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Cheap flights from Chicago (CHI) to Massachusetts from $37

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 6/12. 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
Apr 24 — May 11
From?
To?
Wed 4/24
Wed 5/1
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 33 days early can save you up to 34% on average compared to booking a flight this week. If booking 33 days before your flight isn’t an option for you, users have found flights from Chicago to Massachusetts for as little as $228 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 $316 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, February can be a great choice for travel to Massachusetts. Flights to Massachusetts from Chicago in February are about $250 on average during February, but can be found for as low as $76.

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 American Airlines flights from Chicago to Massachusetts

Explore cheap flight options specifically provided by American 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 3,192,047 searches. Data last updated April 19, 2024.
Find some of the cheapest American Airlines flights traveling from Chicago to Massachusetts. It's recommended that users confirm their flight details before booking.
Sat 5/113:20 pmORD - BOS
1 stop4h 40mAmerican Airlines
Tue 5/148:50 amBOS - ORD
Nonstop2h 57mAmerican Airlines
Deal found 4/18$166
Fri 5/104:53 pmORD - BOS
1 stop5h 37mAmerican Airlines
Wed 5/155:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/17$167
Wed 5/19:55 amORD - BOS
1 stop5h 16mAmerican Airlines
Wed 5/155:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/18$176
Fri 5/104:53 pmORD - BOS
1 stop4h 15mAmerican Airlines
Wed 5/155:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/18$187
Thu 5/21:20 pmORD - BOS
1 stop5h 27mAmerican Airlines
Mon 5/65:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/18$192
Wed 5/16:25 pmORD - BOS
1 stop5h 27mAmerican Airlines
Mon 5/65:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 4/18$202
Wed 5/223:27 pmORD - BOS
Nonstop2h 17mAmerican Airlines
Sun 5/268:50 amBOS - ORD
Nonstop2h 57mAmerican Airlines
Deal found 4/18$203
Tue 4/303:34 pmORD - BOS
Nonstop2h 17mAmerican Airlines
Thu 5/27:30 amBOS - ORD
1 stop4h 55mAmerican Airlines
Deal found 4/18$208
Tue 4/301:20 pmORD - BOS
1 stop5h 27mAmerican Airlines
Fri 5/36:10 pmBOS - ORD
1 stop5h 14mAmerican Airlines
Deal found 4/17$216

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 3,192,047 searches. Data last updated April 19, 2024.
To aid your search, here are some of the cheapest Spirit Airlines 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 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/117:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$73
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/117:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$74
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 6/127:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$82
Sat 6/89:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 6/127:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$86
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Thu 6/137:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$92
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/1112:07 pmBOS - ORD
1 stop12h 37mSpirit Airlines
Deal found 4/18$93
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/1112:07 pmBOS - ORD
1 stop7h 58mSpirit Airlines
Deal found 4/18$94
Sat 6/89:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Thu 6/137:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$98
Wed 6/129:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Mon 6/177:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$104

Cheap Chicago to Massachusetts flights in April & May 2024

Find cheap flight options from Chicago to Massachusetts specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,192,047 searches. Prices were last updated on April 19, 2024.
The lowest fares we've come across on flights traveling from Chicago to Massachusetts in April and May 2024. Check back soon for alternative fares.
Sat 5/48:17 pmMDW - BOS
1 stop10h 51mFrontier
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/17$85
Sat 5/48:17 pmMDW - BOS
1 stop10h 51mFrontier
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/18$86
Thu 5/25:56 pmMDW - BOS
1 stop13h 12mFrontier
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/17$90
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Deal found 4/17$91
Thu 5/25:56 pmMDW - BOS
1 stop13h 12mFrontier
Wed 5/88:21 amBOS - MDW
1 stop14h 22mFrontier
Deal found 4/18$92
Thu 5/167:49 amMDW - BOS
1 stop24h 15mFrontier
Sat 5/189:49 amBOS - MDW
1 stop22h 05mFrontier
Deal found 4/18$93
Wed 5/158:25 amORD - BOS
1 stop24h 01mFrontier
Mon 5/2010:04 amBOS - ORD
1 stop16h 04mFrontier
Deal found 4/18$96
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/189:49 amBOS - MDW
1 stop22h 05mFrontier
Deal found 4/17$96
Thu 5/165:56 pmORD - BOS
1 stop14h 08mFrontier
Mon 5/2010:04 amBOS - ORD
1 stop16h 04mFrontier
Deal found 4/18$97

