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Cheap flights from Chicago (CHI) to Massachusetts from $56

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 8/28. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — BOS
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
1 adult, Economy
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How far in advance should I book a flight from Chicago to Massachusetts?

Users have found that booking a flight from Chicago to Massachusetts at least 51 days early can save you up to 42% on average compared to booking a flight this week. If booking 51 days before your flight isn’t an option for you, users have found flights from Chicago to Massachusetts for as little as $263 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $346 for flights departing within the next 3 days.

What is the cheapest month to fly from Chicago to Massachusetts?

Due to multiple factors, expect to potentially pay more when booking in June. For low rates, January can be a great choice for travel to Massachusetts. Flights to Massachusetts from Chicago in January are about $267 on average during January, but can be found for as low as $99.

What is the cheapest time of day to fly from CHI to MA?

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.

Cheap Chicago to Massachusetts flights in June & July 2024

Find cheap flight options from Chicago to Massachusetts specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Massachusetts in June and July 2024. Check back soon for alternative fares.
Sat 6/158:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$71
Sat 7/139:33 pmORD - BOS
Nonstop2h 26mSpirit Airlines
Wed 7/246:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$72
Thu 6/209:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/246:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$73
Sat 6/228:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 6/256:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/6$74
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/176:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$75
Tue 6/189:19 amORD - BOS
1 stop11h 43mSpirit Airlines
Wed 6/196:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$76
Tue 6/189:19 amORD - BOS
1 stop11h 43mSpirit Airlines
Fri 6/2111:28 amBOS - ORD
1 stop7h 44mSpirit Airlines
Deal found 6/5$77
Fri 6/287:18 amORD - BOS
1 stop10h 36mSpirit Airlines
Tue 7/26:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/6$78
Mon 7/19:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 7/26:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$79

Chicago to Massachusetts 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Massachusetts in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Massachusetts in June and July 2024. Check back soon for alternative fares.
Sat 6/158:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$71
Sat 7/139:33 pmORD - BOS
Nonstop2h 26mSpirit Airlines
Wed 7/246:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$72
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/246:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$73
Wed 7/1010:14 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Wed 7/176:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$74
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/176:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$75
Tue 6/189:19 amORD - BOS
1 stop11h 43mSpirit Airlines
Wed 6/196:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$76
Tue 6/189:19 amORD - BOS
1 stop11h 43mSpirit Airlines
Fri 6/2111:28 amBOS - ORD
1 stop7h 44mSpirit Airlines
Deal found 6/5$77
Mon 7/19:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 7/26:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$79
Wed 7/1710:14 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 7/226:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$80

Chicago to Massachusetts flights leaving soon

Find last-minute flight options from Chicago to Massachusetts for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
Have a look at some of the flights available from Chicago to Massachusetts departing last-minute. Tip: verify your flight details before completing your reservation.
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$62
Sat 6/158:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$71
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/256:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/6$73
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/176:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$75
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Sat 6/226:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$79
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Sun 6/166:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$81
Thu 6/139:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/6$82
Thu 6/139:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$83
Sat 6/158:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Sat 6/226:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/5$84

One-way flights to Massachusetts from Chicago

Search for one-way flight options from Chicago to Massachusetts. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
Users traveling one-way from Chicago to Massachusetts can select one of these great deals. Users in need of a round-trip flight from Chicago to Massachusetts instead should update the search form at the top of page.
Wed 8/287:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$56
Wed 8/147:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$59
Sat 8/317:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$61
Tue 8/137:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$63
Tue 8/277:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 6/5$64
Fri 9/67:59 pmMDW - BOS
1 stop9h 56mFrontier
Deal found 6/5$67
Wed 7/177:26 amORD - BDL
1 stop6h 46mSpirit Airlines
Deal found 6/6$70
Thu 6/205:01 amORD - BOS
1 stop5h 29mFrontier
Deal found 6/5$77
Wed 8/76:38 pmORD - BOS
1 stop4h 39mJetBlue
Deal found 6/5$78

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 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$64 - $163

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/11

1 stop12h 46m

Boston Logan Intl

Sun 9/15

Nonstop2h 52m

$64

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/20

Nonstop2h 28m

Boston Logan Intl

Mon 6/24

Nonstop2h 54m

$65

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 7/18

Nonstop2h 26m

Boston Logan Intl

Wed 7/24

Nonstop2h 54m

$68

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 6/27

Nonstop2h 28m

Boston Logan Intl

Tue 7/2

Nonstop2h 54m

$69

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 7/10

Nonstop2h 28m

Boston Logan Intl

Mon 7/15

Nonstop2h 54m

$70

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 8/8

Nonstop2h 26m

Boston Logan Intl

Mon 8/12

1 stop5h 49m

$90

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Wed 8/21

1 stop10h 26m

Boston Logan Intl

Tue 8/27

1 stop7h 37m

$98

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 8/17

Nonstop2h 28m

Boston Logan Intl

Wed 8/21

Nonstop2h 59m

$137

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 6/17

Nonstop2h 26m

Boston Logan Intl

Tue 6/18

Nonstop2h 57m

$163

Flights are sorted by cheapest first

Deals found on 6/5

No data available for this route at this time. Please check back soon.

