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Cape Cod and the Islands

$209+ Cheap flights from O'Hare Intl (ORD) 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — ACK
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Cape Cod and the Islands

Keep the following information in mind while searching for O'Hare Intl to Cape Cod and the Islands flight deals. Data was last updated November 3, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$410
(JetBlue)

One-way from

$209
(Kiwi.com)

Popular in

April

Cheapest in

September

Average price

$230
Provider with most accurate pricing for Chicago (CHI)-Boston Logan Intl flight deals.
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From Chicago O'Hare Intl to Cape Cod and the Islands
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One-way flight from Chicago O'Hare Intl to Cape Cod and the Islands
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Highest demand for flights based on searches. 6% potential increase in price ($14 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 O'Hare Intl to Cape Cod and the Islands

Cheapest flights from O'Hare Intl to Cape Cod and the Islands
Explore the most affordable flight options available from O'Hare Intl to Cape Cod and the Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This JetBlue deal was found by Cheapflights users on 11/2. 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.
Wed 11/1211:20 amORD - HYA
1 stop6h 19mJetBlue
Thu 11/1312:07 pmHYA - ORD
1 stop6h 48mJetBlue
Deal found 11/2$575
This United deal was found by Cheapflights users on 11/2. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:21 pmORD - MVY
2 stops15h 10mMultiple Airlines
Sun 1/44:10 pmMVY - ORD
1 stop18h 39mMultiple Airlines
Deal found 11/2$669
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Fri 12/196:45 amORD - HYA
1 stop5h 25mJetBlue
Tue 12/3012:07 pmHYA - ORD
1 stop7h 39mJetBlue
Deal found 11/2$675
This JetBlue deal was found by Cheapflights users on 11/2. 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 12/206:45 amORD - HYA
1 stop5h 25mJetBlue
Sat 1/1012:07 pmHYA - ORD
1 stop6h 37mJetBlue
Deal found 11/2$680
This JetBlue deal was found by Cheapflights users on 11/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1711:20 amORD - HYA
1 stop6h 19mJetBlue
Mon 11/242:30 pmHYA - ORD
1 stop5h 57mJetBlue
Deal found 11/3$695
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/183:26 pmORD - ACK
2 stops18h 19mMultiple Airlines
Sat 11/225:25 pmACK - ORD
2 stops30h 48mMultiple Airlines
Deal found 11/3$740
This United deal was found by Cheapflights users on 11/2. 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 United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/69:25 pmORD - MVY
1 stop11h 24mMultiple Airlines
Sat 11/81:34 pmMVY - ORD
1 stop20h 56mMultiple Airlines
Deal found 11/2$782
This Expedia deal was found by Cheapflights users on 11/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1811:20 amORD - ACK
1 stop8h 20mJetBlue
Sat 11/2211:05 amACK - ORD
1 stop9h 45mJetBlue
Deal found 11/3$794
This JetBlue deal was found by Cheapflights users on 11/2. 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 12/206:45 amORD - MVY
1 stop5h 38mJetBlue
Sat 1/101:34 pmMVY - ORD
1 stop5h 10mJetBlue
Deal found 11/2$879
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2512:39 pmORD - MVY
2 stops31h 06mMultiple Airlines
Sat 1/39:52 amMVY - ORD
1 stop13h 15mMultiple Airlines
Deal found 11/2$917
This JetBlue deal was found by Cheapflights users on 11/2. 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.
Wed 11/126:45 amORD - MVY
1 stop5h 38mJetBlue
Thu 11/1310:09 amMVY - ORD
1 stop8h 46mJetBlue
Deal found 11/2$925
This Kiwi.com deal was found by Cheapflights users on 11/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/2212:39 pmORD - MVY
2 stops20h 10mMultiple Airlines
Thu 1/19:52 amMVY - ORD
1 stop13h 15mMultiple Airlines
Deal found 11/2$927

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 3, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Cape Cod and the Islands that are best for you.

