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Cheap flights from Chicago to the Cayman Islands from $185

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to the Cayman Islands departing on 1/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago to the Cayman Islands

Cheap round-trip flights

These are some of the best round-trip flight deals from Chicago to the Cayman Islands that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Chicago to the Cayman Islands.

Cheap last minute flights

Planning a quick getaway from Chicago to the Cayman Islands? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to the Cayman Islands, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Chicago to the Cayman Islands

Find recent round-trip train or bus tickets from Chicago to the Cayman Islands.

All round-trip flight deals to the Cayman Islands

The cheapest plane tickets to the Cayman Islands found on KAYAK recently.
7:25 am - 4:10 pmMDW-GCM
7h 45m1 stop
4:45 pm - 8:44 amGCM-MDW
16h 59m1 stop
Wed, Feb 19 - Fri, Feb 28
1:34 pm - 11:40 amORD-GCM
21h 06m1 stop
11:30 am - 12:45 pmGCM-ORD
26h 15m2 stops
Thu, Jan 16 - Tue, Jan 21
5:45 am - 12:55 pmMDW-GCM
6h 10m1 stop
2:10 pm - 11:15 pmGCM-MDW
10h 05m2 stops
$532Southwest
Find Deal
Tue, Feb 25 - Sat, Mar 1
5:45 am - 12:55 pmMDW-GCM
6h 10m1 stop
2:10 pm - 9:45 pmGCM-MDW
8h 35m1 stop
$547Southwest
Find Deal
Tue, Feb 25 - Sat, Mar 1
6:30 pm - 12:35 pmORD-GCM
17h 05m1 stop
1:00 pm - 7:19 pmGCM-ORD
7h 19m1 stop
$588American Airlines
Find Deal
Sat, Feb 1 - Wed, Feb 5
6:00 am - 12:44 pmMDW-GCM
5h 44m1 stop
2:09 pm - 10:20 pmGCM-MDW
9h 11m1 stop
$588Delta
Find Deal
Sun, Feb 23 - Fri, Feb 28
5:00 am - 4:20 pmORD-GCM
10h 20m2 stops
1:40 pm - 9:41 pmGCM-ORD
9h 01m1 stop
$593American Airlines
Find Deal
Wed, Feb 26 - Wed, Mar 5
6:00 am - 12:44 pmMDW-GCM
5h 44m1 stop
2:09 pm - 10:20 pmGCM-MDW
9h 11m1 stop
$613Delta
Find Deal
Fri, Feb 21 - Thu, Feb 27
8:48 am - 12:45 pmORD-GCM
3h 57mnonstop
1:25 pm - 10:00 pmGCM-ORD
8h 35m1 stop
$674United Airlines
Find Deal
Sun, Mar 16 - Fri, Mar 21
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$694United Airlines
Find Deal
Thu, Dec 19 - Thu, Dec 26
1:45 pm - 9:20 pmORD-GCM
30h 35m2 stops
Wed, Jan 22
2:59 pm - 4:10 pmORD-GCM
24h 11m2 stops
Tue, Jan 21
8:25 pm - 1:40 pmORD-GCM
16h 15m1 stop
$240Air Canada
Find Deal
Wed, Nov 27
6:10 pm - 1:40 pmORD-GCM
42h 30m2 stops
$245Air Canada
Find Deal
Tue, Nov 26
5:40 am - 2:32 pmORD-GCM
7h 52m1 stop
$297Delta
Find Deal
Sun, Dec 22
8:50 am - 2:00 pmORD-GCM
4h 10mnonstop
$318American Airlines
Find Deal
Sat, Jan 25
5:00 am - 4:20 pmORD-GCM
10h 20m2 stops
$322American Airlines
Find Deal
Fri, Feb 21
