HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

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

ACK — CHI
Sep 30 — Oct 71
Wed 9/30
Wed 10/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Cape Cod and the Islands to Chicago

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$530
(JetBlue)

One-way from

$271
(JetBlue)

Popular in

June

Cheapest in

January

Average price

$256
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. 6% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search 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?

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

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

    For as low as $530, JetBlue can have you in Chicago from Cape Cod and the Islands in 6h 47m. The distance between Cape Cod and the Islands and Chicago is about 891 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.

  • 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 $556, our data shows the cheapest flight currently is $263. When looking at the most popular route, (Hyannis Barnstable - Chicago O'Hare Intl), you can expect to pay $622 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
Lansing
Merrillville
Valparaiso
Hammond
Saint Joseph
Porter

Browse thousands of different options on Cheapflights for your next trip

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.