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Cheap flights from Chicago (CHI) to Massachusetts from $36

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 7/9. 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 10 — Jun 171
From?
To?
Mon 6/10
Mon 6/17
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 5, 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.
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 6/4$120
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 6/4$124
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 6/4$133
Thu 6/209:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/249:19 pmBOS - ORD
2 stops27h 31mSpirit Airlines
Deal found 6/5$134
Fri 7/126:11 pmMDW - BOS
1 stop14h 17mFrontier
Wed 9/119:16 amBOS - MDW
1 stop13h 39mFrontier
Deal found 6/4$134
Sat 6/157:00 amORD - BOS
1 stop11h 59mSpirit Airlines
Mon 6/246:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$135
Thu 6/278:27 amORD - BOS
1 stop12h 27mSpirit Airlines
Mon 7/13:42 pmBOS - ORD
1 stop6h 05mSpirit Airlines
Deal found 6/4$136
Fri 7/269:33 pmORD - BOS
Nonstop2h 26mSpirit Airlines
Wed 7/312:54 pmBOS - ORD
1 stop7h 04mSpirit Airlines
Deal found 6/3$137
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 6/4$137

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 5, 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.
Wed 8/217:59 pmMDW - BOS
1 stop10h 26mFrontier
Tue 8/2712:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/5$103
Tue 8/207:59 pmMDW - BOS
1 stop10h 26mFrontier
Tue 8/2712:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 6/5$111
Tue 8/277:59 pmMDW - BOS
1 stop10h 26mFrontier
Sat 8/3110:10 amBOS - MDW
1 stop10h 03mFrontier
Deal found 6/4$116
Tue 8/207:59 pmMDW - BOS
1 stop10h 26mFrontier
Mon 8/2612:20 pmBOS - MDW
1 stop7h 53mFrontier
Deal found 6/4$119
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 6/4$120
Tue 9/109:15 amORD - BDL
1 stop4h 45mSpirit Airlines
Wed 9/113:52 pmBDL - ORD
1 stop5h 32mSpirit Airlines
Deal found 6/4$120
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 6/4$124
Tue 8/207:00 amORD - BDL
1 stop12h 35mMultiple Airlines
Wed 9/113:52 pmBDL - ORD
1 stop5h 32mMultiple Airlines
Deal found 6/4$129
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/197:49 amBOS - MDW
1 stop6h 43mFrontier
Deal found 6/4$133

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 5, 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.
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Thu 6/206:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$62
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$63
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Fri 6/216:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/3$64
Sat 6/158:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 6/256:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$68
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/196:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$69
Wed 6/128:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Sun 6/166:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$71
Sat 6/158:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Thu 6/206:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$72
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Thu 6/206:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/3$73
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 6/4$77

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 5, 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.
Tue 7/99:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 6/4$36
Fri 9/209:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 6/4$37
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 6/4$41
Mon 7/299:33 pmORD - BOS
Nonstop2h 26mSpirit Airlines
Deal found 6/4$42
Mon 6/249:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 6/4$43
Mon 6/249:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 6/5$44
Tue 7/99:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 6/4$46
Tue 8/135:01 amORD - BOS
1 stop5h 45mFrontier
Deal found 6/5$47
Sun 9/229:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 6/4$49

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 5, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$101 - $237

Route

Depart

Return

Price

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Wed 8/21

1 stop10h 26m

Boston Logan Intl

Tue 8/27

1 stop7h 37m

$101

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Tue 8/20

1 stop10h 26m

Boston Logan Intl

Tue 8/27

1 stop7h 37m

$111

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/18

1 stop5h 49m

Boston Logan Intl

Mon 6/24

Nonstop2h 54m

$129

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/11

Nonstop2h 28m

Boston Logan Intl

Thu 6/13

Nonstop2h 54m

$130

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 8/22

Nonstop2h 26m

Boston Logan Intl

Mon 8/26

Nonstop2h 54m

$151

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 8/14

Nonstop2h 26m

Boston Logan Intl

Fri 8/23

Nonstop3h 00m

$157

Chicago O'Hare IntlHyannis Barnstable

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 7/31

1 stop4h 23m

Hyannis Barnstable

Wed 8/7

1 stop6h 06m

$202

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Mon 6/24

2 stops11h 25m

Boston Logan Intl

Wed 6/26

Nonstop2h 35m

$230

Chicago O'Hare IntlAlbany Intl

ORD - ALB

ORDALB

Chicago O'Hare Intl

Thu 8/15

Nonstop2h 05m

Albany Intl

Sat 8/24

Nonstop2h 25m

$237

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 5, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about JetBlue, Delta and Southwest. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
5,922 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

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
5,922 reviews
Southwest
8.2
Very good
5,922 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

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
5,922 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

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
5,922 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

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
5,922 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

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
385 reviews
Southwest
8.2
Very good
5,922 reviews

Comfort

8.1

Overall

8.2

Food

7.3

Boarding

8.3

Entertainment

7.8

Crew

8.7

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 $200 on Cheapflights?

    Yes, there are multiple flights from Chicago to Massachusetts for under $200. The cheapest flight booked recently is on Frontier for just $101, but on average you can expect to pay $130.

  • Are there nonstop flights from Chicago to Massachusetts for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Massachusetts under $200. A good price for a nonstop flight from Chicago to Massachusetts is less than $144.

  • 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, Wednesday, Thursday, Friday, Saturday.

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

    47 flight departures from Chicago to Massachusetts per day on average.
    Morning (6am - Noon) - 40% of flight departures
    Afternoon (Noon - 6pm) - 26% of flight departures
    Evening (6pm - Midnight) - 34% 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 2h 28m. Fly via Frontier or Spirit Airlines to get the fastest option. The distance between Chicago and Massachusetts is about 869 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Massachusetts one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as $36. However, be on the lookout for offers from Frontier and Delta, 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 $46 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.

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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 5, 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%
Orlando to Newark Airport flights
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USA to Switzerland flights
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Chicago to Tokyo flights
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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 5, 2024.
6%of flight departuresEarly morningMidnight to 6 am
31%of flight departuresMorning6 am to noon
51%of flight departuresAfternoonNoon to 6 pm
12%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

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Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Massachusetts?

Cheapflights makes it easy to find Chicago to Massachusetts flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Massachusetts?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Massachusetts from Chicago.

Can Cheapflights find flights from Chicago to Massachusetts with no change fees?

Certainly. Search results for flights to Massachusetts from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Chicago to Massachusetts become cheaper?

Yes, Cheapflights offers price alerts on Chicago to Massachusetts flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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