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
$338United Airlines
Find Deal
Thu, Dec 19
5:40 am - 12:27 pmORD-GCM
5h 47m1 stop
$357Delta
Find Deal
Sat, Dec 21
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
$363United Airlines
Find Deal
Fri, Dec 20
6:10 pm - 1:40 pmORD-GCM
42h 30m2 stops
11:30 am - 10:43 pmGCM-ORD
12h 13m2 stops
Tue, Nov 26 - Wed, Dec 25
6:30 pm - 4:10 pmMDW-GCM
20h 40m1 stop
11:30 am - 1:36 pmGCM-MDW
27h 06m1 stop
Tue, Nov 26 - Wed, Dec 25
8:50 am - 4:25 pmORD-GCM
6h 35m1 stop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$723United Airlines
Find Deal
Tue, Nov 26 - Wed, Dec 25
7:35 am - 4:25 pmORD-GCM
7h 50m1 stop
2:25 pm - 11:00 pmGCM-ORD
9h 35m1 stop
$733United Airlines
Find Deal
Tue, Nov 26 - Wed, Dec 25
5:00 am - 2:15 pmORD-GCM
8h 15m2 stops
1:35 pm - 7:30 pmGCM-ORD
6h 55m1 stop
$778American Airlines
Find Deal
Tue, Nov 26 - Wed, Dec 25
1:09 pm - 1:40 pmORD-GCM
47h 31m3 stops
11:30 am - 10:43 pmGCM-ORD
12h 13m2 stops
Tue, Nov 26 - Wed, Dec 25
7:59 pm - 4:10 pmORD-GCM
19h 11m1 stop
4:45 pm - 7:07 pmGCM-ORD
27h 22m1 stop
Tue, Nov 26 - Mon, Dec 2
8:25 pm - 12:35 pmORD-GCM
15h 10m1 stop
1:36 pm - 9:38 pmGCM-ORD
9h 02m1 stop
$968American Airlines
Find Deal
Sat, Nov 23 - Tue, Dec 3
2:17 pm - 1:49 pmMDW-GCM
46h 32m2 stops
2:50 pm - 1:35 pmGCM-MDW
23h 45m2 stops
$3,312WestJet
Find Deal
Tue, Nov 26 - Mon, Dec 2
5:00 pm - 4:55 pmORD-GCM
22h 55m2 stops
6:50 pm - 6:45 pmGCM-ORD
24h 55m2 stops
$8,153British Airways
Find Deal
Fri, Nov 22 - Sat, Nov 30
8:48 am - 12:45 pmORD-GCM
3h 57mnonstop
1:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$574United Airlines
Find Deal
Tue, Mar 18 - Tue, Mar 25
8:50 am - 2:00 pmORD-GCM
4h 10mnonstop
3:00 pm - 6:10 pmGCM-ORD
4h 10mnonstop
$624American Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$642United Airlines
Find Deal
Mon, Dec 23 - Wed, Jan 1
9:00 am - 1:55 pmORD-GCM
3h 55mnonstop
2:55 pm - 6:05 pmGCM-ORD
4h 10mnonstop
$649American Airlines
Find Deal
Sat, Feb 15 - Sat, Mar 1
8:39 am - 1:35 pmORD-GCM
3h 56mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$689United Airlines
Find Deal
Sat, Mar 1 - Fri, Mar 7
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$694United Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
8:39 am - 1:35 pmORD-GCM
3h 56mnonstop
2:40 pm - 5:56 pmGCM-ORD
4h 16mnonstop
$714United Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$719United Airlines
Find Deal
Sun, Dec 22 - Sun, Dec 29
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$769United Airlines
Find Deal
Wed, Dec 25 - Wed, Jan 1
8:39 am - 1:35 pmORD-GCM
3h 56mnonstop
2:40 pm - 5:56 pmGCM-ORD
4h 16mnonstop
$838United Airlines
Find Deal
Sat, Jan 4 - Sat, Jan 11

