$177
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Mon 12/166:07 pmORD - BDL
1 stop14h 45mFrontier
Wed 12/184:00 pmBDL - ORD
1 stop6h 45mFrontier
Deal found 11/20$188
This FlightHub deal was found by Cheapflights users on 11/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/38:27 pmORD - BDL
1 stop24h 35mMultiple Airlines
Thu 12/510:55 amBDL - ORD
1 stop23h 59mMultiple Airlines
Deal found 11/20$193
This American Airlines deal was found by Cheapflights users on 11/19. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/257:25 amORD - BOS
Nonstop2h 34mAmerican Airlines
Mon 12/305:15 amBOS - ORD
Nonstop3h 04mAmerican Airlines
Deal found 11/19$198
This CheapOair deal was found by Cheapflights users on 11/20. 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.
Mon 12/1611:33 amMDW - BDL
1 stop21h 19mFrontier
Wed 12/184:00 pmBDL - MDW
1 stop6h 17mFrontier
Deal found 11/20$208

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 2,629,791 searches. Data last updated November 21, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

9:58 am-12:38 am

1 stop13h 40m

Boston Logan Intl

Wed 12/11

5:00 am-4:06 pm

1 stop12h 06m

$101

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Wed 12/11

12:57 pm-12:30 am

1 stop10h 33m

Boston Logan Intl

Wed 12/18

5:45 am-1:24 pm

1 stop8h 39m

$103

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 1/9

5:02 pm-12:30 am

1 stop6h 28m

Boston Logan Intl

Tue 1/14

6:00 am-1:34 pm

1 stop8h 34m

$108

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 1/13

4:53 pm-12:30 am

1 stop6h 37m

Boston Logan Intl

Tue 1/14

11:31 am-8:13 pm

1 stop9h 42m

$120

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

9:20 am-12:45 pm

Nonstop2h 25m

Boston Logan Intl

Tue 12/10

6:28 pm-8:24 pm

Nonstop2h 56m

$157

ChicagoBoston

MDW - BOS

MDWBOS

Chicago Midway

Fri 12/13

8:30 pm-11:40 pm

Nonstop2h 10m

Boston Logan Intl

Sun 12/15

6:40 am-8:25 am

Nonstop2h 45m

$158

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 12/10

10:14 am-3:43 pm

1 stop4h 29m

Boston Logan Intl

Sun 1/12

6:10 am-8:14 am

Nonstop3h 04m

$166

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 12/15

6:30 am-10:00 am

Nonstop2h 30m

Boston Logan Intl

Wed 12/18

7:25 am-9:28 am

Nonstop3h 03m

$177

ChicagoBoston

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sun 1/5

8:30 pm-12:15 am

Nonstop2h 45m

Boston Logan Intl

Fri 1/10

6:00 am-8:08 am

Nonstop3h 08m

$182

ChicagoHartford

ORD - BDL

ORDBDL

Chicago O'Hare Intl

Fri 1/24

5:10 am-5:05 pm

1 stop10h 55m

Hartford Bradley Intl

Sun 1/26

7:40 pm-10:16 pm

1 stop27h 36m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

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 November 21, 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.

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 November 21, 2024.

The most flights from CHI to USMA are scheduled on a Monday (63 on average). You will have fewer flight options on Saturday, 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 November 21, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Spirit Airlines, Frontier and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,015 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,758 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Qatar Airways
7.5
Good
3,832 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,396 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,015 reviews

Boarding

8.2

Overall

8.1

Comfort

8.1

Food

7.2

Entertainment

7.7

Crew

8.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 Delta, 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 O'Hare Intl - Hartford Bradley Intl or Chicago Midway - Boston Logan 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 (96%), Avianca (95%), Royal Jordanian( 94%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $63. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $107 on average our data indicates $439 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 2,629,791 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$38Average$96FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$329FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$69Average$116FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$83Average$556FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$137Average$457FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$148Average$434FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$153Average$267FlexibilityNo cancel feeOn-time63%
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