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Cheap flights from Chicago (CHI) to Massachusetts from $40

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 9/10. 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
May 18 — May 251
From?
To?
Sat 5/18
Sat 5/25
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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 46% 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 $269 on average during January, but can be found for as low as $99.

When is the cheapest time to fly from Chicago to Massachusetts (CHI - 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 Spirit Airlines flights from Chicago to Massachusetts

Explore cheap flight options specifically provided by Spirit Airlines for the route between Chicago and Massachusetts. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
Find some of the cheapest Spirit Airlines flights traveling from Chicago to Massachusetts. It's recommended that users confirm their flight details before booking.
Wed 9/119:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 9/187:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/12$63
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 6/1112:07 pmBOS - ORD
1 stop12h 38mSpirit Airlines
Deal found 5/12$64
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$73
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$74
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/123:42 pmBOS - ORD
1 stop6h 05mSpirit Airlines
Deal found 5/12$75
Fri 6/79:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/1112:07 pmBOS - ORD
1 stop12h 38mSpirit Airlines
Deal found 5/12$76
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$77
Wed 6/511:01 amORD - BOS
1 stop10h 59mSpirit Airlines
Sat 6/86:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$79
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Fri 6/76:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$80

Cheap Frontier flights from Chicago to Massachusetts

Explore cheap flight options specifically provided by Frontier for the route between Chicago and Massachusetts. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
To aid your search, here are some of the cheapest Frontier flights we've found from Chicago to Massachusetts. If these deals don't fit your criteria, make sure to check back soon as new deals are always added.
Wed 5/295:01 amORD - BOS
1 stop5h 07mFrontier
Sat 6/111:42 amBOS - ORD
1 stop14h 16mFrontier
Deal found 5/11$100
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Sat 6/112:59 pmBOS - MDW
1 stop7h 58mFrontier
Deal found 5/12$104
Tue 5/211:30 pmORD - BOS
1 stop19h 54mFrontier
Sat 6/111:42 amBOS - ORD
1 stop14h 16mFrontier
Deal found 5/12$110
Thu 6/68:51 pmMDW - BOS
1 stop10h 25mFrontier
Tue 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 5/12$121
Mon 6/310:02 pmMDW - BOS
1 stop8h 27mFrontier
Wed 6/59:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 5/12$124
Tue 8/207:59 pmMDW - BOS
1 stop10h 26mFrontier
Sat 8/2410:10 amBOS - MDW
1 stop10h 03mFrontier
Deal found 5/12$125
Sun 5/265:45 amORD - BOS
1 stop4h 57mFrontier
Wed 5/299:52 amBOS - ORD
1 stop16h 16mFrontier
Deal found 5/12$127
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Tue 6/1812:42 pmBOS - MDW
1 stop9h 38mFrontier
Deal found 5/12$128
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Mon 6/39:56 amBOS - MDW
1 stop11h 05mFrontier
Deal found 5/12$129

Cheap Chicago to Massachusetts flights in May & June 2024

Find cheap flight options from Chicago to Massachusetts specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,633,403 searches. Prices were last updated on May 13, 2024.
The lowest fares we've come across on flights traveling from Chicago to Massachusetts in May and June 2024. Check back soon for alternative fares.
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$73
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$74
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/123:42 pmBOS - ORD
1 stop6h 05mSpirit Airlines
Deal found 5/12$75
Fri 6/79:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/1112:07 pmBOS - ORD
1 stop12h 38mSpirit Airlines
Deal found 5/12$76
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$77
Wed 6/511:01 amORD - BOS
1 stop10h 59mSpirit Airlines
Sat 6/86:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$79
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Fri 6/76:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$80
Tue 6/49:35 amORD - BOS
1 stop11h 01mSpirit Airlines
Sat 6/86:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$81
Tue 6/49:35 amORD - BOS
1 stop11h 01mSpirit Airlines
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/13$82

