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$113+ Cheap flights from Cape Cod and the Islands to Chicago (CHI)

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 9/18. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Aug 27 — Sep 31
Wed 8/27
Wed 9/3
1 adult, Economy
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Cheap flight deals from Cape Cod and the Islands to Chicago

Keep the following information in mind while searching for Cape Cod and the Islands to Chicago flight deals. Data was last updated August 22, 2025.

Round-trip from

$358
(Delta)

One-way from

$113
(JetBlue)

Popular in

March

Cheapest in

September

Average price

$223
From Cape Cod and the Islands to Chicago (CHI)
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One-way flight from Cape Cod and the Islands to Chicago (CHI)
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Highest demand for flights based on searches. 8% potential increase in price ($20 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 August 2025
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Find flight deals from Cape Cod and the Islands to Chicago

Cheapest flights from Cape Cod and the Islands to Chicago
Explore the most affordable flight options available from Cape Cod and the Islands to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 22, 2025.

This American Airlines deal was found by Cheapflights users on 8/20. 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 8/233:25 pmHYA - ORD
Nonstop3h 06mAmerican Airlines
Tue 8/265:00 amORD - HYA
1 stop5h 40mAmerican Airlines
Deal found 8/20$296
This Delta deal was found by Cheapflights users on 8/20. 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.
Fri 8/294:49 pmACK - ORD
1 stop6h 31mDelta
Tue 9/26:00 amORD - ACK
1 stop4h 26mDelta
Deal found 8/20$358
This Delta deal was found by Cheapflights users on 8/18. 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.
Fri 8/223:26 pmACK - ORD
1 stop7h 27mDelta
Tue 8/2610:30 amORD - ACK
1 stop4h 39mDelta
Deal found 8/18$368
This Delta deal was found by Cheapflights users on 8/19. 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.
Wed 8/2712:06 pmACK - ORD
1 stop6h 56mDelta
Fri 9/57:00 amORD - ACK
1 stop6h 46mDelta
Deal found 8/19$488
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Wed 8/276:46 pmACK - ORD
2 stops14h 19mUnited Airlines
Fri 9/59:37 pmORD - ACK
2 stops16h 34mUnited Airlines
Deal found 8/19$530
This Expedia deal was found by Cheapflights users on 8/19. 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.
Wed 8/2712:50 pmACK - ORD
1 stop10h 38mJetBlue
Fri 9/56:59 pmORD - ACK
2 stops15h 01mJetBlue
Deal found 8/19$532
This United deal was found by Cheapflights users on 8/21. 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.
Tue 9/26:48 amHYA - ORD
1 stop26h 17mMultiple Airlines
Tue 9/911:05 amORD - HYA
1 stop8h 22mMultiple Airlines
Deal found 8/21$545
This United deal was found by Cheapflights users on 8/21. 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.
Tue 9/168:56 amPVC - ORD
1 stop6h 24mMultiple Airlines
Fri 9/199:15 pmORD - PVC
1 stop11h 32mMultiple Airlines
Deal found 8/21$585
This JetBlue deal was found by Cheapflights users on 8/21. 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 9/2011:31 amMVY - ORD
1 stop7h 52mJetBlue
Sat 9/279:51 amORD - MVY
1 stop6h 24mJetBlue
Deal found 8/21$610
This Expedia deal was found by Cheapflights users on 8/20. 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.
Thu 9/410:17 amMVY - ORD
1 stop8h 37mJetBlue
Mon 9/87:50 pmORD - MVY
1 stop11h 15mJetBlue
Deal found 8/20$614
This Trip.com deal was found by Cheapflights users on 8/21. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/25:15 pmHYA - ORD
1 stop6h 13mJetBlue
Wed 9/39:42 amORD - HYA
1 stop6h 56mJetBlue
Deal found 8/21$621
This Mytrip deal was found by Cheapflights users on 8/20. 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 9/412:35 pmMVY - ORD
3 stops34h 23mMultiple Airlines
Mon 9/811:57 amORD - MVY
3 stops41h 43mMultiple Airlines
Deal found 8/20$725

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cape Cod and the Islands to Chicago 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 August 22, 2025.
Use the filters below to find and compare flights from Cape Cod and the Islands to Chicago that are best for you.

