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Cheap flights from Chicago to the Cayman Islands from $179

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 2/4. 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.
8:02 pm - 4:10 pmORD-GCM
19h 08m1 stop
11:30 am - 11:51 pmGCM-ORD
13h 21m2 stops
Tue, Dec 3 - Thu, Dec 5
7:25 am - 9:20 pmORD-GCM
36h 55m2 stops
11:30 am - 7:07 pmGCM-ORD
8h 37m1 stop
Thu, Dec 5 - Tue, Dec 10
5:45 am - 12:55 pmORD-GCM
6h 10m1 stop
1:50 pm - 10:20 pmGCM-ORD
9h 30m2 stops
$545Southwest
Find Deal
Thu, Jan 2 - Wed, Jan 8
6:30 pm - 12:35 pmORD-GCM
17h 05m1 stop
1:40 pm - 9:42 pmGCM-ORD
9h 02m1 stop
$578American Airlines
Find Deal
Sat, Jan 25 - Wed, Jan 29
6:00 am - 12:27 pmMDW-GCM
5h 27m1 stop
3:47 pm - 10:06 pmGCM-MDW
7h 19m1 stop
$578Delta
Find Deal
Tue, Dec 24 - Tue, Dec 31
5:40 am - 12:55 pmMDW-GCM
6h 15m1 stop
1:50 pm - 9:35 pmGCM-MDW
8h 45m2 stops
$579Southwest
Find Deal
Sun, Jan 12 - Fri, Jan 17
5:02 am - 2:30 pmORD-GCM
8h 28m2 stops
1:00 pm - 10:04 pmGCM-ORD
10h 04m2 stops
$583American Airlines
Find Deal
Tue, Dec 31 - Tue, Jan 7
6:00 am - 12:29 pmMDW-GCM
5h 29m1 stop
1:55 pm - 9:49 pmGCM-MDW
8h 54m1 stop
$603Delta
Find Deal
Fri, Feb 21 - Fri, Feb 28
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$604United Airlines
Find Deal
Fri, Dec 20 - Thu, Dec 26
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$606United Airlines
Find Deal
Wed, Dec 25 - Sun, Dec 29
4:25 pm - 4:10 pmORD-GCM
22h 45m1 stop
Tue, Feb 4
8:02 pm - 4:10 pmORD-GCM
19h 08m1 stop
Tue, Dec 3
5:45 am - 12:55 pmORD-GCM
6h 10m1 stop
$211Southwest
Find Deal
Sun, Jan 5
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
$288United Airlines
Find Deal
Wed, Dec 25
5:45 am - 2:32 pmORD-GCM
7h 47m1 stop
$292Delta
Find Deal
Wed, Dec 25
6:00 am - 12:27 pmMDW-GCM
5h 27m1 stop
$292Delta
Find Deal
Wed, Dec 25
8:30 pm - 10:56 amORD-GCM
14h 26m2 stops
$298American Airlines
Find Deal
Sun, May 4
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
$333United Airlines
Find Deal
Thu, Jan 2
8:10 pm - 12:55 pmMDW-GCM
15h 45m2 stops
$451Southwest
Find Deal
Sat, Dec 28
8:50 am - 1:45 pmORD-GCM
3h 55mnonstop
$738American Airlines
Find Deal
Sat, Dec 28
8:11 pm - 2:50 pmORD-GCM
17h 39m2 stops
4:00 pm - 7:32 pmGCM-ORD
28h 32m1 stop
Fri, Nov 8 - Sun, Nov 10
8:11 pm - 2:50 pmORD-GCM
17h 39m2 stops
2:50 pm - 6:41 pmGCM-ORD
28h 51m3 stops
Fri, Nov 8 - Mon, Nov 11
8:11 pm - 2:50 pmORD-GCM
17h 39m2 stops
2:50 pm - 1:44 pmGCM-ORD
23h 54m2 stops
Fri, Nov 8 - Mon, Nov 11
9:41 pm - 4:10 pmMDW-GCM
17h 29m2 stops
2:50 pm - 10:20 amGCM-MDW
20h 30m1 stop
Fri, Nov 8 - Mon, Nov 11
9:41 pm - 4:10 pmMDW-GCM
17h 29m2 stops
11:30 am - 6:47 amGCM-MDW
20h 17m1 stop
Fri, Nov 8 - Sun, Nov 10
8:25 pm - 3:00 pmORD-GCM
17h 35m1 stop
6:50 pm - 7:32 pmGCM-ORD
25h 42m2 stops
Sat, Nov 9 - Wed, Nov 13
8:25 pm - 12:30 pmORD-GCM
15h 05m1 stop
1:00 pm - 7:33 pmGCM-ORD
7h 33m1 stop
$958American Airlines
Find Deal
Fri, Nov 8 - Sun, Nov 10
8:39 am - 1:35 pmORD-GCM
3h 56mnonstop
5:35 pm - 7:42 amGCM-ORD
15h 07m1 stop
$979United Airlines
Find Deal
Sat, Nov 9 - Wed, Nov 13
8:50 am - 4:35 pmORD-GCM
6h 45m1 stop
5:35 pm - 11:59 pmGCM-ORD
7h 24m1 stop
$983United Airlines
Find Deal
Sat, Nov 9 - Wed, Nov 13
7:10 pm - 1:49 pmMDW-GCM
41h 39m2 stops
2:50 pm - 5:54 pmGCM-MDW
28h 04m2 stops
$3,348WestJet
Find Deal
Fri, Nov 8 - Mon, Nov 11
8:48 am - 12:45 pmORD-GCM
3h 57mnonstop
1:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$571United Airlines
Find Deal
Wed, Mar 19 - Thu, Mar 27
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$572United Airlines
Find Deal
Wed, Dec 25 - Tue, Dec 31
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$604United Airlines
Find Deal
Fri, Dec 20 - Thu, Dec 26
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$606United Airlines
Find Deal
Wed, Dec 25 - Sun, Dec 29
8:50 am - 2:00 pmORD-GCM
4h 10mnonstop
3:00 pm - 6:10 pmGCM-ORD
4h 10mnonstop
$614American Airlines
Find Deal
Sat, Feb 1 - Sat, Feb 8
9:00 am - 1:55 pmORD-GCM
3h 55mnonstop
3:39 pm - 6:50 pmGCM-ORD
4h 11mnonstop
$639American Airlines
Find Deal
Sat, Mar 1 - Sat, Mar 8
8:39 am - 1:35 pmORD-GCM
3h 56mnonstop
2:40 pm - 5:56 pmGCM-ORD
4h 16mnonstop
$644United Airlines
Find Deal
Sat, Dec 7 - Sat, Dec 14
8:48 am - 12:45 pmORD-GCM
3h 57mnonstop
1:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$654United Airlines
Find Deal
Mon, Mar 24 - Wed, Mar 26
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$664United Airlines
Find Deal
Tue, Dec 24 - Tue, Dec 31
8:48 am - 1:45 pmORD-GCM
3h 57mnonstop
2:50 pm - 6:06 pmGCM-ORD
4h 16mnonstop
$669United Airlines
Find Deal
Tue, Dec 24 - Mon, Dec 30

