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Cape Cod and the Islands

$134+ 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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ACK
Jun 6 — Jun 131
Sat 6/6
Sat 6/13
1 adult, Economy
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Cheap 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 May 7, 2026.

This American Airlines deal was found by Cheapflights users on 5/7. 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 7/46:35 am
ORD
-
HYA
1 stop4h 40m
American Airlines
Sat 7/116:08 pm
HYA
-
ORD
1 stop6h 22m
American Airlines
Deal found 5/7$265
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/205:59 am
ORD
-
ACK
1 stop7h 03m
American Airlines
Sat 6/275:09 pm
ACK
-
ORD
1 stop7h 21m
American Airlines
Deal found 5/6$282
This Delta deal was found by Cheapflights users on 5/5. 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 6/307:05 am
ORD
-
ACK
1 stop7h 43m
Delta
Fri 7/312:06 pm
ACK
-
ORD
1 stop5h 39m
Delta
Deal found 5/5$290
This Delta deal was found by Cheapflights users on 5/5. 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 5/266:00 am
ORD
-
ACK
1 stop4h 27m
Delta
Tue 6/24:00 pm
ACK
-
ORD
1 stop5h 46m
Delta
Deal found 5/5$298
This Delta deal was found by Cheapflights users on 5/3. 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 7/216:00 am
ORD
-
ACK
1 stop4h 32m
Delta
Wed 7/293:24 pm
ACK
-
ORD
1 stop7h 28m
Delta
Deal found 5/3$315
This Delta deal was found by Cheapflights users on 5/5. 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 6/305:30 am
ORD
-
ACK
2 stops9h 18m
Delta
Sat 7/412:06 pm
ACK
-
ORD
1 stop5h 44m
Delta
Deal found 5/5$321
This American Airlines deal was found by Cheapflights users on 5/5. 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 6/306:29 am
ORD
-
ACK
1 stop7h 34m
American Airlines
Sat 7/412:25 pm
ACK
-
ORD
Nonstop3h 14m
American Airlines
Deal found 5/5$326
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Fri 6/197:10 am
ORD
-
HYA
1 stop5h 25m
American Airlines
Fri 6/266:07 pm
HYA
-
ORD
1 stop6h 23m
American Airlines
Deal found 5/6$330
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Wed 7/16:29 am
ORD
-
ACK
1 stop7h 34m
American Airlines
Sat 7/42:31 pm
ACK
-
ORD
1 stop6h 12m
American Airlines
Deal found 5/5$336
This American Airlines deal was found by Cheapflights users on 5/5. 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.
Thu 7/308:29 pm
ORD
-
ACK
1 stop13h 20m
American Airlines
Tue 8/411:19 am
ACK
-
ORD
1 stop7h 10m
American Airlines
Deal found 5/5$337
This Delta deal was found by Cheapflights users on 5/4. 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 6/136:05 am
ORD
-
ACK
1 stop7h 34m
Delta
Sat 6/203:20 pm
ACK
-
ORD
1 stop7h 28m
Delta
Deal found 5/4$345
This American Airlines deal was found by Cheapflights users on 5/6. 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 8/225:00 am
ORD
-
MVY
1 stop6h 00m
American Airlines
Sat 8/2912:30 pm
MVY
-
ORD
1 stop5h 44m
American Airlines
Deal found 5/6$354

Find 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 May 7, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$282
(American Airlines)

One-way from

$134
(American Airlines)

Popular in

April

Cheapest in

January

Average price

$227
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Boston Logan Intl flights.
Search Deals
From Chicago (CHI) to Cape Cod and the Islands
Search Deals
One-way flight from Chicago (CHI) to Cape Cod and the Islands
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 7, 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

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 7/4

6:00 am-2:24 pm

1 stop7h 24m

Hyannis Barnstable

Sat 7/11

6:08 pm-11:30 pm

1 stop6h 22m

$282

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Tue 6/30

7:05 am-3:48 pm

1 stop7h 43m

Nantucket Memorial

Fri 7/3

12:06 pm-4:45 pm

1 stop5h 39m

$290

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Tue 7/21

6:00 am-11:32 am

1 stop4h 32m

Nantucket Memorial

Wed 7/29

12:13 pm-6:29 pm

2 stops7h 16m

$351

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/22

6:00 am-1:20 pm

1 stop6h 20m

West Tisbury Martha's Vineyard

Sat 8/29

1:52 pm-7:22 pm

1 stop6h 30m

$354

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 5/30

6:07 am-1:01 pm

1 stop5h 54m

West Tisbury Martha's Vineyard

Sat 6/6

1:41 pm-11:03 pm

2 stops10h 22m

$393

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sun 6/21

10:25 am-2:19 pm

Nonstop2h 54m

Nantucket Memorial

Sat 6/27

3:14 pm-10:06 pm

1 stop7h 52m

$415

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Fri 5/29

6:07 am-12:39 pm

1 stop5h 32m

West Tisbury Martha's Vineyard

Mon 6/1

1:19 pm-9:35 am

1 stop21h 16m

$423

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 5/30

6:24 am-3:22 pm

2 stops7h 58m

West Tisbury Martha's Vineyard

Tue 6/2

12:04 pm-4:34 pm

1 stop5h 30m

$426

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Mon 8/24

9:39 am-4:09 pm

1 stop5h 30m

West Tisbury Martha's Vineyard

Sat 8/29

5:05 pm-9:55 pm

1 stop5h 50m

$427

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 7/4

10:12 am-4:09 pm

1 stop4h 57m

West Tisbury Martha's Vineyard

Wed 7/8

5:05 pm-9:27 pm

1 stop5h 22m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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 May 7, 2026.
Read through reviews of airlines operating flights from Chicago to Cape Cod and the Islands, such as Delta,American Airlines, andJetBlue. 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
8,459 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
Delta
7.9
Good
8,459 reviews
Delta
7.9
Good
8,459 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
American Airlines
7.1
Good
11,670 reviews
Delta
7.9
Good
8,459 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.
JetBlue
7.1
Good
2,980 reviews
Delta
7.9
Good
8,459 reviews

Entertainment

7.8

Food

7.2

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Joel,May 2026

ATL - JAX

The flight was delivered 50 minutes and taxing took what felt like 20 minutes to takeoff.

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 54m. American Airlines provides one of the quickest options available for as low as $415. 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 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.

See more FAQs

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Top 2 airlines flying from Chicago to Cape Cod and the Islands

Discover the top 2 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 May 7, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$162Average$658FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$333Average$542FlexibilityNo cancel feeOn-time71%

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