$175 Find Cheap Flights from Chicago to the 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 Chicago to the Cayman Islands departing on 2/17. 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.
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Best Cayman Islands Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

George Town
George Town1 stop$462

Good to know

Low season

October

High season

March

Cheapest flight

$175
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Chicago O'Hare Airport to George Town

FAQs - booking Cayman Islands flights

  • How long is the flight to the Cayman Islands from Chicago?

    Flights to George Town4h 05m
  • What is the cheapest flight to the Cayman Islands from Chicago?

    The cheapest ticket to the Cayman Islands from Chicago found in the last 72 hours was $175 one-way, and $462 round-trip. The most popular route is from Chicago to George Town, and the cheapest round-trip airline ticket found on this route in the last 72 hours was $175.

  • Which airlines fly to the Cayman Islands?

    American Airlines flies most frequently to George Town from Chicago.

  • How does KAYAK find such low prices on flights from Chicago to the 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 to the Cayman Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to the 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 to the 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 to the 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 to the 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 to the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to the Cayman Islands

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be February, March and April. The cheapest month to fly from Chicago is September.
  • Morning departure is around 6% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 4 airlines serving from Chicago to the Cayman Islands

Need help choosing which airline to fly with from Chicago 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.
8.1
SouthwestOverall score based on 4662 reviews
8.1Comfort
8.2Boarding
7.2Food
8.7Crew
7.7Entertainment
Airline reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

Book cheap flights from Chicago to the Cayman Islands

Recent round-trip flight deals

2/24Mon
1 stop
27h 24mORD-GCM
2/27Thu
1 stop
24h 07mGCM-ORD
$462
2/20Thu
1 stop
12h 55mMDW-GCM
2/25Tue
2 stops
20h 37mGCM-MDW
$464
3/12Wed
2 stopsSouthwest
18h 45mMDW-GCM
3/19Wed
2 stopsSouthwest
20h 40mGCM-MDW
$576
3/12Wed
1 stopUnited Airlines
10h 10mORD-GCM
3/19Wed
nonstopUnited Airlines
4h 16mGCM-ORD
$590
3/12Wed
2 stopsSouthwest
17h 15mMDW-GCM
3/19Wed
1 stopSouthwest
7h 10mGCM-MDW
$590
3/23Sun
1 stopAmerican Airlines
16h 02mORD-GCM
4/3Thu
1 stopAmerican Airlines
17h 25mGCM-ORD
$600
3/12Wed
1 stopDelta
5h 38mMDW-GCM
3/19Wed
1 stopDelta
9h 20mGCM-MDW
$600
3/25Tue
2 stopsAmerican Airlines
8h 29mORD-GCM
4/1Tue
2 stopsAmerican Airlines
10h 02mGCM-ORD
$604
3/5Wed
1 stopDelta
5h 53mORD-GCM
3/19Wed
1 stopDelta
10h 53mGCM-ORD
$610
3/6Thu
nonstopUnited Airlines
3h 57mORD-GCM
3/13Thu
nonstopUnited Airlines
4h 16mGCM-ORD
$680

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Recent one-way flight deals

2/17Mon
1 stop
27h 24mORD-GCM
$175
4/22Tue
1 stop
9h 10mORD-GCM
$176
3/1Sat
1 stop
23h 45mORD-GCM
$184
2/22Sat
1 stop
22h 51mMDW-GCM
$185
3/28Fri
2 stopsSouthwest
14h 00mMDW-GCM
$262
3/5Wed
1 stopDelta
5h 53mORD-GCM
$293
2/22Sat
nonstopAmerican Airlines
3h 55mORD-GCM
$313
7/18Fri
1 stopDelta
5h 31mORD-GCM
$318
3/18Tue
nonstopUnited Airlines
3h 57mORD-GCM
$333
3/23Sun
1 stopUnited Airlines
17h 40mORD-GCM
$338

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Last minute flights from Chicago to the Cayman Islands

Last minute flight, train and bus deals

1/26Sun
multi-stop
7h 44mORD-GCM
2/2Sun
multi-stop
27h 53mGCM-ORD
$586
1/26Sun
multi-stop
6h 25mMDW-GCM
2/2Sun
multi-stop
28h 32mGCM-MDW
$622
1/26Sun
multi-stop
6h 25mMDW-GCM
2/2Sun
multi-stop
32h 05mGCM-MDW
$623
1/26Sun
multi-stop
7h 44mORD-GCM
2/2Sun
multi-stop
25h 11mGCM-ORD
$638
1/26Sun
multi-stop
7h 44mORD-GCM
2/2Sun
multi-stop
27h 10mGCM-ORD
$718
1/25Sat
multi-stop
19h 52mORD-GCM
1/29Wed
multi-stop
32h 51mGCM-ORD
$861
1/25Sat
multi-stopAmerican Airlines
17h 05mORD-GCM
1/29Wed
multi-stopAmerican Airlines
12h 27mGCM-ORD
$920
1/25Sat
nonstopAmerican Airlines
4h 10mORD-GCM
1/29Wed
multi-stopAmerican Airlines
12h 27mGCM-ORD
$940
1/26Sun
multi-stop
13h 00mORD-GCM
2/2Sun
multi-stop
27h 10mGCM-ORD
$943
1/26Sun
multi-stopWestJet
23h 23mMDW-GCM
2/2Sun
multi-stopWestJet
22h 52mGCM-MDW
$3,446

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Everything you need to know for your flight from Chicago to the Cayman Islands

Cabin class types available on flights to the Cayman Islands

Cabin classes available on flights to the Cayman Islands. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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