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

$157+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — ACK
Mar 8 — Mar 151
Sat 3/8
Sat 3/15
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

Keep the following information in mind while searching for Chicago to Cape Cod and the Islands flight deals. Data was last updated March 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$252
(JetBlue)

One-way from

$157
(JetBlue)
Provider with most accurate pricing for Chicago (CHI)-Nantucket Memorial flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Nantucket Memorial 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

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 March 3, 2025.

This JetBlue deal was found by Cheapflights users on 3/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/296:00 amORD - ACK
1 stop4h 53mJetBlue
Fri 7/44:34 pmACK - ORD
1 stop7h 51mJetBlue
Deal found 3/1$252
This American Airlines deal was found by Cheapflights users on 3/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/112:47 pmORD - ACK
1 stop3h 51mAmerican Airlines
Mon 8/45:26 pmACK - ORD
1 stop6h 58mAmerican Airlines
Deal found 3/3$278
This Delta deal was found by Cheapflights users on 3/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/317:00 amORD - ACK
1 stop5h 32mDelta
Wed 6/412:05 pmACK - ORD
1 stop6h 46mDelta
Deal found 3/2$358
This American Airlines deal was found by Cheapflights users on 3/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/121:50 pmORD - MVY
1 stop25h 54mAmerican Airlines
Sat 7/192:36 pmMVY - ORD
1 stop20h 29mAmerican Airlines
Deal found 3/3$386
This American Airlines deal was found by Cheapflights users on 3/2. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/25:00 amORD - HYA
1 stop6h 03mAmerican Airlines
Tue 7/812:33 pmHYA - ORD
1 stop5h 57mAmerican Airlines
Deal found 3/2$399
This Delta deal was found by Cheapflights users on 3/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/247:00 amORD - MVY
1 stop6h 28mDelta
Wed 5/2812:15 pmMVY - ORD
1 stop8h 05mDelta
Deal found 3/2$493
This JetBlue Airways deal was found by Cheapflights users on 3/2. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/185:26 pmORD - HYA
1 stop15h 44mMultiple Airlines
Sat 3/2211:25 amHYA - ORD
1 stop5h 40mMultiple Airlines
Deal found 3/2$494
This JetBlue deal was found by Cheapflights users on 3/2. 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.
Thu 7/318:40 amORD - HYA
1 stop6h 10mJetBlue
Tue 8/54:59 pmHYA - ORD
1 stop7h 26mJetBlue
Deal found 3/2$530
This JetBlue Airways deal was found by Cheapflights users on 3/1. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/141:15 pmORD - MVY
1 stop20h 15mMultiple Airlines
Tue 3/185:00 pmMVY - ORD
1 stop24h 30mMultiple Airlines
Deal found 3/1$589
This Mytrip deal was found by Cheapflights users on 3/1. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/136:45 amORD - ACK
2 stops32h 00mMultiple Airlines
Mon 3/174:55 pmACK - ORD
2 stops21h 44mMultiple Airlines
Deal found 3/1$589
This JetBlue deal was found by Cheapflights users on 3/1. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/48:50 amORD - PVC
1 stop7h 55mJetBlue
Wed 6/1111:40 amPVC - ORD
1 stop7h 52mJetBlue
Deal found 3/1$590
This JetBlue deal was found by Cheapflights users on 3/3. 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.
Wed 4/210:37 amORD - MVY
1 stop4h 53mJetBlue
Thu 4/311:30 amMVY - ORD
1 stop8h 45mJetBlue
Deal found 3/3$634

Find flights from Chicago to Cape Cod and the Islands within your budget

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 3, 2025.

