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Cape Cod and the Islands

$96+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ACK
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$310
(American Airlines)

One-way from

$96
(JetBlue)

Popular in

April

Cheapest in

September

Average price

$227
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. 8% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 31, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
mié. 8/137:15 amORD - ACK
2 stops6h 31mDelta
mié. 8/203:26 pmACK - ORD
1 stop7h 27mDelta
Deal found 7/29$259
This American Airlines deal was found by Cheapflights users on 7/29. 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.
mié. 8/138:09 amORD - ACK
1 stop7h 27mAmerican Airlines
mié. 8/2012:24 pmACK - ORD
1 stop5h 47mAmerican Airlines
Deal found 7/29$278
This American Airlines deal was found by Cheapflights users on 7/29. 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.
sáb. 8/1611:12 amORD - HYA
Nonstop2h 39mAmerican Airlines
sáb. 8/233:25 pmHYA - ORD
Nonstop3h 06mAmerican Airlines
Deal found 7/29$310
This Expedia deal was found by Cheapflights users on 7/30. 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.
mar. 9/26:15 amORD - ACK
1 stop4h 38mJetBlue
vie. 9/54:10 pmACK - ORD
1 stop5h 39mJetBlue
Deal found 7/30$339
This Delta deal was found by Cheapflights users on 7/29. 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.
lun. 8/259:30 amMDW - ACK
2 stops29h 39mDelta
mié. 8/273:26 pmACK - MDW
2 stops18h 09mDelta
Deal found 7/29$368
This United Airlines deal was found by Cheapflights users on 7/30. 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.
sáb. 8/1610:35 amORD - ACK
Nonstop2h 54mUnited Airlines
mié. 8/206:46 pmACK - ORD
1 stop5h 39mUnited Airlines
Deal found 7/30$369
This American Airlines deal was found by Cheapflights users on 7/29. 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.
mar. 8/196:06 amORD - MVY
1 stop8h 31mAmerican Airlines
vie. 8/222:03 pmMVY - ORD
1 stop8h 08mAmerican Airlines
Deal found 7/29$388
This Delta deal was found by Cheapflights users on 7/30. 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.
mié. 8/277:00 amORD - MVY
1 stop5h 33mDelta
mié. 9/33:20 pmMVY - ORD
1 stop6h 27mDelta
Deal found 7/30$408
This Expedia deal was found by Cheapflights users on 7/31. 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.
jue. 9/46:59 pmORD - MVY
2 stops17h 21mJetBlue
lun. 9/810:17 amMVY - ORD
2 stops11h 32mJetBlue
Deal found 7/31$498
This United deal was found by Cheapflights users on 7/31. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 8/139:15 amORD - PVC
1 stop7h 24mMultiple Airlines
mié. 8/203:24 pmPVC - ORD
1 stop17h 41mMultiple Airlines
Deal found 7/31$593
This Mytrip deal was found by Cheapflights users on 7/30. 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.
jue. 8/1410:12 amORD - HYA
2 stops9h 15mMultiple Airlines
lun. 8/189:57 amHYA - ORD
2 stops13h 25mMultiple Airlines
Deal found 7/30$604
This JetBlue deal was found by Cheapflights users on 7/30. 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.
sáb. 10/119:42 amORD - PVC
1 stop4h 31mJetBlue
mié. 10/1510:35 amPVC - ORD
1 stop8h 20mJetBlue
Deal found 7/30$625

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 julio 31, 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

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

mié. 8/13

7:15 am-2:46 pm

2 stops6h 31m

Nantucket Memorial

mié. 8/20

3:26 pm-9:53 pm

1 stop7h 27m

$259

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

mié. 8/13

8:09 am-4:36 pm

1 stop7h 27m

Nantucket Memorial

mié. 8/20

12:24 pm-5:11 pm

1 stop5h 47m

$278

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

sáb. 8/16

11:12 am-2:51 pm

Nonstop2h 39m

Hyannis Barnstable

sáb. 8/23

3:25 pm-5:31 pm

Nonstop3h 06m

$310

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

mar. 9/2

6:15 am-11:53 am

1 stop4h 38m

Nantucket Memorial

vie. 9/5

4:10 pm-8:49 pm

1 stop5h 39m

$339

ChicagoNantucket

MDW - ACK

MDWACK

Chicago Midway

lun. 8/25

9:30 am-4:09 pm

2 stops29h 39m

Nantucket Memorial

mié. 8/27

3:26 pm-8:35 am

2 stops18h 09m

$368

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

sáb. 8/16

10:35 am-2:29 pm

Nonstop2h 54m

Nantucket Memorial

mié. 8/20

6:46 pm-11:25 pm

1 stop5h 39m

$369

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

mar. 8/19

6:06 am-3:37 pm

1 stop8h 31m

West Tisbury Martha's Vineyard

vie. 8/22

2:03 pm-9:11 pm

1 stop8h 08m

$388

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

mié. 8/27

7:00 am-1:33 pm

1 stop5h 33m

West Tisbury Martha's Vineyard

mié. 9/3

3:20 pm-8:47 pm

1 stop6h 27m

$408

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

jue. 9/4

6:59 pm-1:20 pm

2 stops17h 21m

West Tisbury Martha's Vineyard

lun. 9/8

10:17 am-8:49 pm

2 stops11h 32m

$498

ChicagoProvincetown

ORD - PVC

ORDPVC

Chicago O'Hare Intl

mié. 8/13

9:15 am-5:39 pm

1 stop7h 24m

Provincetown

mié. 8/20

3:24 pm-8:05 am

1 stop17h 41m

$593

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 29 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

What is the cheapest time of day to fly from CHI to KDT?

Find hourly flight availability from Chicago to Cape Cod and the Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated julio 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Cape Cod and the Islands as you normally would.

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 julio 31, 2025.
Read through reviews of airlines operating flights from Chicago to Cape Cod and the Islands, such as Delta, United 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
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
JetBlue
7.3
Good
2,914 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Overall

8.0

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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 $96. However, be on the lookout for offers from Delta and American 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.

  • What are the most reliable airlines from Chicago to Cape Cod and the Islands?

    The top 3 most reliable airlines when flying from Chicago to Cape Cod and the Islands are American Airlines (100%), Republic Airways (100%) and SkyWest Airlines (83%).

  • What are the cheapest flights from Chicago to Cape Cod and the Islands?

    Looking for the cheapest flight from Chicago to Cape Cod and the Islands? While on average our users pay $263, our data indicates the cheapest price to be $263. The most popular route (Chicago O'Hare Intl - Nantucket Memorial), is priced around $248.

  • 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.
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Midway to Boston flights
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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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$226Average$572FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$304Average$620FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$359Average$554FlexibilityNo cancel feeOn-time71%

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