ORD

$136 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 10/11. 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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Flight 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

Sun, Feb 22 - Wed, Feb 25
JetBlue Logo
12:07 pm - 5:31 pmHYA-ORD
6h 24m1 stop
JetBlue Logo
12:10 pm - 6:39 pmORD-HYA
5h 29m1 stop
$410JetBlue
Find Deal
Sun, Nov 9 - Tue, Nov 11
JetBlue Logo
6:45 am - 10:35 amPVC-ORD
4h 50m1 stop
JetBlue Logo
11:20 am - 5:38 pmORD-PVC
5h 18m1 stop
$460JetBlue
Find Deal
Fri, Sep 26 - Sun, Sep 28
JetBlue Logo
12:00 pm - 6:55 pmPVC-ORD
7h 55m1 stop
JetBlue Logo
9:51 am - 5:26 pmORD-PVC
6h 35m1 stop
$470JetBlue
Find Deal
Fri, Dec 12 - Mon, Dec 15
JetBlue Logo
12:07 pm - 7:43 pmHYA-ORD
8h 36m1 stop
JetBlue Logo
11:25 am - 6:39 pmORD-HYA
6h 14m1 stop
$555JetBlue
Find Deal
Fri, Sep 26 - Sun, Sep 28
JetBlue Logo
5:30 pm - 8:56 amACK-ORD
16h 26m1 stop
JetBlue Logo
9:51 am - 8:00 pmORD-ACK
9h 09m1 stop
$568JetBlue
Find Deal
Fri, Nov 7 - Tue, Nov 11
JetBlue Logo
6:45 am - 10:35 amPVC-ORD
4h 50m1 stop
JetBlue Logo
11:20 am - 5:38 pmORD-PVC
5h 18m1 stop
$595JetBlue
Find Deal
Fri, Nov 21 - Sun, Nov 23
JetBlue Logo
12:07 pm - 8:03 pmHYA-ORD
8h 56m1 stop
JetBlue Logo
1:20 pm - 6:39 pmORD-HYA
4h 19m1 stop
$645JetBlue
Find Deal
Sun, Oct 26 - Tue, Oct 28
JetBlue Logo
12:07 pm - 5:55 pmHYA-ORD
6h 48m1 stop
JetBlue Logo
11:20 am - 6:39 pmORD-HYA
6h 19m1 stop
$685JetBlue
Find Deal
Wed, Oct 8 - Fri, Oct 10
Multiple Airlines Logo
8:15 am - 2:25 pmEWB-ORD
7h 10m1 stop
Multiple Airlines Logo
2:20 pm - 1:35 pmORD-EWB
22h 15m1 stop
$699Multiple Airlines
Find Deal
Fri, Sep 26 - Sun, Sep 28
Multiple Airlines Logo
8:35 am - 6:36 pmACK-ORD
11h 01m2 stops
Multiple Airlines Logo
6:33 pm - 3:13 pmORD-ACK
19h 40m2 stops
$1,256Multiple Airlines
Find Deal

Everything you should know

Cheapest round-trip
$410
JetBlue
Sun 2/22Wed 2/25
HYA - ORD • 1 stop
Cheapest one-way
$136
JetBlue
Sat 10/11
MVY - ORD • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$136
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 6% 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Gurnee
South Haven
Oak Brook
Merrillville
Saint Joseph
Tinley Park
Elk Grove Village
Hoffman Estates
Des Plaines
Hammond
Willowbrook
Portage
Delavan
Northbrook
Elmhurst
South Holland
Lisle
Pleasant Prairie
Valparaiso
Lansing

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Chicago (ORD)

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