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Cape Cod and the Islands

$113+ Cheap flights from Chicago (CHI) to Cape Cod and the Islands

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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ACK
Dec 26 — Jan 21
Fri 12/26
Fri 1/2
1 adult, Economy
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Cheap flight deals from Chicago to Cape Cod and the Islands

Keep the following information in mind while searching for Chicago to Cape Cod and the Islands flight deals. Data was last updated November 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$580
(JetBlue)

One-way from

$113
(Delta)

Popular in

April

Cheapest in

September

Average price

$257
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
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From Chicago (CHI) to Cape Cod and the Islands
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One-way flight from Chicago (CHI) to Cape Cod and the Islands
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Highest demand for flights based on searches. 5% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Find flight deals from Chicago to Cape Cod and the Islands

Cheapest flights from Chicago to Cape Cod and the Islands
Explore the most affordable flight options available from Chicago to Cape Cod and the Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 26, 2025.

This JetBlue deal was found by Cheapflights users on 11/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1011:25 amORD - HYA
1 stop4h 55mJetBlue
Sun 12/1412:07 pmHYA - ORD
1 stop8h 36mJetBlue
Deal found 11/25$625
This JetBlue deal was found by Cheapflights users on 11/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:00 amORD - MVY
1 stop5h 23mJetBlue
Sun 12/71:34 pmMVY - ORD
1 stop7h 09mJetBlue
Deal found 11/26$894
This Mytrip deal was found by Cheapflights users on 11/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/41:52 pmORD - ACK
3 stops26h 38mMultiple Airlines
Sun 12/75:15 pmACK - ORD
2 stops27h 46mMultiple Airlines
Deal found 11/24$1,160

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Cape Cod and the Islands 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 2,558,603 searches. Data last updated November 26, 2025.
Use the filters below to find and compare flights from Chicago to Cape Cod and the Islands that are best for you.

Fly from

Chicago

Fly to

Cape Cod and the Islands

Route

Depart

Return

Price

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 3/24

10:56 am-5:20 pm

1 stop5h 24m

Hyannis Barnstable

Sun 3/29

12:07 pm-5:24 pm

1 stop6h 17m

$580

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 12/10

11:25 am-5:20 pm

1 stop4h 55m

Hyannis Barnstable

Sun 12/14

12:07 pm-7:43 pm

1 stop8h 36m

$625

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Tue 3/24

10:56 am-6:50 pm

1 stop6h 54m

West Tisbury Martha's Vineyard

Sun 3/29

10:10 am-5:24 pm

1 stop8h 14m

$699

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Fri 5/22

7:30 am-2:19 pm

1 stop5h 49m

West Tisbury Martha's Vineyard

Sun 5/24

12:15 pm-7:22 pm

1 stop8h 07m

$793

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 12/6

7:00 am-1:23 pm

1 stop5h 23m

West Tisbury Martha's Vineyard

Sun 12/7

1:34 pm-7:43 pm

1 stop7h 09m

$894

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Thu 5/7

9:30 am-3:35 pm

1 stop5h 05m

West Tisbury Martha's Vineyard

Sun 5/10

1:28 pm-7:26 pm

1 stop6h 58m

$924

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Fri 5/22

9:30 am-7:50 pm

1 stop9h 20m

Nantucket Memorial

Mon 5/25

2:45 pm-7:26 pm

1 stop5h 41m

$989

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Fri 5/22

12:15 pm-6:05 pm

1 stop4h 50m

Nantucket Memorial

Mon 5/25

10:00 am-6:41 pm

2 stops9h 41m

$1,014

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sun 4/26

11:30 am-5:20 pm

1 stop4h 50m

Hyannis Barnstable

Wed 4/29

12:07 pm-7:26 pm

1 stop8h 19m

$1,018

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sun 4/26

11:30 am-5:20 pm

1 stop4h 50m

Hyannis Barnstable

Tue 4/28

12:07 pm-5:31 pm

1 stop6h 24m

$1,035

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/25

Showing 1-10 of 27 results
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Best time to book a flight from Chicago to Cape Cod and the Islands

Have a flexible travel schedule? Discover the best time to fly to Cape Cod and the Islands 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Cape Cod and the Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Cape Cod and the Islands

Get insights into the airlines that provide service to Cape Cod and the Islands. 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 Cape Cod and the Islands. Reviews last updated November 26, 2025.
Read through reviews of airlines operating flights from Chicago to Cape Cod and the Islands, such as Delta, American Airlines, and JetBlue. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,998 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,038 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
JetBlue
7.2
Good
2,905 reviews
Delta
7.9
Good
7,998 reviews

Crew

8.5

Overall

7.9

Boarding

8.1

Comfort

7.9

Food

7.3

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Cape Cod and the Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Chicago to Cape Cod and the Islands?

    A quick flight from Chicago to Cape Cod and the Islands can take about 5h 24m. JetBlue provides one of the quickest options available for as low as $580. The distance from Chicago to Cape Cod and the Islands is about 905 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the most popular routes from Chicago to Cape Cod and the Islands?

    The most popular route from Chicago to Cape Cod and the Islands is Chicago O'Hare Intl - West Tisbury Martha's Vineyard. You may also consider Chicago O'Hare Intl - Nantucket Memorial or Chicago Midway - Nantucket Memorial.

  • Can I find deals for flights from Chicago to Cape Cod and the Islands that include hotel bookings?

    Yes. In addition to deals on Chicago to Cape Cod and the Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Cape Cod and the Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Cape Cod and the Islands.

  • Can I find deals for business class flights from Chicago to Cape Cod and the Islands?

    Yes. Cheapflights offers flight deals from Chicago to Cape Cod and the Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

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Alternative routes for Chicago to Cape Cod and the Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Cape Cod and the Islands

Discover the top 3 airlines that operate flights from Chicago to Cape Cod and the Islands. 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 2,558,603 searches. Data last updated November 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$162Average$461FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$304Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$319Average$553FlexibilityNo cancel feeOn-time71%

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