HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cape Cod and the Islands

$122+ 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 6/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — MVY
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Cape Cod and the Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 March 17, 2026.

This American Airlines deal was found by Cheapflights users on 3/14. 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 8/186:55 am
ORD
-
HYA
1 stop5h 13m
American Airlines
Tue 8/251:38 pm
HYA
-
ORD
1 stop7h 55m
American Airlines
Deal found 3/14$255
This Delta deal was found by Cheapflights users on 3/12. 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 7/286:00 am
ORD
-
MVY
1 stop4h 20m
Delta
Tue 8/44:59 pm
MVY
-
ORD
1 stop6h 44m
Delta
Deal found 3/12$256
This Delta deal was found by Cheapflights users on 3/12. 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 6/26:00 am
ORD
-
MVY
1 stop4h 24m
Delta
Sat 6/61:41 pm
MVY
-
ORD
1 stop5h 08m
Delta
Deal found 3/12$264
This American Airlines deal was found by Cheapflights users on 3/13. 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 7/215:00 am
ORD
-
ACK
1 stop6h 26m
American Airlines
Wed 7/292:32 pm
ACK
-
ORD
1 stop7h 47m
American Airlines
Deal found 3/13$278
This American Airlines deal was found by Cheapflights users on 3/15. 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 7/227:00 am
ORD
-
HYA
1 stop4h 58m
American Airlines
Thu 7/301:28 pm
HYA
-
ORD
1 stop5h 40m
American Airlines
Deal found 3/15$280
This Delta deal was found by Cheapflights users on 3/12. 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 7/2912:01 pm
ACK
-
ORD
2 stops9h 23m
Delta
Deal found 3/12$284
This Delta deal was found by Cheapflights users on 3/12. 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 8/17:10 am
ORD
-
MVY
2 stops8h 07m
Delta
Thu 8/64:59 pm
MVY
-
ORD
1 stop6h 44m
Delta
Deal found 3/12$321
This Delta deal was found by Cheapflights users on 3/16. 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.
Sat 5/307:05 am
ORD
-
MVY
1 stop7h 17m
Delta
Mon 6/11:19 pm
MVY
-
ORD
1 stop5h 30m
Delta
Deal found 3/16$328
This American Airlines deal was found by Cheapflights users on 3/13. 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 7/46:00 am
ORD
-
HYA
1 stop7h 24m
American Airlines
Sat 7/113:54 pm
HYA
-
ORD
Nonstop3h 34m
American Airlines
Deal found 3/13$340
This American Airlines deal was found by Cheapflights users on 3/14. 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.
Mon 7/205:00 am
ORD
-
ACK
1 stop6h 26m
American Airlines
Mon 7/204:51 pm
ACK
-
ORD
1 stop7h 30m
American Airlines
Deal found 3/14$386
This American Airlines deal was found by Cheapflights users on 3/13. 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 7/246:00 am
ORD
-
ACK
1 stop7h 03m
American Airlines
Tue 7/282:32 pm
ACK
-
ORD
1 stop7h 47m
American Airlines
Deal found 3/13$388
This American Airlines deal was found by Cheapflights users on 3/12. 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 8/266:06 am
ORD
-
MVY
1 stop4h 23m
American Airlines
Sun 8/304:55 pm
MVY
-
ORD
1 stop7h 30m
American Airlines
Deal found 3/12$393

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 March 17, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$255
(American Airlines)

One-way from

$122
(JetBlue)

Popular in

April

Cheapest in

January

Average price

$225
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. 4% potential increase in price ($11 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 March 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 March 17, 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

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Tue 6/2

6:00 am-11:24 am

1 stop4h 24m

West Tisbury Martha's Vineyard

Sat 6/6

12:41 pm-8:14 pm

2 stops8h 33m

$293

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 6/13

9:33 am-3:23 pm

1 stop4h 50m

Nantucket Memorial

Sat 6/20

4:20 pm-8:44 pm

1 stop5h 24m

$422
Quickest round-trip

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 6/13

8:05 am-2:02 pm

1 stop4h 57m

Nantucket Memorial

Sat 6/20

12:16 pm-2:24 pm

Nonstop3h 08m

$488

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Fri 6/12

7:00 am-2:13 pm

1 stop6h 13m

Nantucket Memorial

Mon 6/22

11:11 am-5:27 pm

1 stop7h 16m

$518

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Thu 6/4

8:50 am-5:20 pm

1 stop7h 30m

Hyannis Barnstable

Tue 6/9

3:50 pm-7:35 pm

1 stop4h 45m

$557

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 3/25

11:00 am-5:20 pm

1 stop5h 20m

Hyannis Barnstable

Sun 3/29

12:07 pm-5:24 pm

1 stop6h 17m

$572

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 5/27

8:50 am-5:20 pm

1 stop7h 30m

Hyannis Barnstable

Sun 5/31

7:05 am-2:30 pm

2 stops8h 25m

$595

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Mon 6/8

8:50 am-2:40 pm

1 stop4h 50m

Hyannis Barnstable

Wed 6/17

10:29 am-7:25 pm

1 stop9h 56m

$642

ChicagoProvincetown

ORD - PVC

ORDPVC

Chicago O'Hare Intl

Thu 7/9

10:48 am-6:30 pm

1 stop6h 42m

Provincetown

Mon 7/13

2:20 pm-7:25 pm

1 stop6h 05m

$666

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Wed 3/25

11:00 am-6:50 pm

1 stop6h 50m

West Tisbury Martha's Vineyard

Sun 3/29

10:10 am-5:24 pm

1 stop8h 14m

$701

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/17

Showing 1-10 of 58 resultsSorted by cheapest first
1
2
3
...
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 March 17, 2026.
Read through reviews of airlines operating flights from Chicago to Cape Cod and the Islands, such as JetBlue and 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.
JetBlue
7.2
Good
2,906 reviews

Boarding

7.4

Food

6.6

Comfort

7.5

Crew

8.0

Overall

7.2

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.
JetBlue
7.2
Good
2,906 reviews
JetBlue
7.2
Good
2,906 reviews

Boarding

7.4

Food

6.6

Comfort

7.5

Crew

8.0

Overall

7.2

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.
American Airlines
7.1
Good
11,466 reviews
JetBlue
7.2
Good
2,906 reviews

Boarding

7.4

Food

6.6

Comfort

7.5

Crew

8.0

Overall

7.2

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

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 4h 24m. Delta provides one of the quickest options available for as low as $293. The distance from Chicago to Cape Cod and the Islands is about 891 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$123Average$572FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$319Average$522FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
Site
©2026 Cheapflights