Fly from

Cape Cod and the Islands

Fly to

Chicago

Route

Depart

Return

Price

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 8/29

4:49 pm-10:20 pm

1 stop6h 31m

Chicago O'Hare Intl

Tue 9/2

6:00 am-11:26 am

1 stop4h 26m

$358

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 8/27

12:06 pm-6:02 pm

1 stop6h 56m

Chicago O'Hare Intl

Fri 9/5

7:00 am-2:46 pm

1 stop6h 46m

$488

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 8/27

6:46 pm-8:05 am

2 stops14h 19m

Chicago O'Hare Intl

Fri 9/5

9:37 pm-3:11 pm

2 stops16h 34m

$530

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 8/27

12:50 pm-10:28 pm

1 stop10h 38m

Chicago O'Hare Intl

Fri 9/5

6:59 pm-11:00 am

2 stops15h 01m

$532

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 9/2

6:48 am-8:05 am

1 stop26h 17m

Chicago O'Hare Intl

Tue 9/9

11:05 am-8:27 pm

1 stop8h 22m

$545

ProvincetownChicago

PVC - ORD

PVCORD

Provincetown

Tue 9/16

8:56 am-2:20 pm

1 stop6h 24m

Chicago O'Hare Intl

Fri 9/19

9:15 pm-9:47 am

1 stop11h 32m

$585

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Sat 9/20

11:31 am-6:23 pm

1 stop7h 52m

Chicago O'Hare Intl

Sat 9/27

9:51 am-5:15 pm

1 stop6h 24m

$610

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 9/4

10:17 am-5:54 pm

1 stop8h 37m

Chicago O'Hare Intl

Mon 9/8

7:50 pm-8:05 am

1 stop11h 15m

$614

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 9/2

5:15 pm-10:28 pm

1 stop6h 13m

Chicago O'Hare Intl

Wed 9/3

9:42 am-5:38 pm

1 stop6h 56m

$621

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 9/4

9:40 am-9:58 pm

2 stops13h 18m

Chicago O'Hare Intl

Mon 9/8

11:57 am-12:06 pm

2 stops23h 09m

$628

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 54 results
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Best time to book a flight from Cape Cod and the Islands to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Cape Cod and the Islands 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 Cape Cod and the Islands to Chicago

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

Find hourly flight availability from Cape Cod and the Islands to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 22, 2025.

When flying from Cape Cod and the Islands to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Related info for your journey

Find useful and relevant information for your journey from Cape Cod and the Islands to Chicago. 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 Cape Cod and the Islands to Chicago?

    For as low as $358, Delta can have you in Chicago from Cape Cod and the Islands in 6h 31m. The distance between Cape Cod and the Islands and Chicago 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 Cape Cod and the Islands to Chicago?

    The most popular flight routes from Cape Cod and the Islands to Chicago are West Tisbury Martha's Vineyard - Chicago O'Hare Intl, Hyannis Barnstable - Chicago O'Hare Intl and Nantucket Memorial - Chicago O'Hare Intl.

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

    No one likes to see their flight delayed. When booking a flight from Cape Cod and the Islands to Chicago consider choosing American Airlines (64%), Republic Airways (64%) or SkyWest Airlines (43%) as they are the most reliable in getting you off to your destination on time.

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

    While on average a flight from Cape Cod and the Islands to Chicago is generally $633, our data shows the cheapest flight currently is $456. When looking at the most popular route, (West Tisbury Martha's Vineyard - Chicago O'Hare Intl), you can expect to pay $614 for that flight.

  • Can I find deals for flights from Cape Cod and the Islands to Chicago that include hotel bookings?

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

  • How can I find direct flights from Cape Cod and the Islands to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cape Cod and the Islands to Chicago.

  • Can I find deals for business class flights from Cape Cod and the Islands to Chicago?

    Yes. Cheapflights offers flight deals from Cape Cod and the Islands to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Cape Cod and the Islands to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Cape Cod and the Islands to Chicago (average of $245). Flying from Cape Cod and the Islands to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Alternative routes for Cape Cod and the Islands to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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