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Cheap flights from Chicago to the Cayman Islands from $168

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 4/29. 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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0 bags

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Find the cheapest flights from Chicago to the Cayman Islands

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Chicago to the Cayman Islands.
7:00 pm - 4:10 pmORD-GCM
21h 10m1 stop
8:50 am - 5:41 pmGCM-ORD
8h 51m1 stop
Tue, May 6 - Sat, May 10
3:11 pm - 11:40 amORD-GCM
20h 29m1 stop
8:50 am - 10:47 pmGCM-ORD
13h 57m1 stop
Sat, Sep 13 - Sat, Sep 20
5:50 am - 11:50 amMDW-GCM
6h 00m1 stop
12:45 pm - 8:15 pmGCM-MDW
7h 30m1 stop
$552Southwest
Find Deal
Fri, May 16 - Wed, May 21
4:15 pm - 11:50 amMDW-GCM
19h 35m2 stops
12:45 pm - 10:05 pmGCM-MDW
9h 20m1 stop
$566Southwest
Find Deal
Thu, May 15 - Tue, May 20
5:00 am - 1:10 pmORD-GCM
8h 10m1 stop
12:10 pm - 11:56 pmGCM-ORD
11h 46m1 stop
$596American Airlines
Find Deal
Wed, May 14 - Wed, May 21
5:00 am - 1:10 pmORD-GCM
8h 10m2 stops
12:25 pm - 9:43 pmGCM-ORD
9h 18m1 stop
$600American Airlines
Find Deal
Wed, May 14 - Wed, May 21
5:30 am - 11:20 amORD-GCM
5h 50m1 stop
12:35 pm - 9:20 pmGCM-ORD
8h 45m1 stop
$610Delta
Find Deal
Wed, May 14 - Wed, May 21
6:00 am - 11:20 amMDW-GCM
5h 20m1 stop
12:35 pm - 9:27 pmGCM-MDW
8h 52m1 stop
$610Delta
Find Deal
Wed, May 14 - Wed, May 21
8:10 pm - 12:30 pmORD-GCM
16h 20m1 stop
1:45 pm - 6:07 pmGCM-ORD
4h 22mnonstop
$625United Airlines
Find Deal
Mon, Jun 9 - Sat, Jun 14
9:26 am - 1:30 pmORD-GCM
4h 04mnonstop
1:35 pm - 11:12 pmGCM-ORD
9h 37m1 stop
$630United Airlines
Find Deal
Sat, May 17 - Fri, May 23

Delta flights from Chicago to Cayman Islands

Our best Delta deals on Chicago to Cayman Islands flight tickets
Delta
May 14
ORD5:30 amChicago O'Hare Intl
5h 50m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl
May 21
GCM12:35 pmGeorge Town Owen Roberts Intl
8h 45m
1 stop
ORD9:20 pmChicago O'Hare Intl
Delta
May 15
MDW6:00 amChicago Midway
5h 20m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl
May 22
GCM12:35 pmGeorge Town Owen Roberts Intl
8h 52m
1 stop
MDW9:27 pmChicago Midway
Delta
May 29
MDW6:00 amChicago Midway
5h 20m
1 stop
GCM11:20 amGeorge Town Owen Roberts Intl
Jun 5
GCM12:35 pmGeorge Town Owen Roberts Intl
8h 52m
1 stop
MDW9:27 pmChicago Midway

Southwest flights from Chicago to Cayman Islands

Our best Southwest deals on Chicago to Cayman Islands flight tickets
Southwest
May 16
MDW5:50 amChicago Midway
6h 00m
1 stop
GCM11:50 amGeorge Town Owen Roberts Intl
May 21
GCM12:45 pmGeorge Town Owen Roberts Intl
7h 30m
1 stop
MDW8:15 pmChicago Midway
Southwest
May 15
MDW4:15 pmChicago Midway
19h 35m
2 stops
GCM11:50 amGeorge Town Owen Roberts Intl
May 20
GCM12:45 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
MDW10:05 pmChicago Midway
Southwest
May 15
MDW5:50 amChicago Midway
6h 00m
1 stop
GCM11:50 amGeorge Town Owen Roberts Intl
May 20
GCM12:45 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
MDW10:05 pmChicago Midway

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 month to fly to Cayman Islands?

If you aren’t able to travel to Cayman Islands during the month of September, then flying in November is also cheap. Prices for this month can be found on momondo for an average of $601.

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

Our data shows that Sunday is the least expensive day to fly to Cayman Islands. Tickets to fly out on this day can be as low as $688. 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 $1,039.

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

According to our data, the cheapest time of day to fly to Cayman Islands is in the afternoon. momondo users have found flights departing from Chicago to Cayman Islands in the afternoon for as low as $507. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. If you have a flexible travel schedule, then try to avoid flying in the morning when prices are $712 on average. Flights to Cayman Islands from Chicago in the morning are generally more expensive because this time of day is more convenient for travelers’ schedules.

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

How far in advance should I book a flight to Cayman Islands?

You are more likely to see cheaper flights to Cayman Islands from Chicago when booking 23 weeks ahead of your departure date. In general, you can expect to find flights to Cayman Islands for around $673 when searching 23 weeks out.However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Cayman Islands from Chicago for as low as $623 on momondo.

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

There are 3 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.

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

$168

Fastest flight time

3h 55m

Direct flights

Mon and Sun

Airports in Cayman Islands

1 airport
The best one-way flight to Cayman Islands from Chicago in the past 72 hours is $168. The best round-trip flight deal from Chicago to Cayman Islands found on momondo in the last 72 hours is $462.
The fastest flight from Chicago to Cayman Islands takes 3h 55m
Direct flights go from Chicago to Cayman Islands on Monday and Sunday. The only airline offering direct flights is United Airlines.
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 $463Free CancellationRating
8.0
7,899 reviews
Search Delta flights
American AirlinesPriceFrom $468Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $504Free CancellationRating
7.4
8,614 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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Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo