ORD

$101 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 8/5. 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, 0 bags

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Everything you should know

Cheapest round-trip
$500
JetBlue
Sat 7/11Wed 7/15
HYA - ORD • 1 stop
Cheapest one-way
$101
JetBlue
Wed 8/5
MVY - ORD • 1 stop
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Flight Deals
Useful Info
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

Sat, Jul 11 - Wed, Jul 15
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$500JetBlue
Mon, Jul 13 - Thu, Jul 16
JetBlue Logo
4:55 pm - 8:44 pm
MVY
-
ORD
4h 49m
1 stop
JetBlue Logo
9:33 am - 4:00 pm
ORD
-
MVY
5h 27m
1 stop
$557JetBlue
Thu, Jun 18 - Mon, Jun 22
Delta Logo
12:15 pm - 5:48 pm
MVY
-
ORD
6h 33m
1 stop
Delta Logo
10:35 am - 4:17 pm
ORD
-
MVY
4h 42m
1 stop
$588Delta
Fri, May 22 - Mon, May 25
Delta Logo
4:02 pm - 10:36 pm
MVY
-
ORD
7h 34m
1 stop
Delta Logo
7:05 am - 3:22 pm
ORD
-
MVY
7h 17m
1 stop
$598Delta
Tue, Jul 7 - Mon, Jul 13
JetBlue Logo
4:55 pm - 8:44 pm
MVY
-
ORD
4h 49m
1 stop
JetBlue Logo
9:33 am - 4:00 pm
ORD
-
MVY
5h 27m
1 stop
$616JetBlue
Mon, Jul 13 - Thu, Jul 16
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$649JetBlue
Sun, Aug 2 - Thu, Aug 6
JetBlue Logo
4:55 pm - 8:44 pm
MVY
-
ORD
4h 49m
1 stop
JetBlue Logo
9:33 am - 4:00 pm
ORD
-
MVY
5h 27m
1 stop
$688JetBlue
Fri, Apr 24 - Sun, Apr 26
Multiple Airlines Logo
2:54 pm - 9:36 pm
ACK
-
ORD
7h 42m
1 stop
Multiple Airlines Logo
9:41 am - 3:50 pm
ORD
-
ACK
5h 09m
1 stop
$708Multiple Airlines
Tue, Jul 7 - Mon, Jul 13
JetBlue Logo
4:20 pm - 8:44 pm
HYA
-
ORD
5h 24m
1 stop
JetBlue Logo
9:33 am - 3:17 pm
ORD
-
HYA
4h 44m
1 stop
$804JetBlue
Fri, May 22 - Tue, May 26
Delta Logo
1:18 pm - 5:35 pm
MVY
-
ORD
5h 17m
1 stop
Delta Logo
6:00 am - 11:24 am
ORD
-
MVY
4h 24m
1 stop
$878Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$101
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 2% increase in price.
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
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Des Plaines
Hoffman Estates
Hammond
Willowbrook
Portage
South Holland
Delavan
Northbrook
Lansing
Pleasant Prairie
Elmhurst
Lisle
Valparaiso

Everything you need to know for your flight to Chicago

Information on your arrival and departure airports

Chicago (ORD)