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Cape Cod and the Islands

$79+ 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 8/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ACK
Aug 2 — Aug 91
Sun 8/2
Sun 8/9
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 July 3, 2026.

This JetBlue deal was found by Cheapflights users on 6/30. 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.
Mon 8/316:00 am
ORD
-
ACK
1 stop8h 24m
JetBlue
Wed 9/212:02 pm
ACK
-
ORD
1 stop6h 33m
JetBlue
Deal found 6/30$166
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Tue 8/256:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Sat 8/294:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Deal found 6/30$167
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Sat 8/299:40 am
ORD
-
MVY
1 stop5h 32m
JetBlue
Tue 9/15:05 pm
MVY
-
ORD
1 stop5h 53m
JetBlue
Deal found 6/30$174
This Priceline deal was found by Cheapflights users on 6/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/129:35 am
ORD
-
HYA
1 stop4h 38m
JetBlue
Sat 8/154:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Deal found 6/28$183
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/159:40 am
ORD
-
ACK
1 stop4h 44m
JetBlue
Wed 8/1912:02 pm
ACK
-
ORD
1 stop6h 33m
JetBlue
Deal found 7/1$190
This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/279:40 am
ORD
-
ACK
1 stop4h 44m
JetBlue
Mon 8/314:21 pm
ACK
-
ORD
1 stop6h 37m
JetBlue
Deal found 6/29$210
This Priceline deal was found by Cheapflights users on 6/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Wed 8/54:20 pm
HYA
-
ORD
1 stop6h 38m
JetBlue
Deal found 6/29$211
This SmartFares deal was found by Cheapflights users on 6/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/149:42 am
ORD
-
ACK
1 stop4h 42m
JetBlue
Fri 8/214:22 pm
ACK
-
ORD
1 stop6h 36m
JetBlue
Deal found 6/30$226
This JetBlue deal was found by Cheapflights users on 7/2. 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 8/156:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Sat 8/224:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Deal found 7/2$227
This Priceline deal was found by Cheapflights users on 7/1. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/276:00 am
ORD
-
ACK
1 stop8h 24m
JetBlue
Sun 8/303:33 pm
ACK
-
ORD
1 stop4h 54m
JetBlue
Deal found 7/1$228
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Sun 9/136:20 am
ORD
-
MVY
1 stop7h 45m
JetBlue
Thu 9/174:00 pm
MVY
-
ORD
1 stop7h 06m
JetBlue
Deal found 6/30$246
This JetBlue deal was found by Cheapflights users on 6/30. 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.
Wed 7/226:00 am
ORD
-
HYA
1 stop8h 13m
JetBlue
Sat 7/254:53 pm
HYA
-
ORD
1 stop6h 05m
JetBlue
Deal found 6/30$246

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 July 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$166
(JetBlue)

One-way from

$79
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$241
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. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 3, 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

Tue 8/25

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Sat 8/29

4:53 pm-9:58 pm

1 stop6h 05m

$167
Quickest round-trip

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 8/12

9:35 am-3:13 pm

1 stop4h 38m

Hyannis Barnstable

Sat 8/15

4:53 pm-9:58 pm

1 stop6h 05m

$183

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 8/29

9:40 am-4:12 pm

1 stop5h 32m

West Tisbury Martha's Vineyard

Tue 9/1

5:05 pm-9:58 pm

1 stop5h 53m

$190

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/15

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Sat 8/22

4:53 pm-9:58 pm

1 stop6h 05m

$211

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/22

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Mon 8/24

4:20 pm-9:58 pm

1 stop6h 38m

$262

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 7/22

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Sat 7/25

4:53 pm-9:58 pm

1 stop6h 05m

$262

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 7/25

6:00 am-3:19 pm

1 stop8h 19m

Nantucket Memorial

Tue 7/28

11:25 am-7:15 pm

1 stop8h 50m

$262

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 8/22

6:00 am-3:13 pm

1 stop8h 13m

Hyannis Barnstable

Mon 8/31

4:20 pm-9:58 pm

1 stop6h 38m

$290

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Fri 8/14

6:00 am-3:24 pm

1 stop8h 24m

Nantucket Memorial

Mon 8/17

3:33 pm-7:27 pm

1 stop4h 54m

$291

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Fri 7/17

9:42 am-4:10 pm

1 stop5h 28m

West Tisbury Martha's Vineyard

Tue 7/21

5:26 pm-9:58 pm

1 stop5h 32m

$316

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

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

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 July 3, 2026.

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 July 3, 2026.
Read through reviews of airlines operating flights from Chicago to Cape Cod and the Islands, such as American Airlines. 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.
American Airlines
7.1
Good
11,766 reviews

Boarding

7.5

Overall

7.1

Entertainment

6.8

Crew

7.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.
American Airlines
7.1
Good
11,766 reviews
American Airlines
7.1
Good
11,766 reviews

Boarding

7.5

Overall

7.1

Entertainment

6.8

Crew

7.9

Comfort

7.2

Food

6.4

Reviews

1 / 20
4.0
Okay

Elizabeth,Mar 2026

ORD - MIA

Staff was rude and flight attendants 2 out of 3 looked like they had just been thru a hurricane.

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 8h 11m. JetBlue provides one of the quickest options available for as low as $359. 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 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 $509, our data indicates the cheapest price to be $258. The most popular route (Chicago O'Hare Intl - Nantucket Memorial), is priced around $218.

  • 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

Browse thousands of different options on Cheapflights for your next trip

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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 July 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$162Average$393FlexibilityNo cancel feeOn-time62%
DeltaCheapest$207Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$319Average$546FlexibilityNo cancel feeOn-time71%

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