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>

$280 CHEAP FLIGHTS from Grand Cayman to Chicago

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

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Flights Deals

Cheap Flight Deals 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.

Round-trip

One-way

Recent round-trip flight deals from Grand Cayman to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Grand Cayman to Chicago.

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

8:50 am - 5:41 pmGCM-ORD

8h 51m1 stop

5:51 am - 11:40 amORD-GCM

29h 49m2 stops

$493

Find Deal

Sat, May 31 - Sat, Jun 7

8:50 am - 5:41 pmGCM-ORD

8h 51m1 stop

9:55 am - 11:40 amORD-GCM

25h 45m1 stop

$501

Find Deal

Sat, May 31 - Sat, Jun 7

8:50 am - 5:41 pmGCM-ORD

8h 51m1 stop

4:35 pm - 9:20 pmORD-GCM

28h 45m3 stops

$547

Find Deal

Sat, May 31 - Sat, Jun 7

8:50 am - 7:09 pmGCM-ORD

34h 19m3 stops

5:51 am - 11:40 amORD-GCM

29h 49m2 stops

$598

Find Deal

Sat, May 31 - Sat, Jun 7

8:50 am - 7:09 pmGCM-ORD

34h 19m3 stops

4:35 pm - 9:20 pmORD-GCM

28h 45m3 stops

$648

Find Deal

Sat, May 31 - Sat, Jun 7

1:45 pm - 6:07 pmGCM-ORD

4h 22mnonstop

9:26 am - 1:30 pmORD-GCM

4h 04mnonstop

$736United Airlines

Find Deal

Sat, May 31 - Sat, Jun 7

12:25 pm - 11:56 pmGCM-ORD

11h 31m2 stops

5:00 am - 1:10 pmORD-GCM

8h 10m2 stops

$1,187American Airlines

Find Deal

Fri, May 16 - Tue, May 20

Useful Info

Low season	September
High season	November
Cheapest flight	$280

Best time to beat the crowds with an average 41% drop in price.

Most popular time to fly with an average 12% 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 $294

Business Class flights to Chicagofrom $290

Prem Econ Class flights to Chicagofrom $213

Economy Class flights to Chicagofrom $24

$280 Find Cheap Flights from Grand Cayman to Chicago

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

Cheap Flight Deals 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

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