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

ACK — CHI
Aug 5 — Aug 121
Wed 8/5
Wed 8/12
1 adult, Economy
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1. Tell us where you want to go

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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 July 6, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$190
(JetBlue)

One-way from

$79
(Priceline)

Popular in

June

Cheapest in

January

Average price

$240
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. 7% potential increase in price ($19 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 July 2026
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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 July 6, 2026.

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 $256, JetBlue can have you in Chicago from Cape Cod and the Islands in 6h 01m. The distance between Cape Cod and the Islands and Chicago is about 891 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 Hyannis Barnstable - Chicago O'Hare Intl, West Tisbury Martha's Vineyard - 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 (100%), Qatar Airways (100%) or Republic Airways (100%) 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 $354, our data shows the cheapest flight currently is $316. When looking at the most popular route, (Hyannis Barnstable - Chicago O'Hare Intl), you can expect to pay $199 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.

See more FAQs

Traveling to a place near Chicago?

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

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