$102 Find Cheap Flights from Chicago O'Hare Airport to Cayman Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from O'Hare Intl to the Cayman Islands departing on 4/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from O'Hare Intl to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town3 stops$449
Cayman Brac
Cayman Brac2 stops$851
George Town
George Town3 stops$449
Cayman Brac
Cayman Brac2 stops$851

Book Cheap O'Hare Intl to the Cayman Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from O'Hare Intl to the Cayman Islands 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.

Recent round-trip flight deals from O'Hare Intl to the Cayman Islands

Sat, Apr 4 - Thu, Apr 9
Spirit Airlines Logo
12:45 pm - 12:57 pm
ORD
-
GCM
24h 12m
3 stops
Spirit Airlines Logo
1:52 pm - 11:17 pm
GCM
-
ORD
9h 25m
1 stop
$449Spirit Airlines
Thu, Apr 9 - Tue, Apr 14
Multiple Airlines Logo
1:55 pm - 10:10 am
ORD
-
GCM
20h 15m
2 stops
Multiple Airlines Logo
3:05 pm - 7:41 am
GCM
-
ORD
16h 36m
1 stop
$457Multiple Airlines
Sat, Apr 11 - Mon, May 25
Multiple Airlines Logo
5:05 am - 12:20 pm
ORD
-
GCM
7h 15m
1 stop
Multiple Airlines Logo
4:45 pm - 7:55 am
GCM
-
ORD
39h 10m
2 stops
$459Multiple Airlines
Tue, Apr 28 - Mon, May 4
Multiple Airlines Logo
2:09 pm - 6:00 pm
ORD
-
GCM
27h 51m
1 stop
Multiple Airlines Logo
4:45 pm - 7:55 am
GCM
-
ORD
39h 10m
2 stops
$464Multiple Airlines
Sat, Apr 4 - Thu, Apr 9
Air Canada Logo
1:55 pm - 10:55 am
ORD
-
GCM
21h 00m
2 stops
Air Canada Logo
11:55 am - 7:25 pm
GCM
-
ORD
7h 30m
1 stop
$466Air Canada
Wed, Apr 8 - Wed, May 27
Multiple Airlines Logo
6:10 pm - 12:57 pm
ORD
-
GCM
18h 47m
1 stop
Multiple Airlines Logo
11:30 am - 7:55 am
GCM
-
ORD
20h 25m
2 stops
$471Multiple Airlines
Sat, May 2 - Sat, May 9
Multiple Airlines Logo
6:40 am - 2:50 pm
ORD
-
GCM
8h 10m
2 stops
Multiple Airlines Logo
8:50 am - 9:37 am
GCM
-
ORD
24h 47m
1 stop
$472Multiple Airlines
Thu, Apr 9 - Tue, Apr 14
Multiple Airlines Logo
1:55 pm - 10:10 am
ORD
-
GCM
20h 15m
2 stops
Multiple Airlines Logo
3:05 pm - 9:39 pm
GCM
-
ORD
30h 34m
2 stops
$473Multiple Airlines
Thu, Mar 26 - Sun, Apr 5
Multiple Airlines Logo
5:05 am - 12:57 pm
ORD
-
GCM
7h 52m
1 stop
Multiple Airlines Logo
1:52 pm - 12:39 pm
GCM
-
ORD
46h 47m
2 stops
$474Multiple Airlines
Tue, Apr 7 - Sun, May 31
Multiple Airlines Logo
4:51 pm - 4:05 pm
ORD
-
GCM
23h 14m
1 stop
Multiple Airlines Logo
4:45 pm - 1:05 pm
GCM
-
ORD
20h 20m
1 stop
$477Multiple Airlines
Booking Insights

KAYAK's insights & trends for O'Hare Intl to the Cayman Islands flights

Get data-powered insights and trends into flights from O'Hare Intl to the Cayman Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Chicago O'Hare Intl Airport to the Cayman Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to the Cayman Islands from Chicago O'Hare Intl Airport found in the last 72 hours was to George Town, at $485 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $485.

What is the cheapest time of day to fly to the Cayman Islands?

The average price for all round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $626 on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $626.

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to the Cayman Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $580, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to the Cayman Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to the Cayman Islands is January, when tickets cost $498 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $935 and $753 respectively.

What’s the cheapest day of the week to fly from Chicago O'Hare Airport to Cayman Islands?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

When flying from Chicago O'Hare Airport to Cayman Islands, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Chicago O'Hare Airport, you’ll find the best rates on Sundays and the most expensive ones on Wednesdays.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to the Cayman Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago O'Hare Intl Airport to the Cayman Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Chicago O'Hare Intl Airport to the Cayman Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 1 week before departure.

Good to know

Low seasonSeptember
Cheapest flight$102
Most popular time to fly with an average 12% increase in price.
Flight from Chicago O'Hare Airport to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from Chicago O'Hare Airport to Cayman Islands?

    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 Chicago O'Hare Airport to Cayman Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago O'Hare Airport to Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago O'Hare Airport to Cayman Islands 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 Chicago O'Hare Airport to Cayman Islands?

    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 from Chicago O'Hare Airport to Cayman Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago O'Hare Airport to Cayman Islands?

    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 from Chicago O'Hare Airport to Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from O'Hare Intl to the Cayman Islands

 
Need help choosing which airline to fly with from O'Hare Intl to the Cayman Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9428 reviews
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
Airline reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

4.0 OkayDr. Joseph, Feb 2026
ORD - IAH
Read more United Airlines reviews

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

Everything you need to know for your flight from O'Hare Intl to the Cayman Islands

Information on your arrival and departure airports