Southwest flights from Chicago to Cayman Islands

Our best Southwest deals on Chicago to Cayman Islands flight tickets
Southwest
Jan 2
ORD5:45 amChicago O'Hare Intl
6h 10m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 8
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 30m
2 stops
ORD10:20 pmChicago O'Hare Intl
Southwest
Jan 12
MDW5:40 amChicago Midway
6h 15m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 17
GCM1:50 pmGeorge Town Owen Roberts Intl
8h 45m
2 stops
MDW9:35 pmChicago Midway
Southwest
Dec 24
MDW6:00 amChicago Midway
5h 55m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Dec 29
GCM1:50 pmGeorge Town Owen Roberts Intl
11h 30m
2 stops
MDW12:20 amChicago Midway

Air Canada flights from Chicago to Cayman Islands

Our best Air Canada deals on Chicago to Cayman Islands flight tickets
Air Canada
Jan 25
ORD8:30 pmChicago O'Hare Intl
17h 30m
1 stop
GCM3:00 pmGeorge Town Owen Roberts Intl
Jan 31
GCM2:40 pmGeorge Town Owen Roberts Intl
21h 14m
2 stops
ORD10:54 amChicago O'Hare Intl
Air Canada
Jan 22
ORD2:05 pmChicago O'Hare Intl
22h 35m
1 stop
GCM1:40 pmGeorge Town Owen Roberts Intl
Jan 30
GCM2:40 pmGeorge Town Owen Roberts Intl
21h 14m
2 stops
ORD10:54 amChicago O'Hare Intl
Air Canada
Dec 4
ORD8:25 pmChicago O'Hare Intl
16h 15m
1 stop
GCM1:40 pmGeorge Town Owen Roberts Intl
Dec 12
GCM2:40 pmGeorge Town Owen Roberts Intl
21h 14m
2 stops
ORD10:54 amChicago O'Hare Intl

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 airline that flies to Cayman Islands from Chicago?

Delta. Delta, American Airlines, and United Airlines are the most popular carriers operating from Chicago to Cayman Islands

What is the cheapest Chicago to Cayman Islands flight route?

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

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

You could potentially save up to 37% 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

$179

Fastest flight time

3h 55m

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 $179. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $477.
The fastest flight from Chicago to Cayman Islands takes 3h 55m
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 $351Free CancellationRating
8.0
8,830 reviews
Search Delta flights
American AirlinesPriceFrom $368Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $405Free CancellationRating
7.4
9,215 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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