$163 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 3/18. 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$445

Good to know

Low season

October

High season

March

Cheapest flight

$163
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 31% 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 08m
  • 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 $163 one-way, and $445 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 $163.

  • Which airlines fly to the Cayman Islands?

    United 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 22% more expensive 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 4411 reviews
8.2Boarding
7.6Entertainment
8.1Comfort
8.7Crew
7.1Food
Airline reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

10.0 ExcellentAnonymous, Jan 2025ATL - LGA
Read more Southwest reviews

Gate agents were informative and friendly… flight attendants were as well. Had a fun time chatting about their legacy AirTran experiences as a former fan of the airline that Southwest acquired.

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.

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

I loved having a most black flight crew during Black History Month; rather by design or accident I appreciated the representation. ❤️

This was the second flight this week with flight attendant Marcus I’m not sure if his last name is Lane or Lang but this guy is awesome. He funny, attentive and his service is 5 stars. Marcus makes business travel more enjoyable !

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Rode in a smaller plane and short trip meant no snacks, no free wifi or tv. It was only 30min flight so honestly wasn’t a big deal to lack these items.

Lower number on this flight so spaced out passengers. Able to enjoy more room to relax during flight. It was lovely.

Kind staff. Snacks are small but that’s the new normal.

Overall, terrible. Flight from SFO was delayed due to “air traffic control issues”, and we were all mislead about connecting flights. Told “you have 20 minutes to catch your connection”. Reality was 5. We got to watch the plane sit at the bridge. Won’t fly Delta with a connection again.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

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

Our seats were all the way in back of the plane,

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.

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

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.

Book cheap flights from Chicago to the Cayman Islands

Recent round-trip flight deals

5/7Wed
1 stop
9h 10mORD-GCM
5/16Fri
1 stop
16h 06mGCM-ORD
$445
4/10Thu
1 stop
26h 20mORD-GCM
4/12Sat
1 stop
25h 14mGCM-ORD
$450
5/9Fri
1 stopSouthwest
6h 00mMDW-GCM
5/14Wed
1 stopSouthwest
9h 20mGCM-MDW
$524
5/9Fri
2 stopsSouthwest
19h 00mMDW-GCM
5/14Wed
1 stopSouthwest
9h 20mGCM-MDW
$528
3/20Thu
1 stopUnited Airlines
8h 55mORD-GCM
3/25Tue
nonstopUnited Airlines
4h 16mGCM-ORD
$600
5/6Tue
1 stopDelta
5h 52mORD-GCM
5/21Wed
1 stopDelta
8h 23mGCM-ORD
$601
3/23Sun
1 stopAmerican Airlines
17h 25mORD-GCM
4/3Thu
1 stopAmerican Airlines
11h 27mGCM-ORD
$610
3/25Tue
2 stopsAmerican Airlines
8h 29mORD-GCM
4/1Tue
2 stopsAmerican Airlines
9h 40mGCM-ORD
$614
4/6Sun
nonstopUnited Airlines
3h 55mORD-GCM
4/13Sun
nonstopUnited Airlines
4h 22mGCM-ORD
$620
5/3Sat
1 stopDelta
6h 02mORD-GCM
5/22Thu
1 stopDelta
8h 23mGCM-ORD
$626

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Recent one-way flight deals

3/18Tue
2 stops
29h 26mORD-GCM
$163
5/20Tue
1 stop
9h 10mORD-GCM
$167
4/20Sun
1 stopSouthwest
5h 50mORD-GCM
$217
4/20Sun
2 stopsSouthwest
18h 25mORD-GCM
$241
8/18Mon
1 stopDelta
5h 31mORD-GCM
$293
5/24Sat
nonstopUnited Airlines
4h 04mORD-GCM
$313
4/20Sun
nonstopUnited Airlines
3h 55mORD-GCM
$333
8/19Tue
1 stopAmerican Airlines
5h 30mORD-GCM
$338
3/5Wed
1 stopDelta
5h 53mORD-GCM
$343
3/21Fri
2 stopsAmerican Airlines
8h 29mORD-GCM
$413

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Last minute flights from Chicago to the Cayman Islands

Last minute flight, train and bus deals

2/21Fri
multi-stop
43h 47mORD-GCM
2/27Thu
multi-stop
24h 07mGCM-ORD
$644
2/22Sat
multi-stop
22h 00mORD-GCM
3/1Sat
multi-stop
16h 37mGCM-ORD
$673
2/21Fri
multi-stop
43h 47mORD-GCM
2/27Thu
multi-stop
35h 03mGCM-ORD
$712
2/21Fri
multi-stop
43h 47mORD-GCM
2/27Thu
multi-stop
37h 28mGCM-ORD
$736
2/22Sat
multi-stop
22h 25mORD-GCM
3/1Sat
multi-stop
16h 37mGCM-ORD
$760
2/22Sat
multi-stopDelta
7h 20mORD-GCM
2/26Wed
multi-stopDelta
10h 45mGCM-ORD
$950
2/22Sat
multi-stopDelta
9h 35mORD-GCM
2/26Wed
multi-stopDelta
10h 45mGCM-ORD
$954
2/22Sat
multi-stopAmerican Airlines
15h 51mORD-GCM
3/1Sat
multi-stopAmerican Airlines
17h 23mGCM-ORD
$970
2/22Sat
nonstopAmerican Airlines
3h 55mORD-GCM
3/1Sat
multi-stopAmerican Airlines
17h 23mGCM-ORD
$990
2/22Sat
nonstopUnited Airlines
3h 56mORD-GCM
3/1Sat
nonstopUnited Airlines
4h 16mGCM-ORD
$1,025

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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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