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Cheap flights from Chicago (CHI) to Massachusetts from $59

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 5/11. 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 6 — May 131
From?
To?
Mon 5/6
Mon 5/13
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 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 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 2,899,487 searches. Data last updated May 1, 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.
Tue 6/117:33 amORD - BOS
1 stop10h 49mSpirit Airlines
Sun 6/166:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 4/30$158
Wed 5/810:58 amORD - BOS
2 stops21h 52mSpirit Airlines
Thu 5/2310:27 pmBOS - ORD
1 stop13h 41mSpirit Airlines
Deal found 5/1$161
Tue 5/145:36 pmORD - BOS
3 stops27h 00mSpirit Airlines
Thu 5/1610:27 pmBOS - ORD
1 stop13h 41mSpirit Airlines
Deal found 4/30$162
Thu 6/139:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/178:00 pmBOS - ORD
2 stops25h 47mSpirit Airlines
Deal found 4/30$163
Wed 5/87:00 amORD - BOS
3 stops15h 26mSpirit Airlines
Tue 5/147:36 pmBOS - ORD
3 stops21h 59mSpirit Airlines
Deal found 5/1$165
Sat 5/117:30 amORD - BOS
1 stop13h 06mSpirit Airlines
Wed 5/159:20 amBOS - ORD
2 stops15h 09mSpirit Airlines
Deal found 5/1$167
Wed 5/87:00 amORD - BOS
1 stop7h 13mSpirit Airlines
Wed 5/153:35 pmBOS - ORD
1 stop6h 00mSpirit Airlines
Deal found 5/1$168
Mon 5/209:25 pmORD - BOS
1 stop16h 19mSpirit Airlines
Sun 5/261:53 pmBOS - ORD
1 stop6h 52mSpirit Airlines
Deal found 5/1$169
Sat 5/257:30 amORD - BOS
2 stops16h 27mSpirit Airlines
Thu 6/612:07 pmBOS - ORD
1 stop9h 34mSpirit Airlines
Deal found 4/30$170

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 2,899,487 searches. Data last updated May 1, 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.
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/189:49 amBOS - MDW
1 stop22h 05mFrontier
Deal found 4/30$101
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 5/1$102
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/189:49 amBOS - MDW
1 stop11h 24mFrontier
Deal found 5/1$103
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/1811:29 amBOS - MDW
2 stops20h 25mFrontier
Deal found 4/30$106
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/1811:29 amBOS - MDW
2 stops9h 44mFrontier
Deal found 5/1$108
Fri 5/103:44 pmMDW - BOS
1 stop15h 24mFrontier
Sat 5/189:49 amBOS - MDW
1 stop11h 24mFrontier
Deal found 5/1$121
Thu 5/95:56 pmMDW - BOS
1 stop13h 12mFrontier
Sat 5/189:49 amBOS - MDW
1 stop11h 24mFrontier
Deal found 4/30$122
Fri 5/103:44 pmMDW - BOS
1 stop15h 24mFrontier
Sat 5/1811:29 amBOS - MDW
2 stops9h 44mFrontier
Deal found 4/30$127
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 5/1$128

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 2,899,487 searches. Prices were last updated on May 1, 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.
Tue 5/2110:58 amORD - BOS
2 stops11h 28mSpirit Airlines
Thu 5/305:15 pmBOS - ORD
2 stops24h 20mSpirit Airlines
Deal found 5/1$159
Tue 5/281:30 pmORD - BOS
1 stop19h 54mFrontier
Fri 5/3110:04 amBOS - ORD
1 stop16h 04mFrontier
Deal found 4/30$160
Thu 5/307:49 amMDW - BOS
1 stop24h 15mFrontier
Thu 6/612:37 pmBOS - MDW
1 stop7h 56mFrontier
Deal found 4/30$160
Wed 5/810:58 amORD - BOS
2 stops21h 52mSpirit Airlines
Thu 5/2310:27 pmBOS - ORD
1 stop13h 41mSpirit Airlines
Deal found 5/1$161
Fri 5/171:15 pmMDW - BOS
2 stops20h 24mFrontier
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Deal found 5/1$161
Tue 5/145:36 pmORD - BOS
3 stops27h 00mSpirit Airlines
Thu 5/1610:27 pmBOS - ORD
1 stop13h 41mSpirit Airlines
Deal found 4/30$162
Sun 5/197:49 amMDW - BOS
1 stop24h 15mFrontier
Mon 5/2011:14 amBOS - MDW
1 stop11h 50mFrontier
Deal found 4/30$162
Fri 5/317:15 pmORD - BOS
Nonstop2h 26mJetBlue
Tue 6/44:25 pmBOS - ORD
Nonstop2h 55mJetBlue
Deal found 5/1$163
Tue 5/215:33 amORD - BOS
1 stop5h 24mMultiple Airlines
Fri 5/249:44 pmBOS - ORD
1 stop27h 48mMultiple Airlines
Deal found 5/1$164

