How long is the flight from Cape Cod and the Islands to Chicago?

For as low as $425, JetBlue can have you in Chicago from Cape Cod and the Islands in 6h 37m. The distance between Cape Cod and the Islands and Chicago is about 905 mi.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, 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 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 Nantucket Memorial - Chicago O'Hare Intl, West Tisbury Martha's Vineyard - Chicago O'Hare Intl and New Bedford Regional - Chicago O'Hare Intl.

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

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.

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.

$119+ Flights from Cape Cod and the Islands to Chicago

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Cheap flight deals from Cape Cod and the Islands to Chicago

Best flights from Cape Cod and the Islands to Chicago
Discover carefully curated flight deals from Cape Cod and the Islands to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

Tue 2/1012:07 pmHYA - ORD

1 stop6h 37mJetBlue

Sun 2/1510:00 amORD - HYA

1 stop6h 20mJetBlue

Deal found 12/14

$425

Thu 1/11:28 pmMVY - ORD

1 stop6h 18mMultiple Airlines

Mon 1/56:45 amORD - MVY

2 stops11h 05mMultiple Airlines

Deal found 12/17

$883

Fri 2/61:28 pmMVY - ORD

1 stop5h 16mJetBlue

Mon 2/97:45 amORD - MVY

1 stop6h 50mJetBlue

Deal found 12/17

$634

Last-minute flights from Cape Cod and the Islands to Chicago
Discover last-minute flight deals from Cape Cod and the Islands to Chicago. Data last updated December 18, 2025 and is based on user searches.

Thu 1/11:28 pmMVY - ORD

1 stop6h 18mMultiple Airlines

Mon 1/56:45 amORD - MVY

2 stops11h 05mMultiple Airlines

Deal found 12/17

$883

Fri 1/212:07 pmHYA - ORD

1 stop7h 39mMultiple Airlines

Tue 1/610:55 amORD - HYA

1 stop5h 25mMultiple Airlines

Deal found 12/17

$470

One-way flights from Cape Cod and the Islands to Chicago
Search for one-way flight options from Cape Cod and the Islands to Chicago. Find affordable one-way fares based on user searches. Data last updated December 18, 2025.

Sat 6/1310:00 amACK - ORD

2 stops11h 24mDelta

Deal found 12/17

$119

Wed 1/147:05 amHYA - ORD

2 stops26h 13mMultiple Airlines

Deal found 12/17

$179

Thu 1/157:05 amHYA - ORD

2 stops13h 36mMultiple Airlines

Deal found 12/15

$185

Sat 1/1712:07 pmHYA - ORD

1 stop6h 36mJetBlue

Deal found 12/14

$188

Mon 2/212:07 pmHYA - ORD

1 stop6h 36mJetBlue

Deal found 12/17

$193

Mon 3/1612:07 pmHYA - ORD

1 stop6h 17mJetBlue

Deal found 12/15

$198

Sun 1/1812:07 pmHYA - ORD

2 stops50h 06mMultiple Airlines

Deal found 12/15

$199

Thu 3/1912:07 pmHYA - ORD

1 stop6h 17mJetBlue

Deal found 12/17

$203

Fri 6/121:45 pmACK - ORD

1 stop8h 00mDelta

Deal found 12/15

$204

Mon 1/127:05 amHYA - ORD

3 stops30h 03mMultiple Airlines

Deal found 12/15

$210

Tue 6/164:59 pmMVY - ORD

2 stops26h 42mDelta

Deal found 12/16

$216

Sat 6/134:32 pmACK - ORD

Nonstop3h 18mUnited Airlines

Deal found 12/15

$235

Find flight deals from Cape Cod and the Islands to Chicago

Most accurate provider	Mytrip 3 stars
Most trusted provider	Mytrip 3 stars
Round-trip from	$425 (JetBlue)
One-way from	$119 (Delta)
Popular in	April
Cheapest in	September
Average price	$253

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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. 0% potential price decrease ($2 potential savings vs. average RT price).

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Average for round-trip flights in December 2025

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Cheapflights Fare Finder

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

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Tue 2/10

12:07 pm-5:44 pm

1 stop6h 37m

Chicago O'Hare Intl

Sun 2/15

10:00 am-5:20 pm

1 stop6h 20m

$425

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Fri 2/6

1:28 pm-5:44 pm

1 stop5h 16m

Chicago O'Hare Intl

Mon 2/9

7:45 am-3:35 pm

1 stop6h 50m

$634

West TisburyChicago

MVY - ORD

MVYORD

West Tisbury Martha's Vineyard

Thu 1/1

1:28 pm-6:46 pm

1 stop6h 18m

Chicago O'Hare Intl

Mon 1/5

6:45 am-6:50 pm

2 stops11h 05m

$883

NantucketChicago

ACK - ORD

ACKORD

Nantucket Memorial

Sat 6/13

10:00 am-8:24 pm

2 stops11h 24m

$119

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Sat 1/17

12:07 pm-5:43 pm

1 stop6h 36m

$188

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 1/12

12:07 pm-4:52 pm

2 stops29h 45m

$188

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 1/19

7:05 am-1:57 pm

2 stops31h 52m

$188

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Wed 1/14

7:05 am-7:41 pm

2 stops37h 36m

$189

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Mon 2/2

12:07 pm-5:43 pm

1 stop6h 36m

$193

HyannisChicago

HYA - ORD

HYAORD

Hyannis Barnstable

Thu 1/15

7:05 am-5:43 pm

1 stop11h 38m

$198

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 25 results

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

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Related info for your journey

How long is the flight from Cape Cod and the Islands to Chicago?
For as low as $425, JetBlue can have you in Chicago from Cape Cod and the Islands in 6h 37m. 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 Nantucket Memorial - Chicago O'Hare Intl, West Tisbury Martha's Vineyard - Chicago O'Hare Intl and New Bedford Regional - 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.

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Benton Harbor

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$119+ 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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.

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

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Cape Cod and the Islands to Chicago

Best flights from Cape Cod and the Islands to ChicagoDiscover carefully curated flight deals from Cape Cod and the Islands to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

Discover carefully curated flight deals from Cape Cod and the Islands to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

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 December 18, 2025.

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

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

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.

Cheapflights Insights

Everything you need to know about your flight from Cape Cod and the Islands to Chicago

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?

What are the most popular routes from Cape Cod and the Islands to Chicago?

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

How can I 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?

Traveling to a place near Chicago?

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Best flights from Cape Cod and the Islands to Chicago
Discover carefully curated flight deals from Cape Cod and the Islands to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.