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>

$264 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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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

Recent round-trip flight deals from Grand Cayman to Chicago

Fri, Nov 14 - Sun, Nov 16

1:30 pm - 9:50 pmGCM-ORD

9h 20m1 stop

6:05 am - 12:35 pmORD-GCM

5h 30m1 stop

$410Southwest

Find Deal

Thu, Oct 16 - Sun, Oct 19

12:50 pm - 9:51 amGCM-ORD

21h 01m2 stops

3:35 pm - 11:55 amORD-GCM

20h 20m2 stops

$450Air Canada

Find Deal

Mon, Sep 15 - Mon, Sep 22

4:45 pm - 9:18 amGCM-ORD

16h 33m1 stop

10:27 am - 9:20 pmORD-GCM

10h 53m1 stop

$474

Find Deal

Fri, Nov 14 - Sun, Nov 16

1:30 pm - 9:50 pmGCM-ORD

9h 20m1 stop

4:25 pm - 12:35 pmORD-GCM

19h 10m2 stops

$476Southwest

Find Deal

Wed, Sep 3 - Sat, Sep 6

11:30 am - 9:18 amGCM-ORD

21h 48m1 stop

10:27 am - 11:40 amORD-GCM

25h 13m1 stop

$485

Find Deal

Fri, Nov 14 - Sun, Nov 16

2:02 pm - 9:44 pmGCM-MDW

8h 42m1 stop

6:00 am - 12:37 pmMDW-GCM

5h 37m1 stop

$511Delta

Find Deal

Wed, Sep 3 - Sat, Sep 6

12:10 pm - 7:42 amGCM-ORD

19h 32m2 stops

8:29 pm - 11:10 amORD-GCM

14h 41m2 stops

$624American Airlines

Find Deal

Mon, Sep 15 - Mon, Sep 22

12:52 pm - 9:36 pmGCM-MDW

8h 44m1 stop

6:00 am - 11:36 amMDW-GCM

5h 36m1 stop

$626Delta

Find Deal

Thu, Aug 14 - Sun, Aug 17

2:10 pm - 11:59 pmGCM-ORD

9h 49m2 stops

5:20 am - 1:12 pmORD-GCM

7h 52m2 stops

$879American Airlines

Find Deal

Sat, Aug 16 - Mon, Aug 18

1:45 pm - 6:07 pmGCM-ORD

4h 22mnonstop

6:00 am - 12:30 pmORD-GCM

6h 30m1 stop

$899United Airlines

Find Deal

Useful Info

Cheapest flight	$264

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 $283

Business Class flights to Chicagofrom $369

Prem Econ Class flights to Chicagofrom $99

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.

$264 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

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