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 2,899,487 searches. Data last updated May 1, 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.
Tue 6/117:33 amORD - BOS
1 stop10h 49mSpirit Airlines
Sun 6/166:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 4/30$158
Sat 6/15:01 amORD - BOS
1 stop6h 08mMultiple Airlines
Fri 6/1412:07 pmBOS - ORD
1 stop7h 58mMultiple Airlines
Deal found 4/30$159
Thu 6/136:35 pmORD - BOS
1 stop15h 14mMultiple Airlines
Mon 6/176:30 amBOS - ORD
Nonstop2h 54mMultiple Airlines
Deal found 5/1$160
Thu 5/307:49 amMDW - BOS
1 stop24h 15mFrontier
Thu 6/612:37 pmBOS - MDW
1 stop7h 56mFrontier
Deal found 4/30$160
Wed 5/810:58 amORD - BOS
2 stops21h 52mSpirit Airlines
Thu 5/2310:27 pmBOS - ORD
1 stop13h 41mSpirit Airlines
Deal found 5/1$161
Fri 5/171:15 pmMDW - BOS
2 stops20h 24mFrontier
Wed 5/228:19 amBOS - MDW
1 stop6h 50mFrontier
Deal found 5/1$161
Tue 5/145:36 pmORD - BOS
3 stops27h 00mSpirit Airlines
Thu 5/1610:27 pmBOS - ORD
1 stop13h 41mSpirit Airlines
Deal found 4/30$162
Sun 5/197:49 amMDW - BOS
1 stop24h 15mFrontier
Mon 5/2011:14 amBOS - MDW
1 stop11h 50mFrontier
Deal found 4/30$162
Thu 6/139:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/178:00 pmBOS - ORD
2 stops25h 47mSpirit Airlines
Deal found 4/30$163

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 2,899,487 searches. Data last updated May 1, 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.
Tue 7/29:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 7/96:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 4/29$158
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Fri 6/216:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/1$159
Thu 7/49:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 7/96:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 4/29$160
Tue 7/169:04 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Wed 7/246:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 4/30$161
Sat 6/17:15 pmORD - BOS
Nonstop2h 26mJetBlue
Wed 6/126:10 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 4/30$162
Fri 5/317:15 pmORD - BOS
Nonstop2h 26mJetBlue
Tue 6/44:25 pmBOS - ORD
Nonstop2h 55mJetBlue
Deal found 5/1$163
Tue 7/29:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 7/166:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 4/30$164
Sat 7/209:04 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Sat 8/36:35 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/1$165
Thu 6/69:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Sun 6/96:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 4/30$166

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 2,899,487 searches. Data last updated May 1, 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.
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/189:49 amBOS - MDW
1 stop22h 05mFrontier
Deal found 4/30$101
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Wed 5/1512:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 5/1$102
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/189:49 amBOS - MDW
1 stop11h 24mFrontier
Deal found 5/1$103
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/1811:29 amBOS - MDW
2 stops20h 25mFrontier
Deal found 4/30$106
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 5/1811:29 amBOS - MDW
2 stops9h 44mFrontier
Deal found 5/1$108
Fri 5/103:44 pmMDW - BOS
1 stop15h 24mFrontier
Sat 5/189:49 amBOS - MDW
1 stop11h 24mFrontier
Deal found 5/1$121
Thu 5/95:56 pmMDW - BOS
1 stop13h 12mFrontier
Sat 5/189:49 amBOS - MDW
1 stop11h 24mFrontier
Deal found 4/30$122
Fri 5/103:44 pmMDW - BOS
1 stop15h 24mFrontier
Sat 5/1811:29 amBOS - MDW
2 stops9h 44mFrontier
Deal found 4/30$127
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 5/1$128