Southwest flights from Chicago to Cayman Islands

Our best Southwest deals on Chicago to Cayman Islands flight tickets
Southwest
Feb 25
MDW5:45 amChicago Midway
6h 10m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Mar 1
GCM2:10 pmGeorge Town Owen Roberts Intl
10h 05m
2 stops
MDW11:15 pmChicago Midway
Southwest
Feb 25
MDW5:45 amChicago Midway
6h 10m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Mar 1
GCM2:10 pmGeorge Town Owen Roberts Intl
8h 35m
1 stop
MDW9:45 pmChicago Midway
Southwest
Jan 1
MDW6:00 amChicago Midway
5h 55m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 8
GCM1:50 pmGeorge Town Owen Roberts Intl
20h 30m
2 stops
MDW9:20 amChicago Midway

Delta flights from Chicago to Cayman Islands

Our best Delta deals on Chicago to Cayman Islands flight tickets
Delta
Feb 23
MDW6:00 amChicago Midway
5h 44m
1 stop
GCM12:44 pmGeorge Town Owen Roberts Intl
Feb 28
GCM2:09 pmGeorge Town Owen Roberts Intl
9h 11m
1 stop
MDW10:20 pmChicago Midway
Delta
Feb 21
MDW6:00 amChicago Midway
5h 44m
1 stop
GCM12:44 pmGeorge Town Owen Roberts Intl
Feb 27
GCM2:09 pmGeorge Town Owen Roberts Intl
9h 11m
1 stop
MDW10:20 pmChicago Midway
Delta
Dec 24
ORD7:05 amChicago O'Hare Intl
6h 27m
1 stop
GCM2:32 pmGeorge Town Owen Roberts Intl
Dec 31
GCM3:47 pmGeorge Town Owen Roberts Intl
9h 09m
1 stop
ORD11:56 pmChicago O'Hare Intl

See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Chicago to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest day to depart on your flight to Cayman Islands?

Our data shows that Tuesday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $576. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Cayman Islands on Friday is $675.

What is the cheapest Chicago to Cayman Islands flight route?

Fly from Chicago O'Hare Intl to George Town Owen Roberts Intl for the best Chicago - Cayman Islands flight prices

What cabin class options are available on Chicago to Cayman Islands flights?

There are 2 cabin classes available to choose from on Chicago to Cayman Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Chicago to Cayman Islands flights?

You could potentially save up to 43% on your flight if you consider stops on a Chicago to Cayman Islands flight.

Cheap Chicago to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Cayman Islands

Best Price Found

$185

Fastest flight time

3h 47m

Direct flights

Every day

Airports in Cayman Islands

1 airport
The best one-way flight to Cayman Islands from Chicago in the past 72 hours is $185. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $488.
The fastest flight from Chicago to Cayman Islands takes 3h 47m
Direct flights go from Chicago to Cayman Islands every day.
There is 1 airport near Cayman Islands: George Town Owen Roberts Intl (GCM)

  • When did momondo last update prices for flights from Chicago to Cayman Islands?

    Prices for flights from Chicago to Cayman Islands refresh daily.

  • How many operators does momondo search for flights from Chicago to Cayman Islands?

  • How old do you have to be to fly from Chicago to Cayman Islands?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The travel and health documents you'll need for your trip to Cayman Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Chicago to Cayman Islands?


Best airlines flying from Chicago to Cayman Islands

Compare and see reviews for airlines that fly from Chicago to Cayman Islands with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $348Free CancellationRating
8.0
8,755 reviews
Search Delta flights
American AirlinesPriceFrom $368Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $420Free CancellationRating
7.4
9,172 reviews
Search United Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cayman Islands?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Cayman Islands. momondo saves you time and could save you money on your trip.

Can I find flights from Chicago to Cayman Islands with flexible booking policies on momondo?

Yes. All flights to Cayman Islands from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from Chicago to Cayman Islands?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Cayman Islands from Chicago.

I’m not ready to book a flight from Chicago to Cayman Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Cayman Islands from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.


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