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$132+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
ACK — CHI
Jun 3 — Jun 101
Wed 6/3
Wed 6/10
1 adult, Economy
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Cheap 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 May 4, 2026.

This Delta deal was found by Cheapflights users on 4/30. 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 7/223:24 pm
ACK
-
ORD
1 stop7h 28m
Delta
Mon 7/279:30 am
ORD
-
ACK
1 stop5h 18m
Delta
Deal found 4/30$290
This American Airlines deal was found by Cheapflights users on 5/3. 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 7/183:10 pm
ACK
-
ORD
1 stop7h 32m
American Airlines
Sat 7/258:29 pm
ORD
-
ACK
1 stop12h 45m
American Airlines
Deal found 5/3$337
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:03 pm
HYA
-
ORD
1 stop7h 34m
American Airlines
Tue 8/187:00 am
ORD
-
HYA
1 stop5h 13m
American Airlines
Deal found 5/1$345
This Delta deal was found by Cheapflights users on 5/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2110:00 am
ACK
-
ORD
2 stops11h 17m
Delta
Sun 8/236:00 am
ORD
-
ACK
1 stop6h 27m
Delta
Deal found 5/1$359
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:03 pm
HYA
-
ORD
1 stop5h 38m
American Airlines
Thu 8/205:00 am
ORD
-
HYA
1 stop6h 12m
American Airlines
Deal found 5/1$365
This JetBlue deal was found by Cheapflights users on 4/29. 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 7/112:15 pm
ACK
-
ORD
1 stop6h 06m
JetBlue
Sat 7/46:00 am
ORD
-
ACK
1 stop8h 34m
JetBlue
Deal found 4/29$377
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:59 pm
HYA
-
ORD
1 stop6h 38m
American Airlines
Mon 8/248:05 am
ORD
-
HYA
1 stop4h 08m
American Airlines
Deal found 5/1$385
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:59 pm
HYA
-
ORD
1 stop6h 38m
American Airlines
Sat 8/225:00 am
ORD
-
HYA
1 stop6h 12m
American Airlines
Deal found 5/1$390
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:03 pm
HYA
-
ORD
1 stop5h 38m
American Airlines
Sat 8/2211:15 am
ORD
-
HYA
Nonstop2h 44m
American Airlines
Deal found 5/1$406
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/175:59 pm
HYA
-
ORD
1 stop6h 38m
American Airlines
Mon 8/248:05 am
ORD
-
HYA
1 stop4h 08m
American Airlines
Deal found 5/1$410
This JetBlue deal was found by Cheapflights users on 5/2. 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.
Tue 7/144:23 pm
HYA
-
ORD
1 stop6h 32m
JetBlue
Wed 7/156:00 am
ORD
-
HYA
1 stop8h 11m
JetBlue
Deal found 5/2$413
This American Airlines deal was found by Cheapflights users on 5/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:59 pm
HYA
-
ORD
1 stop5h 31m
American Airlines
Sat 8/2211:15 am
ORD
-
HYA
Nonstop2h 44m
American Airlines
Deal found 5/1$426

Find 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 May 4, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$290
(Delta)

One-way from

$132
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$243
Provider with most accurate pricing for Boston Logan Intl-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-Chicago (CHI) flights.
Search Deals
From Cape Cod and the Islands to Chicago (CHI)
Search Deals
One-way flight from Cape Cod and the Islands to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2026
Search Deals

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 May 4, 2026.
Use the filters below to find and compare flights from Cape Cod and the Islands to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 7/22

12:13 pm-4:30 pm

1 stop5h 17m

Chicago O'Hare Intl

Mon 7/27

9:30 am-3:48 pm

1 stop5h 18m

$290

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Fri 8/21

10:00 am-8:17 pm

2 stops11h 17m

Chicago O'Hare Intl

Sun 8/23

6:00 am-1:27 pm

1 stop6h 27m

$359

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 7/1

4:30 pm-9:29 pm

1 stop5h 59m

Chicago O'Hare Intl

Sat 7/4

6:00 am-3:34 pm

1 stop8h 34m

$392

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 8/17

5:59 pm-11:37 pm

1 stop6h 38m

Chicago O'Hare Intl

Mon 8/24

8:05 am-1:13 pm

1 stop4h 08m

$410

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 7/14

4:23 pm-9:55 pm

1 stop6h 32m

Chicago O'Hare Intl

Wed 7/15

6:00 am-3:11 pm

1 stop8h 11m

$413

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Fri 8/14

5:59 pm-11:59 pm

1 stop7h 00m

Chicago O'Hare Intl

Wed 8/19

8:05 am-1:13 pm

1 stop4h 08m

$433

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 8/19

5:59 pm-10:30 pm

1 stop5h 31m

Chicago O'Hare Intl

Fri 8/21

6:34 am-12:12 pm

1 stop4h 38m

$449

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 7/11

4:53 pm-9:55 pm

1 stop6h 02m

Chicago O'Hare Intl

Mon 7/13

6:00 am-3:11 pm

1 stop8h 11m

$459
Quickest round-trip

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Wed 7/1

3:44 pm-9:00 pm

1 stop6h 16m

Chicago O'Hare Intl

Sat 7/4

11:45 am-3:41 pm

Nonstop2h 56m

$468

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Sat 5/23

12:41 pm-7:09 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 5/25

6:07 am-12:39 pm

1 stop5h 32m

$469

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/3

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $290, Delta can have you in Chicago from Cape Cod and the Islands in 5h 17m. 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.

  • 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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