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$173+ 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
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 November 3, 2025.

Most accurate provider

Mytrip
3 stars

Most trusted provider

Mytrip
3 stars

Round-trip from

$465
(JetBlue)

One-way from

$173
(Trip.com)

Popular in

April

Cheapest in

September

Average price

$248
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
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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. 9% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 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 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 November 3, 2025.

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.
Fri 11/1412:07 pmHYA - ORD
1 stop6h 48mJetBlue
Mon 11/1711:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 11/3$535
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 11/188:15 amEWB - ORD
3 stops28h 15mMultiple Airlines
Sat 11/226:48 amORD - EWB
2 stops11h 27mMultiple Airlines
Deal found 11/3$546
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.
Fri 11/1412:07 pmHYA - ORD
1 stop6h 48mJetBlue
Sun 11/1611:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 11/3$555
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.
Thu 12/1112:07 pmHYA - ORD
1 stop8h 36mJetBlue
Sun 12/1411:25 amORD - HYA
1 stop6h 14mJetBlue
Deal found 11/2$600
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.
Wed 12/3112:07 pmHYA - ORD
1 stop7h 39mJetBlue
Sat 1/36:45 amORD - HYA
1 stop5h 25mJetBlue
Deal found 11/3$617
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.
Wed 11/512:07 pmHYA - ORD
1 stop6h 48mJetBlue
Fri 11/711:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 11/3$785
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 11/512:07 pmHYA - ORD
1 stop6h 48mJetBlue
Sat 11/86:45 amORD - HYA
1 stop5h 25mJetBlue
Deal found 11/2$853
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.
Fri 11/141:34 pmMVY - ORD
1 stop5h 21mJetBlue
Mon 11/176:45 amORD - MVY
1 stop5h 38mJetBlue
Deal found 11/3$859
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 11/712:07 pmHYA - ORD
1 stop6h 48mJetBlue
Sun 11/911:20 amORD - HYA
1 stop6h 19mJetBlue
Deal found 11/2$915
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.
Fri 11/141:34 pmMVY - ORD
1 stop5h 21mJetBlue
Sun 11/166:45 amORD - MVY
1 stop5h 38mJetBlue
Deal found 11/3$915
This JetBlue deal was found by Cheapflights users on 11/1. 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 11/511:40 amMVY - ORD
1 stop7h 15mJetBlue
Sat 11/810:00 amORD - MVY
1 stop4h 50mJetBlue
Deal found 11/1$934
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/189:52 amMVY - ORD
1 stop27h 53mMultiple Airlines
Sat 11/2210:22 amORD - MVY
2 stops22h 27mMultiple Airlines
Deal found 11/3$985

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 November 3, 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

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 3/16

12:07 pm-5:31 pm

1 stop6h 24m

Chicago O'Hare Intl

Wed 3/18

12:10 pm-6:39 pm

1 stop5h 29m

$465

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/14

12:07 pm-5:55 pm

1 stop6h 48m

Chicago O'Hare Intl

Mon 11/17

11:20 am-6:39 pm

1 stop6h 19m

$535

New BedfordChicago

EWB - ORD

EWBORD

New Bedford Regional

Tue 11/18

8:15 am-11:30 am

3 stops28h 15m

Chicago O'Hare Intl

Sat 11/22

6:48 am-7:15 pm

2 stops11h 27m

$546

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 11/14

12:07 pm-5:55 pm

1 stop6h 48m

Chicago O'Hare Intl

Sun 11/16

11:20 am-6:39 pm

1 stop6h 19m

$555

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 12/11

12:07 pm-7:43 pm

1 stop8h 36m

Chicago O'Hare Intl

Sun 12/14

11:25 am-6:39 pm

1 stop6h 14m

$600

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 12/31

12:07 pm-6:46 pm

1 stop7h 39m

Chicago O'Hare Intl

Sat 1/3

6:45 am-1:10 pm

1 stop5h 25m

$617

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 11/14

1:34 pm-5:55 pm

1 stop5h 21m

Chicago O'Hare Intl

Mon 11/17

6:45 am-1:23 pm

1 stop5h 38m

$859

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 11/14

1:34 pm-5:55 pm

1 stop5h 21m

Chicago O'Hare Intl

Sun 11/16

6:45 am-1:23 pm

1 stop5h 38m

$915

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Tue 11/18

9:52 am-12:45 pm

1 stop27h 53m

Chicago O'Hare Intl

Sat 11/22

10:22 am-9:49 am

2 stops22h 27m

$985

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 1/1

12:07 pm-6:46 pm

1 stop7h 39m

$173

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 39 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
No data available for this route at this time. Please check back soon.

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 $465, JetBlue can have you in Chicago from Cape Cod and the Islands in 6h 24m. The distance between Cape Cod and the Islands and Chicago is about 905 mi.

  • 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 Hyannis Barnstable - Chicago O'Hare Intl, West Tisbury Martha's Vineyard - Chicago O'Hare Intl and Nantucket Memorial - Chicago O'Hare Intl.

  • 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.

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
Porter
Benton Harbor

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Alternative routes for Cape Cod and the Islands to Chicago

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