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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 7/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MVY
Feb 17 — Feb 241
Tue 2/17
Tue 2/24
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 January 18, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$237
(Delta)

One-way from

$113
(Delta)

Popular in

April

Cheapest in

January

Average price

$207
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. 6% potential increase in price ($16 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 January 2026
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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 January 18, 2026.

This Delta deal was found by Cheapflights users on 1/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/138:55 am
ORD
-
ACK
2 stops8h 10m
Delta
Tue 6/1610:00 am
ACK
-
ORD
2 stops9h 41m
Delta
Deal found 1/17$237
This Delta deal was found by Cheapflights users on 1/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:30 am
ORD
-
ACK
1 stop4h 57m
Delta
Wed 7/291:45 pm
ACK
-
ORD
1 stop6h 37m
Delta
Deal found 1/16$250
This American Airlines deal was found by Cheapflights users on 1/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2110:42 am
ORD
-
ACK
1 stop4h 46m
American Airlines
Wed 7/292:19 pm
ACK
-
ORD
1 stop7h 31m
American Airlines
Deal found 1/17$257
This American Airlines deal was found by Cheapflights users on 1/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1510:50 am
ORD
-
HYA
Nonstop2h 35m
American Airlines
Sat 8/293:00 pm
HYA
-
ORD
Nonstop2h 52m
American Airlines
Deal found 1/17$288
This American Airlines deal was found by Cheapflights users on 1/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/201:55 pm
ORD
-
ACK
Nonstop2h 40m
American Airlines
Sat 6/279:45 am
ACK
-
ORD
Nonstop2h 58m
American Airlines
Deal found 1/16$354
This American Airlines deal was found by Cheapflights users on 1/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:42 am
ORD
-
HYA
1 stop5h 45m
American Airlines
Sat 7/113:00 pm
HYA
-
ORD
Nonstop2h 52m
American Airlines
Deal found 1/16$376
This American Airlines deal was found by Cheapflights users on 1/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/910:05 am
ORD
-
ACK
1 stop6h 04m
American Airlines
Sun 8/235:14 pm
ACK
-
ORD
1 stop7h 11m
American Airlines
Deal found 1/16$413
This United Airlines deal was found by Cheapflights users on 1/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1310:35 am
ORD
-
ACK
Nonstop2h 54m
United Airlines
Tue 6/164:15 pm
ACK
-
ORD
1 stop6h 13m
United Airlines
Deal found 1/17$458
This American Airlines deal was found by Cheapflights users on 1/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:00 am
ORD
-
HYA
1 stop6h 08m
American Airlines
Sun 8/301:02 pm
HYA
-
ORD
1 stop7h 24m
American Airlines
Deal found 1/17$464
This United Airlines deal was found by Cheapflights users on 1/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/910:35 am
ORD
-
ACK
Nonstop2h 54m
United Airlines
Sun 8/234:32 pm
ACK
-
ORD
Nonstop3h 15m
United Airlines
Deal found 1/16$481
This Expedia deal was found by Cheapflights users on 1/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/207:40 am
ORD
-
HYA
1 stop8h 40m
Multiple Airlines
Sat 1/247:05 am
HYA
-
ORD
1 stop11h 38m
Multiple Airlines
Deal found 1/16$495
This Expedia deal was found by Cheapflights users on 1/17. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/217:40 am
ORD
-
HYA
1 stop8h 40m
Multiple Airlines
Fri 1/237:05 am
HYA
-
ORD
1 stop11h 38m
Multiple Airlines
Deal found 1/17$515

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 January 18, 2026.
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

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 6/13

8:55 am-6:05 pm

2 stops8h 10m

Nantucket Memorial

Tue 6/16

10:00 am-6:41 pm

2 stops9h 41m

$237

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 6/20

1:55 pm-5:35 pm

Nonstop2h 40m

Nantucket Memorial

Sat 6/27

9:45 am-11:43 am

Nonstop2h 58m

$354

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 7/4

10:42 am-5:27 pm

1 stop5h 45m

Hyannis Barnstable

Sat 7/11

3:00 pm-4:52 pm

Nonstop2h 52m

$376

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 6/13

10:35 am-2:29 pm

Nonstop2h 54m

Nantucket Memorial

Tue 6/16

4:15 pm-9:28 pm

1 stop6h 13m

$458

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Tue 7/7

5:56 pm-10:11 am

1 stop15h 15m

West Tisbury Martha's Vineyard

Sun 7/12

7:35 pm-10:14 am

1 stop15h 39m

$518

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 1/31

7:40 am-7:50 pm

1 stop11h 10m

Nantucket Memorial

Wed 2/4

1:30 pm-5:43 pm

1 stop5h 13m

$544

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 6/20

7:10 am-6:05 pm

2 stops9h 55m

Nantucket Memorial

Sat 6/27

1:45 pm-8:24 pm

2 stops7h 39m

$557

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 6/13

8:55 am-4:17 pm

2 stops6h 22m

West Tisbury Martha's Vineyard

Tue 6/16

4:59 pm-10:43 pm

1 stop6h 44m

$564

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 2/2

8:55 am-3:35 pm

1 stop5h 40m

West Tisbury Martha's Vineyard

Fri 2/6

1:28 pm-5:43 pm

1 stop5h 15m

$573

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 1/31

7:40 am-3:35 pm

1 stop6h 55m

West Tisbury Martha's Vineyard

Wed 2/4

10:10 am-5:43 pm

1 stop8h 33m

$573

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/16

Showing 1-10 of 37 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 January 18, 2026.
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
8,075 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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
8,075 reviews
Delta
7.9
Good
8,075 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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
11,157 reviews
Delta
7.9
Good
8,075 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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
2,891 reviews
Delta
7.9
Good
8,075 reviews

Food

7.2

Boarding

8.1

Overall

7.9

Comfort

7.9

Entertainment

7.8

Crew

8.5

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 2h 40m. Delta provides one of the quickest options available for as low as $354. The distance from Chicago to Cape Cod and the Islands is about 921 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Chicago to Cape Cod and the Islands one-way?

    The cheapest airline one-way is JetBlue, with whom users have recently found tickets for as low as $113. However, be on the lookout for offers from American Airlines and United Airlines, as they are both options that can get you from Chicago to Cape Cod and the Islands for a low price.

  • 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 - Nantucket Memorial. You may also consider Chicago O'Hare Intl - West Tisbury Martha's Vineyard or Chicago O'Hare Intl - Hyannis Barnstable.

  • 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.

See more FAQs

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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.
O'Hare Intl to Boston flights
Midway to Boston flights
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O'Hare Intl to New Bedford flights

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 January 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$123Average$461FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$304Average$620FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$319Average$553FlexibilityNo cancel feeOn-time71%

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