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 2,633,403 searches. Data last updated May 13, 2024.
The lowest fares we've come across on flights traveling from Chicago to Massachusetts in May and June 2024. Check back soon for alternative fares.
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Sat 6/19:47 amBOS - MDW
1 stop11h 10mFrontier
Deal found 5/13$101
Thu 5/307:49 amMDW - BOS
1 stop24h 15mFrontier
Wed 6/59:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 5/13$115
Fri 5/3112:04 pmMDW - BOS
1 stop21h 40mFrontier
Wed 6/59:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 5/13$116
Thu 6/68:51 pmMDW - BOS
1 stop10h 25mFrontier
Tue 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 5/13$120
Thu 6/68:51 pmMDW - BOS
1 stop10h 25mFrontier
Tue 6/1112:36 pmBOS - MDW
1 stop9h 44mFrontier
Deal found 5/12$121
Mon 6/310:02 pmMDW - BOS
1 stop8h 27mFrontier
Wed 6/59:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 5/12$124
Tue 8/207:59 pmMDW - BOS
1 stop10h 26mFrontier
Sat 8/2410:10 amBOS - MDW
1 stop10h 03mFrontier
Deal found 5/12$125
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Tue 6/1812:42 pmBOS - MDW
1 stop9h 38mFrontier
Deal found 5/12$128
Wed 5/297:49 amMDW - BOS
1 stop23h 51mFrontier
Mon 6/39:56 amBOS - MDW
1 stop11h 05mFrontier
Deal found 5/12$129

Non-stop flights to Massachusetts from Chicago

Discover non-stop flight options from Chicago to Massachusetts. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 2,633,403 searches. Data last updated May 13, 2024.
If you're seeking options on non-stop flights from Chicago to Massachusetts, check out these fares. If you're looking for other options for flights from Chicago to Massachusetts, make sure to update the search form at the top of page.
Thu 7/259:30 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 7/306:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$161
Tue 6/189:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Fri 6/216:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/11$162
Thu 5/308:10 pmORD - BOS
Nonstop2h 36mDelta
Mon 6/36:25 amBOS - ORD
Nonstop2h 55mDelta
Deal found 5/12$163
Fri 7/269:30 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Sat 8/36:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$166
Thu 5/308:40 amORD - BOS
Nonstop2h 29mJetBlue
Sun 6/26:10 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 5/13$167
Sat 7/68:39 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Tue 7/96:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/11$168
Mon 7/89:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Fri 7/126:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$170
Tue 6/116:30 amORD - BOS
Nonstop2h 28mDelta
Tue 6/183:55 pmBOS - ORD
Nonstop2h 51mDelta
Deal found 5/13$172
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Fri 6/216:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/12$173

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 2,633,403 searches. Data last updated May 13, 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.
Tue 5/219:35 amORD - BOS
1 stop11h 01mSpirit Airlines
Sun 5/266:10 amBOS - ORD
1 stop11h 25mSpirit Airlines
Deal found 5/11$86
Tue 5/211:30 pmORD - BOS
1 stop19h 54mMultiple Airlines
Wed 5/2911:16 amBOS - ORD
1 stop10h 08mMultiple Airlines
Deal found 5/12$95
Tue 5/215:00 amORD - BOS
3 stops32h 22mSpirit Airlines
Wed 5/2911:16 amBOS - ORD
1 stop10h 08mSpirit Airlines
Deal found 5/12$107
Tue 5/211:30 pmORD - BOS
1 stop19h 54mMultiple Airlines
Thu 5/306:10 amBOS - ORD
1 stop11h 25mMultiple Airlines
Deal found 5/12$108
Tue 5/211:30 pmORD - BOS
1 stop19h 54mFrontier
Sat 6/111:42 amBOS - ORD
1 stop14h 16mFrontier
Deal found 5/12$110
Tue 5/219:15 pmORD - BOS
2 stops25h 11mSpirit Airlines
Sun 5/266:10 amBOS - ORD
1 stop12h 30mSpirit Airlines
Deal found 5/11$112
Tue 5/211:30 pmORD - BOS
1 stop19h 54mMultiple Airlines
Sun 5/266:10 amBOS - ORD
1 stop12h 30mMultiple Airlines
Deal found 5/12$113
Wed 5/225:01 amORD - BOS
1 stop5h 07mMultiple Airlines
Tue 5/2811:16 amBOS - ORD
1 stop10h 08mMultiple Airlines
Deal found 5/12$114
Tue 5/215:00 amORD - BOS
2 stops17h 26mSpirit Airlines
Tue 5/2811:16 amBOS - ORD
1 stop10h 08mSpirit Airlines
Deal found 5/12$117

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 2,633,403 searches. Data last updated May 13, 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 9/109:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 5/12$40
Mon 6/109:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 5/12$42
Fri 6/79:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 5/12$43
Fri 9/69:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 5/12$44
Wed 6/511:01 amORD - BOS
1 stop10h 59mSpirit Airlines
Deal found 5/13$45
Thu 9/129:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 5/12$47
Wed 5/295:01 amORD - BOS
1 stop5h 07mFrontier
Deal found 5/12$50
Wed 6/127:33 amORD - BOS
1 stop12h 02mSpirit Airlines
Deal found 5/12$51
Wed 7/107:02 amORD - BOS
1 stop11h 23mSpirit Airlines
Deal found 5/12$52