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 2,899,487 searches. Data last updated May 1, 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.
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/30$59
Sat 5/118:17 pmMDW - BOS
1 stop10h 51mFrontier
Deal found 4/30$60
Sat 5/189:08 pmMDW - BOS
1 stop11h 35mFrontier
Deal found 4/30$61
Tue 6/1110:16 pmMDW - BOS
1 stop7h 43mFrontier
Deal found 4/30$64
Tue 6/1110:16 pmMDW - BOS
1 stop7h 43mFrontier
Deal found 5/1$68
Tue 8/277:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 4/30$69
Tue 6/1810:16 pmMDW - BOS
1 stop7h 43mFrontier
Deal found 4/30$76
Thu 5/95:56 pmMDW - BOS
1 stop13h 12mFrontier
Deal found 4/30$79
Tue 6/1810:16 pmMDW - BOS
1 stop7h 42mFrontier
Deal found 5/1$81

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 2,899,487 searches. Data last updated May 1, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$158 - $245

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/11

1 stop10h 49m

Boston Logan Intl

Sun 6/16

Nonstop2h 54m

$158

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 6/1

1 stop6h 08m

Boston Logan Intl

Fri 6/14

1 stop7h 58m

$159

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/30

1 stop24h 15m

Boston Logan Intl

Thu 6/6

1 stop7h 56m

$160

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 5/14

Nonstop2h 26m

Boston Logan Intl

Wed 5/22

Nonstop2h 54m

$167

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 6/1

Nonstop2h 29m

Boston Logan Intl

Sat 6/15

Nonstop2h 58m

$182

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/15

1 stop4h 00m

Boston Logan Intl

Wed 5/29

Nonstop2h 56m

$192

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/25

Nonstop2h 34m

Boston Logan Intl

Tue 5/28

1 stop4h 50m

$203

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Mon 7/8

1 stop25h 56m

Boston Logan Intl

Sat 7/13

1 stop15h 24m

$240

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Mon 5/13

Nonstop2h 15m

Boston Logan Intl

Wed 5/15

Nonstop2h 40m

$245

Flights are sorted by cheapest first

Deals found on 4/30

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 1, 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
6,129 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Food

7.3

Entertainment

7.8

Boarding

8.3

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

Southwest
8.2
Very good
6,129 reviews
Southwest
8.2
Very good
6,129 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Food

7.3

Entertainment

7.8

Boarding

8.3

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

Alaska Airlines
8.1
Very good
9,115 reviews
Southwest
8.2
Very good
6,129 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Food

7.3

Entertainment

7.8

Boarding

8.3

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

Delta
8.1
Very good
10,874 reviews
Southwest
8.2
Very good
6,129 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Food

7.3

Entertainment

7.8

Boarding

8.3

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

JetBlue
7.6
Good
4,561 reviews
Southwest
8.2
Very good
6,129 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Food

7.3

Entertainment

7.8

Boarding

8.3

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

Porter Airlines
7.4
Good
435 reviews
Southwest
8.2
Very good
6,129 reviews
Check prices

Overall

8.2

Comfort

8.1

Crew

8.7

Food

7.3

Entertainment

7.8

Boarding

8.3

Reviews

1 / 10

I was very relaxed and calm so I took a brief nap. The flight was pretty smooth.

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 Spirit Airlines for just $158, but on average you can expect to pay $163.

  • 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 $167.

  • 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: Sunday, Monday, Wednesday, Thursday, Friday, Saturday.

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

    62 flight departures from Chicago to Massachusetts per day on average.
    Early Morning (Midnight to 6am) - 3% of flight departures
    Morning (6am - Noon) - 47% of flight departures
    Afternoon (Noon - 6pm) - 34% of flight departures
    Evening (6pm - Midnight) - 16% 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 26m. Fly via Spirit Airlines, Frontier, or JetBlue 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 Frontier, with whom users have recently found tickets for as low as $59. However, be on the lookout for offers from JetBlue and Spirit Airlines, 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 - Worcester 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 $83. While the most popular route (Chicago O'Hare Intl - Boston Logan Intl) can be booked for $62 on average our data indicates $445 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), 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 5/1.

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 2,899,487 searches. Data last updated May 1, 2024.
AirlineCheapestAverageFlexibilityOn-time
Alaska AirlinesCheapest$69Average$148FlexibilityNo cancel feeOn-time75%
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JetBlueCheapest$69Average$306FlexibilityNo cancel feeOn-time62%
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United AirlinesCheapest$84Average$411FlexibilityNo cancel feeOn-time69%
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DeltaCheapest$89Average$429FlexibilityNo cancel feeOn-timeN/A
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Spirit AirlinesCheapest$104Average$192FlexibilityNo cancel feeOn-time65%
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American AirlinesCheapest$114Average$452FlexibilityNo 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 1, 2024.
5%of flight departuresEarly morningMidnight to 6 am
33%of flight departuresMorning6 am to noon
53%of flight departuresAfternoonNoon to 6 pm
9%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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