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.

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 June 6, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about Spirit Airlines, Delta and JetBlue. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Crew

8.7

Comfort

8.1

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,918 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Crew

8.7

Comfort

8.1

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Delta
8.0
Very good
10,368 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Crew

8.7

Comfort

8.1

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

JetBlue
7.6
Good
4,316 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Crew

8.7

Comfort

8.1

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

WestJet
7.5
Good
2,856 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Crew

8.7

Comfort

8.1

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Porter Airlines
7.4
Good
382 reviews
Southwest
8.2
Very good
5,918 reviews

Entertainment

7.8

Overall

8.2

Crew

8.7

Comfort

8.1

Boarding

8.3

Food

7.3

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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.

  • Can I find flights from Chicago to Massachusetts for under $100 on Cheapflights?

    Yes, there are multiple flights from Chicago to Massachusetts for under $100. The cheapest flight booked recently is on Spirit Airlines for just $64, but on average you can expect to pay $76.

  • Are there nonstop flights from Chicago to Massachusetts for under $100 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Massachusetts under $100. A good price for a nonstop flight from Chicago to Massachusetts is less than $66.

  • Are there last-minute flights available from Chicago to Massachusetts for under $100?

    There are currently 20+ open flights from Chicago to Massachusetts within the next 7 days for less than $100.

  • What days are nonstop flights available from Chicago to Massachusetts?

    Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Thursday, Friday, Saturday.

  • How many flights depart from Chicago to Massachusetts on average per day?

    42 flight departures from Chicago to Massachusetts per day on average.
    Morning (6am - Noon) - 36% of flight departures
    Afternoon (Noon - 6pm) - 21% of flight departures
    Evening (6pm - Midnight) - 43% of flight departures

  • How long is the flight from Chicago to Massachusetts?

    There are many flights that can get you from Chicago to Massachusetts in 12h 46m. Fly via Spirit Airlines to get the fastest option. The distance between Chicago and Massachusetts is about 869 mi.

  • 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 $56. 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?

    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: Etihad Airways (91%), Icelandair (89%), TAP AIR PORTUGAL( 89%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $68. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $48 on average our data indicates $421 when flying from Chicago to Massachusetts.

  • What does ORD to BOS mean?

    ORD stands for Chicago O'Hare Intl Airport, while BOS stands for Boston Logan Intl Airport. These codes are often called IATA codes, a set of identifiers established by IATA (International Air Transport Association) that is widely used by airlines and the aviation industry. Nantucket Memorial Airport (ACK), West Tisbury Martha's Vineyard Airport (MVY), Worcester Airport (ORH), Hyannis Barnstable Airport (HYA), Boston Harbor SPB Airport (BNH) are some additional IATA codes for airports related to your trip.

  • Can I find deals for flights from Chicago to Massachusetts that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Massachusetts flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Massachusetts with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Massachusetts flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Massachusetts that allow pets onboard?

    Many airlines flying from Chicago to Massachusetts offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Massachusetts?

    Yes, you can often find last-minute deals on Chicago to Massachusetts flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Massachusetts flight deals updated?

    The Chicago to Massachusetts flight deals you see on this page were last updated on 6/5.

  • What are the most popular airlines that fly from Chicago to Massachusetts?

    Undisclosed Carrier, American Airlines and Alaska Airlines are the most popular airlines when flying 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 $328). 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

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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 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$47Average$140FlexibilityNo cancel feeOn-time65%
DeltaCheapest$63Average$384FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$68Average$414FlexibilityNo cancel feeOn-time62%
Alaska AirlinesCheapest$69Average$148FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$84Average$402FlexibilityNo cancel feeOn-time69%
FrontierCheapest$84Average$168FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$119Average$454FlexibilityNo cancel feeOn-time71%
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Search flights from Chicago to Massachusetts by cabin class

Find flights from Chicago to Massachusetts, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Hourly flight availability from Chicago to Massachusetts

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 June 6, 2024.
8%of flight departuresEarly morningMidnight to 6 am
31%of flight departuresMorning6 am to noon
47%of flight departuresAfternoonNoon to 6 pm
14%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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