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 2,633,403 searches. Data last updated May 13, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$63 - $172

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/11

Nonstop2h 18m

Boston Logan Intl

Wed 9/18

Nonstop2h 33m

$63

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/5

Nonstop2h 29m

Boston Logan Intl

Tue 6/11

1 stop12h 38m

$64

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/5

Nonstop2h 29m

Boston Logan Intl

Wed 6/12

Nonstop2h 54m

$73

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/5

Nonstop2h 29m

Boston Logan Intl

Wed 6/12

Nonstop2h 54m

$74

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 6/1

1 stop6h 08m

Boston Logan Intl

Thu 6/6

Nonstop2h 54m

$99

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/29

1 stop5h 07m

Boston Logan Intl

Sat 6/1

1 stop14h 16m

$100

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/31

Nonstop2h 26m

Boston Logan Intl

Tue 6/4

Nonstop2h 54m

$137

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/30

Nonstop2h 36m

Boston Logan Intl

Mon 6/3

Nonstop2h 55m

$163

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 5/30

Nonstop2h 35m

Boston Logan Intl

Sun 6/2

1 stop4h 58m

$172

Flights are sorted by cheapest first

Deals found on 5/12

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

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 May 13, 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
8.2
Very good
6,054 reviews
Check prices

Crew

8.7

Comfort

8.1

Entertainment

7.8

Food

7.3

Boarding

8.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Southwest
8.2
Very good
6,054 reviews
Southwest
8.2
Very good
6,054 reviews
Check prices

Crew

8.7

Comfort

8.1

Entertainment

7.8

Food

7.3

Boarding

8.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Delta
8.0
Very good
10,736 reviews
Southwest
8.2
Very good
6,054 reviews
Check prices

Crew

8.7

Comfort

8.1

Entertainment

7.8

Food

7.3

Boarding

8.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

JetBlue
7.6
Good
4,497 reviews
Southwest
8.2
Very good
6,054 reviews
Check prices

Crew

8.7

Comfort

8.1

Entertainment

7.8

Food

7.3

Boarding

8.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

WestJet
7.6
Good
2,926 reviews
Southwest
8.2
Very good
6,054 reviews
Check prices

Crew

8.7

Comfort

8.1

Entertainment

7.8

Food

7.3

Boarding

8.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

Porter Airlines
7.4
Good
419 reviews
Southwest
8.2
Very good
6,054 reviews
Check prices

Crew

8.7

Comfort

8.1

Entertainment

7.8

Food

7.3

Boarding

8.3

Overall

8.2

Reviews

1 / 10

My original flight was delayed so they found this flight for me so I could arrive at a reasonable time

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 $63, but on average you can expect to pay $81.

  • 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 $176.

  • 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: Monday, Tuesday, Wednesday, Friday, Saturday.

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

    18 flight departures from Chicago to Massachusetts per day on average.
    Morning (6am - Noon) - 22% of flight departures
    Afternoon (Noon - 6pm) - 22% of flight departures
    Evening (6pm - Midnight) - 56% 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 18m. Fly via Spirit Airlines or Frontier 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 $40. However, be on the lookout for offers from Frontier 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 - Albany Intl as they are the most popular.

  • 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 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 (90%), Republic Airways (90%), EL AL( 90%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $89. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $62 on average our data indicates $915 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), Worcester Airport (ORH), West Tisbury Martha's Vineyard Airport (MVY), Hyannis Barnstable Airport (HYA), Provincetown Airport (PVC) 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 5/13.

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 2,633,403 searches. Data last updated May 13, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$63Average$416FlexibilityNo cancel feeOn-timeN/A
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Alaska AirlinesCheapest$69Average$148FlexibilityNo cancel feeOn-time75%
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JetBlueCheapest$73Average$314FlexibilityNo cancel feeOn-time62%
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Spirit AirlinesCheapest$73Average$173FlexibilityNo cancel feeOn-time65%
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United AirlinesCheapest$84Average$412FlexibilityNo cancel feeOn-time69%
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FrontierCheapest$84Average$168FlexibilityNo cancel feeOn-time62%
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American AirlinesCheapest$117Average$460FlexibilityNo 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.
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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 May 13, 2024.
3%of flight departuresEarly morningMidnight to 6 am
40%of flight departuresMorning6 am to noon
40%of flight departuresAfternoonNoon to 6 pm
17%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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