ORD

$96 Find Cheap Flights from Cape Cod and the Islands to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 8/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

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Flights Deals

Cheap Flights from Cape Cod and the Islands to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cape Cod and the Islands to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cape Cod and the Islands to Chicago

Fri, Aug 22 - Tue, Aug 26
JetBlue Logo
4:48 pm - 10:28 pmACK-ORD
6h 40m1 stop
JetBlue Logo
6:15 am - 11:53 amORD-ACK
4h 38m1 stop
$197JetBlue
Find Deal
Fri, Aug 22 - Tue, Aug 26
Delta Logo
3:26 pm - 9:53 pmACK-ORD
7h 27m1 stop
Delta Logo
6:00 am - 11:26 amORD-ACK
4h 26m1 stop
$238Delta
Find Deal
Fri, Aug 22 - Tue, Aug 26
Delta Logo
4:49 pm - 10:20 pmACK-ORD
6h 31m1 stop
Delta Logo
7:15 am - 4:09 pmORD-ACK
7h 54m2 stops
$244Delta
Find Deal
Fri, Aug 22 - Tue, Aug 26
Delta Logo
3:26 pm - 9:53 pmACK-ORD
7h 27m1 stop
Delta Logo
6:00 am - 11:26 amORD-ACK
4h 26m1 stop
$248Delta
Find Deal
Wed, Aug 13 - Sun, Aug 17
American Airlines Logo
1:44 pm - 5:52 pmHYA-ORD
5h 08m1 stop
American Airlines Logo
6:06 am - 1:51 pmORD-HYA
6h 45m1 stop
$343American Airlines
Find Deal
Wed, Aug 13 - Sun, Aug 17
American Airlines Logo
12:24 pm - 7:26 pmACK-ORD
8h 02m1 stop
American Airlines Logo
6:55 am - 1:04 pmORD-ACK
5h 09m1 stop
$363American Airlines
Find Deal
Wed, Aug 13 - Sun, Aug 17
United Airlines Logo
4:46 pm - 11:41 pmACK-ORD
7h 55m1 stop
United Airlines Logo
10:35 am - 2:29 pmORD-ACK
2h 54mnonstop
$636United Airlines
Find Deal
Wed, Aug 13 - Sun, Aug 17
Logo
1:01 pm - 10:22 pmHYA-ORD
10h 21m2 stops
Logo
10:12 am - 8:27 pmORD-HYA
9h 15m2 stops
$659
Find Deal
Mon, Aug 18 - Wed, Aug 20
Logo
2:34 pm - 10:22 pmMVY-ORD
32h 48m3 stops
Logo
8:12 pm - 6:40 amORD-MVY
33h 28m3 stops
$697
Find Deal
Thu, Aug 28 - Fri, Aug 29
United Airlines Logo
6:46 pm - 8:05 amACK-ORD
14h 19m2 stops
United Airlines Logo
9:15 pm - 9:48 amORD-ACK
11h 33m2 stops
$734United Airlines
Find Deal
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$96
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 13% lower on average.
Flight from West Tisbury to Chicago

FAQs for booking Cape Cod and the Islands to Chicago flights

  • How does KAYAK find such low prices on flights from Cape Cod and the Islands to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cape Cod and the Islands to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cape Cod and the Islands to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Cape Cod and the Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cape Cod and the Islands to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Cape Cod and the Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cape Cod and the Islands to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Cape Cod and the Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Chicago (ORD)

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