Fly from

Chicago

Fly to

Cape Cod and the Islands

Route

Depart

Return

Price

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sun 6/29

6:00 am-11:53 am

1 stop4h 53m

Nantucket Memorial

Fri 7/4

4:34 pm-11:25 pm

1 stop7h 51m

$252

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Fri 8/1

12:47 pm-5:38 pm

1 stop3h 51m

Nantucket Memorial

Mon 8/4

5:26 pm-11:24 pm

1 stop6h 58m

$278

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Sat 5/31

7:00 am-1:32 pm

1 stop5h 32m

Nantucket Memorial

Wed 6/4

12:05 pm-5:51 pm

1 stop6h 46m

$358

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 7/12

1:50 pm-4:44 pm

1 stop25h 54m

West Tisbury Martha's Vineyard

Sat 7/19

2:36 pm-10:05 am

1 stop20h 29m

$386

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Wed 7/2

5:00 am-12:03 pm

1 stop6h 03m

Hyannis Barnstable

Tue 7/8

12:33 pm-5:30 pm

1 stop5h 57m

$399

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Sat 5/24

7:00 am-2:28 pm

1 stop6h 28m

West Tisbury Martha's Vineyard

Wed 5/28

12:15 pm-7:20 pm

1 stop8h 05m

$493

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Tue 3/18

5:26 pm-10:10 am

1 stop15h 44m

Hyannis Barnstable

Sat 3/22

11:25 am-4:05 pm

1 stop5h 40m

$494

ChicagoHyannis

ORD - HYA

ORDHYA

Chicago O'Hare Intl

Thu 7/31

8:40 am-3:50 pm

1 stop6h 10m

Hyannis Barnstable

Tue 8/5

4:59 pm-11:25 pm

1 stop7h 26m

$530

ChicagoWest Tisbury

ORD - MVY

ORDMVY

Chicago O'Hare Intl

Fri 3/14

1:15 pm-10:30 am

1 stop20h 15m

West Tisbury Martha's Vineyard

Tue 3/18

5:00 pm-4:30 pm

1 stop24h 30m

$589

ChicagoNantucket

ORD - ACK

ORDACK

Chicago O'Hare Intl

Thu 3/13

6:45 am-3:45 pm

2 stops32h 00m

Nantucket Memorial

Mon 3/17

4:55 pm-1:39 pm

2 stops21h 44m

$589

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/2

Showing 1-10 of 27 results
1
2
3

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.

Travel insights for flights from Chicago to Cape Cod and the Islands

Get recent, data-driven insights about flights from Chicago to Cape Cod and the Islands including ideal travel times, pricing trends, and more.

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 March 3, 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.

Rainfall in Cape Cod and the Islands by month

Plan your trip to Cape Cod and the Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Cape Cod and the Islands ranges from 1.6 - 4.3 inches per month. January is typically the wettest month, when rainfall can reach 4.3 in. June is typically the driest time to visit Cape Cod and the Islands when rainfall is around 1.6 in.

Temperature in Cape Cod and the Islands by month

Plan your trip to Cape Cod and the Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Cape Cod and the Islands, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 66.2 F. Travelers looking to avoid the cold should look outside of February, when temperatures are typically at their lowest (around 32.0 F).

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 3, 2025.
Read reviews from past customers who have flown Delta, United Airlines and JetBlue from Chicago to Cape Cod and the Islands. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
8,068 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta
8.0
Very good
8,068 reviews
Delta
8.0
Very good
8,068 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines
7.4
Good
8,679 reviews
Delta
8.0
Very good
8,068 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

JetBlue
7.4
Good
3,008 reviews
Delta
8.0
Very good
8,068 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
8,068 reviews

Boarding

8.2

Entertainment

7.9

Comfort

8.0

Food

7.3

Overall

8.0

Crew

8.5

Reviews

1 / 20

10.0
Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 $157. 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 O'Hare Intl - Hyannis Barnstable.

  • 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 $549, our data indicates the cheapest price to be $549. The most popular route (Chicago O'Hare Intl - Nantucket Memorial), is priced around $252.

  • 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.

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.
O'Hare Intl to Boston flights
O'Hare Intl to Hartford flights
St. Louis to Boston flights
O'Hare Intl to Albany flights
Midway to Boston flights
Midway to Hartford flights
Midway to Albany flights
Moline to Boston flights
O'Hare Intl to Worcester flights
O'Hare Intl to Nantucket flights
St. Louis to Hartford flights
O'Hare Intl to West Tisbury flights
St. Louis to Albany flights
Peoria to Boston flights
Peoria to Hartford flights
Decatur to Boston flights
Moline to Hartford flights
O'Hare Intl to Hyannis flights
Champaign to Boston flights
Bloomington to Boston flights
Peoria to Albany flights
O'Hare Intl to Provincetown flights
Evansville to Boston flights
Bloomington to Albany flights
Springfield to Boston flights
St. Louis to West Tisbury flights
Moline to Albany flights
Midway to Nantucket flights
Evansville to Hartford flights
Springfield to Hartford flights
Dubuque to Boston flights
Dubuque to Hartford flights
O'Hare Intl to New Bedford flights
Champaign to Hartford flights
Champaign to Albany flights
Bloomington to Hartford flights

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 March 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$230Average$573FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$230Average$489FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$469Average$598FlexibilityNo cancel feeOn-time69%
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.