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 3,192,047 searches. Data last updated April 19, 2024.
The lowest fares we've come across on flights traveling from Chicago to Massachusetts in April and May 2024. Check back soon for alternative fares.
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/117:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$73
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/117:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$74
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 6/127:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$82
Sat 5/48:17 pmMDW - BOS
1 stop10h 51mFrontier
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/17$85
Sat 6/89:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 6/127:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$86
Sat 5/48:17 pmMDW - BOS
1 stop10h 51mFrontier
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/18$86
Thu 5/25:56 pmMDW - BOS
1 stop13h 12mFrontier
Wed 5/812:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 4/17$90
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Wed 5/2211:14 amBOS - MDW
1 stop11h 39mFrontier
Deal found 4/17$91
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Thu 6/137:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$92

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 3,192,047 searches. Data last updated April 19, 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.
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/117:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$73
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/117:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$74
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 6/127:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$82
Sat 6/89:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 6/127:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$86
Wed 6/59:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Thu 6/137:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$92
Thu 6/69:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 6/117:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$94
Sat 6/89:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Thu 6/137:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$98
Wed 6/129:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Mon 6/177:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$104
Tue 6/119:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Mon 6/177:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 4/18$106

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 3,192,047 searches. Data last updated April 19, 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.
Thu 5/25:51 pmORD - BOS
1 stop13h 17mFrontier
Mon 5/138:21 amBOS - ORD
1 stop27h 26mFrontier
Deal found 4/18$132
Thu 5/25:51 pmORD - BOS
1 stop13h 17mFrontier
Sat 5/49:08 amBOS - ORD
1 stop15h 35mFrontier
Deal found 4/18$134
Fri 5/38:25 amORD - BOS
1 stop22h 43mFrontier
Mon 5/138:21 amBOS - ORD
1 stop27h 26mFrontier
Deal found 4/18$136
Fri 5/38:25 amORD - BOS
1 stop22h 43mFrontier
Mon 5/138:21 amBOS - ORD
1 stop27h 26mFrontier
Deal found 4/18$137
Thu 5/25:51 pmORD - BOS
1 stop13h 17mFrontier
Sun 5/59:08 amBOS - ORD
1 stop16h 51mFrontier
Deal found 4/18$143
Thu 5/25:51 pmORD - BOS
1 stop13h 17mFrontier
Sun 5/59:08 amBOS - ORD
1 stop16h 51mFrontier
Deal found 4/18$144
Wed 5/18:25 amORD - BOS
1 stop22h 43mFrontier
Mon 5/138:21 amBOS - ORD
1 stop27h 26mFrontier
Deal found 4/18$146
Mon 4/298:25 amORD - BOS
1 stop22h 43mFrontier
Sat 5/49:08 amBOS - ORD
1 stop15h 35mFrontier
Deal found 4/17$147
Wed 5/18:25 amORD - BOS
1 stop22h 43mFrontier
Wed 5/158:21 amBOS - ORD
1 stop14h 36mFrontier
Deal found 4/18$148

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 3,192,047 searches. Data last updated April 19, 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 6/129:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 4/17$37
Tue 6/119:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 4/17$46
Thu 6/69:20 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Deal found 4/18$49
Sat 5/48:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/18$49
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/18$54
Thu 5/25:56 pmMDW - BOS
1 stop13h 12mFrontier
Deal found 4/18$55
Sat 5/1810:55 amORD - BOS
1 stop8h 59mSpirit Airlines
Deal found 4/17$57
Sat 5/1110:55 amORD - BOS
1 stop8h 59mSpirit Airlines
Deal found 4/16$58
Sat 5/48:25 amORD - BOS
1 stop22h 43mFrontier
Deal found 4/18$59

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 3,192,047 searches. Data last updated April 19, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$73 - $166

