How does KAYAK find such low prices on flights from Grand Cayman 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 Grand Cayman to Chicago. Visit our flight page for the latest deals!>/a>

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Grand Cayman to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Grand Cayman is likely to change within 7 days, so travelers know whether to wait or book now. Visit our flight page for the latest deals!>/a>

What is the Hacker Fare option on flights from Grand Cayman 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 Grand Cayman with another airline. Visit our flight page for the latest deals!>/a>

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Grand Cayman 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 Grand Cayman up to 3 days before/after your preferred dates. You can then pick the flights that suit you best. Visit our flight page for the latest deals!>/a>

$286 CHEAP FLIGHTS from Grand Cayman to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

...and more

Travelers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals

Cheap Flights from Grand Cayman to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Grand Cayman 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.

Round-trip

One-way

Last minute

Recent round-trip flight deals from Grand Cayman to Chicago

Fri, Aug 1 - Fri, Aug 8

7:00 am - 4:11 pmGCM-ORD

9h 11m1 stop

8:09 am - 9:20 pmORD-GCM

13h 11m1 stop

$597

Find Deal

Sat, Jul 19 - Sat, Jul 19

8:50 am - 4:11 pmGCM-ORD

7h 21m1 stop

9:10 pm - 11:40 amORD-GCM

38h 30m2 stops

$607

Find Deal

Fri, Aug 1 - Fri, Aug 8

7:00 am - 4:11 pmGCM-ORD

9h 11m1 stop

8:09 am - 2:50 pmORD-GCM

30h 41m2 stops

$619

Find Deal

Fri, Aug 1 - Fri, Aug 8

7:00 am - 4:11 pmGCM-ORD

9h 11m1 stop

6:17 pm - 2:50 pmORD-GCM

20h 33m3 stops

$627

Find Deal

Fri, Aug 1 - Fri, Aug 8

7:00 am - 8:55 amGCM-ORD

25h 55m3 stops

6:17 pm - 2:50 pmORD-GCM

20h 33m3 stops

$662

Find Deal

Fri, Aug 1 - Fri, Aug 8

7:00 am - 7:50 amGCM-ORD

24h 50m2 stops

6:17 pm - 2:50 pmORD-GCM

20h 33m3 stops

$679

Find Deal

Sat, Jul 19 - Sat, Jul 19

1:45 pm - 6:07 pmGCM-ORD

4h 22mnonstop

9:16 pm - 12:30 pmORD-GCM

39h 14m2 stops

$953United Airlines

Find Deal

Sat, Jul 19 - Sat, Jul 19

1:45 pm - 6:07 pmGCM-ORD

4h 22mnonstop

9:07 pm - 12:30 pmORD-GCM

15h 23m1 stop

$1,095United Airlines

Find Deal

Sat, Jul 19 - Sat, Jul 19

8:50 am - 4:11 pmGCM-ORD

7h 21m1 stop

7:49 pm - 9:20 pmORD-GCM

25h 31m3 stops

$1,634

Find Deal

Useful Info

Low season	September
High season	November
Cheapest flight	$286

Best time to beat the crowds with an average 39% drop in price.

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

Flight from George Town to Chicago

How does KAYAK find such low prices on flights from Grand Cayman 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 Grand Cayman to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Grand Cayman to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Grand Cayman 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 Grand Cayman 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 Grand Cayman with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Grand Cayman 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 Grand Cayman 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

Cabin class

Complete your trip

Direct Flights

Flights to other cities

Origins

Other airports

Return flight deals

Cabin class types available on flights to Grand Cayman

First Class flights to Chicagofrom $299

Business Class flights to Chicagofrom $326

Prem Econ Class flights to Chicagofrom $213

Economy Class flights to Chicagofrom $24

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.

$286 Find Cheap Flights from Grand Cayman to Chicago

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

Cheap Flights from Grand Cayman to Chicago

Recent round-trip flight deals from Grand Cayman to Chicago

Recent one-way flight deals from Grand Cayman to Chicago

Recent last minute flight deals from Grand Cayman to Chicago

Good to know

FAQs for booking flights from Grand Cayman to Chicago

How does KAYAK find such low prices on flights from Grand Cayman 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 Grand Cayman to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Grand Cayman to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Grand Cayman 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 Grand Cayman 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 Grand Cayman with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Grand Cayman 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 Grand Cayman 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

Cabin class types available on flights to Grand Cayman

Complete your trip to Chicago with a hotel stay or car rental

Find direct flights for Chicago

Flights to other popular destinations

Flights from domestic origins to Grand Cayman

Choose which airport to fly into in Chicago

Find deals for your return flight