Fly from

O'Hare Intl

Fly to

Cape Cod and the Islands

Route

Depart

Return

Price

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Wed 12/24

6:21 pm-10:31 am

2 stops15h 10m

West Tisbury Martha's Vineyard

Sun 1/4

4:10 pm-9:49 am

1 stop18h 39m

$669

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Fri 12/19

6:45 am-1:10 pm

1 stop5h 25m

Hyannis Barnstable

Tue 12/30

12:07 pm-6:46 pm

1 stop7h 39m

$675

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Sat 12/20

6:45 am-1:10 pm

1 stop5h 25m

Hyannis Barnstable

Sat 1/10

12:07 pm-5:44 pm

1 stop6h 37m

$680

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Mon 11/17

11:20 am-6:39 pm

1 stop6h 19m

Hyannis Barnstable

Mon 11/24

2:30 pm-7:27 pm

1 stop5h 57m

$695

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Tue 11/18

3:26 pm-10:45 am

2 stops18h 19m

Nantucket Memorial

Sat 11/22

5:25 pm-11:13 pm

2 stops30h 48m

$740

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Tue 11/18

11:20 am-8:40 pm

1 stop8h 20m

Nantucket Memorial

Sat 11/22

11:05 am-7:50 pm

1 stop9h 45m

$794

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Fri 4/10

11:30 am-6:39 pm

1 stop6h 09m

Hyannis Barnstable

Sun 4/12

12:07 pm-5:31 pm

1 stop6h 24m

$835

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 12/20

6:45 am-1:23 pm

1 stop5h 38m

West Tisbury Martha's Vineyard

Sat 1/10

1:34 pm-5:44 pm

1 stop5h 10m

$879

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Thu 12/25

12:39 pm-8:45 pm

2 stops31h 06m

West Tisbury Martha's Vineyard

Sat 1/3

9:52 am-10:07 pm

1 stop13h 15m

$917

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Thu 12/25

12:39 pm-8:45 pm

2 stops31h 06m

West Tisbury Martha's Vineyard

Thu 1/1

9:52 am-10:07 pm

1 stop13h 15m

$917

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 41 results
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Best time to book a flight from O'Hare Intl to Cape Cod and the Islands

Have a flexible travel schedule? Discover the best time to fly to Cape Cod and the Islands from O'Hare Intl 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 O'Hare Intl Airport 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 3, 2025.
See what other customers who have flown with United Airlines, American Airlines, and JetBlue from Chicago O'Hare Intl Airport to Cape Cod and the Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,996 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,996 reviews
United Airlines
7.4
Good
8,996 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,036 reviews
United Airlines
7.4
Good
8,996 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
JetBlue
7.2
Good
2,906 reviews
United Airlines
7.4
Good
8,996 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl 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 O'Hare Intl Airport to Cape Cod and the Islands?

    Airlines like JetBlue fly from Chicago O'Hare Intl Airport to Cape Cod and the Islands in about 5h 25m. The time it takes to get you to your destination can typically vary by up to . The distance between Chicago O'Hare Intl Airport and Cape Cod and the Islands is about 905 mi.

  • What are the most popular routes from Chicago O'Hare Intl Airport to Cape Cod and the Islands?

    While some choose either Chicago O'Hare Intl - Hyannis Barnstable or Chicago O'Hare Intl - West Tisbury Martha's Vineyard, Chicago O'Hare Intl - Nantucket Memorial is the most popular route from Chicago O'Hare Intl Airport to Cape Cod and the Islands.

  • Can I find deals for flights from O'Hare Intl to Cape Cod and the Islands that include hotel bookings?

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

  • How can I find direct flights from O'Hare Intl 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 O'Hare Intl to Cape Cod and the Islands.

  • Can I find deals for business class flights from O'Hare Intl to Cape Cod and the Islands?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 3 airlines flying from O'Hare Intl to Cape Cod and the Islands

Discover the top 3 airlines that operate flights from O'Hare Intl 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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$162Average$461FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$304Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$319Average$548FlexibilityNo cancel feeOn-time71%

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