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.

$138 CHEAP FLIGHTS from Cape Cod and the Islands to Chicago (ORD)

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Flight Deals

Cheap Flights from Cape Cod and the Islands to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

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

Sun, Sep 6 - Sun, Sep 20

4:45 pm - 7:00 pmACK Nantucket Memorial-ORD Chicago O'Hare Intl

3h 15mnonstop

11:59 am - 3:49 pmORD Chicago O'Hare Intl-ACK Nantucket Memorial

2h 50mnonstop

$289United Airlines

Sat, Oct 3 - Sun, Oct 4

4:00 pm - 9:58 pmMVY West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl

6h 58m1 stop New York John F Kennedy Intl

7:00 am - 3:04 pmORD Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard

7h 04m1 stop New York John F Kennedy Intl

$302JetBlue

Fri, Sep 25 - Sun, Sep 27

4:00 pm - 9:58 pmMVY West Tisbury Martha's Vineyard-ORD Chicago O'Hare Intl

6h 58m1 stop New York John F Kennedy Intl

7:00 am - 3:04 pmORD Chicago O'Hare Intl-MVY West Tisbury Martha's Vineyard

7h 04m1 stop New York John F Kennedy Intl

$343JetBlue

Fri, Aug 28 - Tue, Sep 1

12:28 pm - 7:12 pmACK Nantucket Memorial-ORD Chicago O'Hare Intl

7h 44m1 stop New York LaGuardia

6:00 am - 2:41 pmORD Chicago O'Hare Intl-ACK Nantucket Memorial

7h 41m1 stop New York John F Kennedy Intl

$358Delta

Fri, Aug 28 - Tue, Sep 1

4:40 pm - 10:24 pmACK Nantucket Memorial-ORD Chicago O'Hare Intl

6h 44m1 stop New York LaGuardia

6:59 am - 3:57 pmORD Chicago O'Hare Intl-ACK Nantucket Memorial

7h 58m2 stops Detroit Metropolitan Wayne County New York LaGuardia

$364Delta

Fri, Aug 28 - Tue, Sep 1

12:28 pm - 11:57 pmACK Nantucket Memorial-ORD Chicago O'Hare Intl

12h 29m2 stops New York LaGuardia Atlanta Hartsfield-Jackson

6:59 am - 3:57 pmORD Chicago O'Hare Intl-ACK Nantucket Memorial

7h 58m2 stops Detroit Metropolitan Wayne County New York LaGuardia

$369Delta

Wed, Sep 2 - Sun, Sep 6

4:15 pm - 11:22 pmACK Nantucket Memorial-ORD Chicago O'Hare Intl

8h 07m1 stop Newark

11:59 am - 3:49 pmORD Chicago O'Hare Intl-ACK Nantucket Memorial

2h 50mnonstop

$378United Airlines

Wed, Sep 2 - Tue, Sep 8

4:20 pm - 9:58 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

6h 38m1 stop New York John F Kennedy Intl

9:35 am - 3:13 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

4h 38m1 stop New York John F Kennedy Intl

$382JetBlue

Wed, Sep 2 - Sun, Sep 6

4:15 pm - 10:15 pmACK Nantucket Memorial-ORD Chicago O'Hare Intl

7h 00m1 stop Newark

7:05 am - 3:03 pmORD Chicago O'Hare Intl-ACK Nantucket Memorial

6h 58m1 stop Newark

$388United Airlines

Wed, Sep 2 - Sun, Sep 6

12:02 pm - 5:35 pmACK Nantucket Memorial-ORD Chicago O'Hare Intl

6h 33m1 stop New York John F Kennedy Intl

6:00 am - 3:24 pmORD Chicago O'Hare Intl-ACK Nantucket Memorial

8h 24m1 stop New York John F Kennedy Intl

$399JetBlue

Recent last minute flight deals from Cape Cod and the Islands to Chicago

Sat, Aug 15 - Sat, Aug 22

10:49 am - 5:14 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

7h 25m1 stop Washington, D.C. Reagan-National

11:15 am - 2:57 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

2h 42mnonstop

$406American Airlines

Sat, Aug 15 - Wed, Aug 19

5:03 pm - 9:41 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

5h 38m1 stop Washington, D.C. Reagan-National

10:53 am - 5:29 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

5h 36m1 stop Washington, D.C. Reagan-National

$415American Airlines

Sat, Aug 15 - Sat, Aug 22

5:03 pm - 9:41 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

5h 38m1 stop Washington, D.C. Reagan-National

9:57 am - 4:32 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

5h 35m1 stop Washington, D.C. Reagan-National

$415American Airlines

Sat, Aug 15 - Wed, Aug 19

3:27 pm - 5:47 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

3h 20mnonstop

8:00 am - 1:14 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

4h 14m1 stop New York LaGuardia

$702American Airlines

Sat, Aug 15 - Sat, Aug 22

3:27 pm - 5:47 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

3h 20mnonstop

11:15 am - 2:57 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

2h 42mnonstop

$757American Airlines

Sat, Aug 15 - Wed, Aug 19

11:02 am - 10:29 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

12h 27m1 stop Boston Logan Intl

7:05 am - 5:30 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

9h 25m2 stops Newark Nantucket Memorial

$811Multiple Airlines

Sat, Aug 15 - Wed, Aug 19

11:02 am - 11:22 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

13h 20m2 stops Boston Logan Intl Newark

8:40 am - 5:30 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

7h 50m2 stops Newark Nantucket Memorial

$816Multiple Airlines

Sat, Aug 15 - Sat, Aug 22

11:02 am - 11:22 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

13h 20m2 stops Boston Logan Intl Newark

9:40 pm - 5:25 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

18h 45m1 stop Boston Logan Intl

$834Multiple Airlines

Sat, Aug 15 - Sat, Aug 22

11:02 am - 12:59 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

26h 57m3 stops Boston Logan Intl Newark Cleveland Hopkins Intl

9:40 pm - 7:40 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

21h 00m1 stop Boston Logan Intl

$855Multiple Airlines

Fri, Aug 14 - Sat, Aug 15

4:20 pm - 9:58 pmHYA Hyannis Barnstable-ORD Chicago O'Hare Intl

6h 38m1 stop New York John F Kennedy Intl

9:40 am - 3:13 pmORD Chicago O'Hare Intl-HYA Hyannis Barnstable

4h 33m1 stop New York John F Kennedy Intl

$991JetBlue

Useful Info

Low season	January
High season	July
Cheapest flight	$138

Best time to beat the crowds with an average 12% drop in price.

Most popular time to fly with an average 17% increase in price.

Flight from Nantucket to Chicago

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.

Gurnee

Merrillville

South Haven

Oak Brook

Saint Joseph

Tinley Park

Hammond

Elk Grove Village

Des Plaines

Hoffman Estates

Portage

South Holland

Willowbrook

Oakbrook Terrace

Lansing

Delavan

Alsip

Northbrook

Lisle

Elmhurst

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Chicago (ORD)

ORD

$138 Find Cheap Flights from Cape Cod and the Islands to Chicago - Compare and Save

Cheap Flights from Cape Cod and the Islands to Chicago

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

Recent one-way flight deals from Cape Cod and the Islands to Chicago

Recent last minute flight deals from Cape Cod and the Islands to Chicago

Recent direct flight deals from Cape Cod and the Islands to Chicago

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FAQs for booking Cape Cod and the Islands to Chicago flights

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Everything you need to know for your flight to Chicago

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