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/5

Nonstop2h 18m

Boston Logan Intl

Tue 6/11

Nonstop2h 33m

$73

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 6/5

Nonstop2h 18m

Boston Logan Intl

Tue 6/11

Nonstop2h 33m

$74

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Sat 5/4

1 stop10h 51m

Boston Logan Intl

Wed 5/8

1 stop11h 44m

$86

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Sat 5/4

1 stop10h 51m

Boston Logan Intl

Sat 5/11

1 stop11h 00m

$89

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/11

1 stop8h 59m

Boston Logan Intl

Mon 5/13

1 stop27h 26m

$118

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/11

Nonstop2h 26m

Boston Logan Intl

Tue 5/14

Nonstop2h 54m

$137

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/11

1 stop5h 41m

Boston Logan Intl

Tue 5/14

Nonstop2h 53m

$151

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 5/10

Nonstop2h 36m

Boston Logan Intl

Tue 5/14

Nonstop3h 02m

$153

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/11

1 stop4h 40m

Boston Logan Intl

Tue 5/14

Nonstop2h 57m

$166

Flights are sorted by cheapest first

Deals found on 4/18

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 April 19, 2024.
To help decide which airline to fly from Chicago to Massachusetts, see what other customers have to say about American Airlines, Spirit Airlines and Frontier. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
6,208 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.4

Comfort

8.1

Entertainment

7.9

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.2
Very good
6,208 reviews
Southwest
8.2
Very good
6,208 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.4

Comfort

8.1

Entertainment

7.9

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.1
Very good
11,102 reviews
Southwest
8.2
Very good
6,208 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.4

Comfort

8.1

Entertainment

7.9

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.7
Good
4,669 reviews
Southwest
8.2
Very good
6,208 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.4

Comfort

8.1

Entertainment

7.9

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
11,333 reviews
Southwest
8.2
Very good
6,208 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.4

Comfort

8.1

Entertainment

7.9

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Porter Airlines
7.3
Good
439 reviews
Southwest
8.2
Very good
6,208 reviews
Check prices

Overall

8.2

Boarding

8.3

Crew

8.7

Food

7.4

Comfort

8.1

Entertainment

7.9

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

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 $73, but on average you can expect to pay $91.

  • 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 $104.

  • Are there last-minute flights available from Chicago to Massachusetts for under $200?

    There are currently 20+ open flights from Chicago to Massachusetts within the next 7 days for less than $200.

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

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

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

    16 flight departures from Chicago to Massachusetts per day on average.
    Morning (6am - Noon) - 63% of flight departures
    Afternoon (Noon - 6pm) - 13% of flight departures
    Evening (6pm - Midnight) - 25% 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 $37. 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 - Nantucket Memorial 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 (96%), Icelandair (90%), Etihad Airways( 90%).

  • What are the cheapest flights from Chicago to Massachusetts?

    Looking at all options, your cheapest flight can be booked for $84. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $73 on average our data indicates $477 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. Worcester Airport (ORH), Nantucket Memorial Airport (ACK), West Tisbury Martha's Vineyard Airport (MVY), Provincetown Airport (PVC), Hyannis Barnstable Airport (HYA) 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 4/18.

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 6 airlines flying from Chicago to Massachusetts

Discover the top 6 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 3,192,047 searches. Data last updated April 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$69Average$216FlexibilityNo cancel feeOn-time75%
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JetBlueCheapest$73Average$331FlexibilityNo cancel feeOn-time62%
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United AirlinesCheapest$84Average$425FlexibilityNo cancel feeOn-time69%
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DeltaCheapest$89Average$428FlexibilityNo cancel feeOn-timeN/A
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American AirlinesCheapest$114Average$473FlexibilityNo cancel feeOn-time71%
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Spirit AirlinesCheapest$130Average$196FlexibilityNo cancel feeOn-time65%
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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 April 19, 2024.
3%of flight departuresEarly morningMidnight to 6 am
31%of flight departuresMorning6 am to noon
56%of flight departuresAfternoonNoon to 6 pm
10%of flight departuresEvening6 pm to midnight
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6 AM
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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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