$178 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 1/21. 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$489

Good to know

Low season

October

High season

March

Cheapest flight

$178
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly with an average 25% 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 06m
  • 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 $178 one-way, and $489 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 $178.

  • 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 February.
  • Morning departure is around 37% 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 4821 reviews
8.7Crew
7.2Food
7.7Entertainment
8.2Boarding
8.1Comfort
Airline reviews

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.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

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

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

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?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Logan airport construction meant that boarding was chaotic crowded and delayed

Everything was great. Great service, excellent communication, and early arrival

We were forced to wait nearly 50 additional minutes before leaving the terminal.

Free Wi-Fi is good. That’s all - food mediocre, unfriendly crew, poor communication after trying to file a claim for my lost bag, which Delta didn’t even know was lost until I told them.

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

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

late departure due to some unspecified issue with ventilating the cabin. They got it running but it was FREEZING for the whole flight. I asked for a blanket but they didn't provide one. They could not turn up the heat. it was quite miserable.

We were delayed because of ground crew, not because the plane wasn’t ready to go. The food was better than usual!

I still prefer Delta, but Delta doesn’t fly to State College PA.

Everything was fantastic. Modern plane. All the amenities! Although the paid snacks and meals are pure robbery. Like i understand airlines need to make money, but 11$ USD for an overnight oats with some nuts in it and barely any pieces of apple.... Highway robbery

United needs to figure out its Economy PLUS standards; its better than economy but that's not saying much. It seems like United stripped away all the basics for an international flight (such as In Seat entertainment) and repackaged some of them as plus. Would not fly United internationally again.

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.

The flight was delayed till next day ! They kept delaying every 30 minutes then after 3 hours they delayed it till next day. We kept waiting in line standing more than an hour to get the hotel and meal vouchers. There was no communication at all. Everything was bad

Smoothe flight. Pilot and crew did a great job. Uncomfortable seat in this jet, felt worn out

seats were way too small. Too short of a flight to offer amenities.

Book cheap flights from Chicago to the Cayman Islands

Recent round-trip flight deals

1/9Thu
1 stop
20h 38mORD-GCM
1/14Tue
1 stop
25h 59mGCM-ORD
$489
1/9Thu
1 stop
20h 38mORD-GCM
1/14Tue
2 stops
25h 17mGCM-ORD
$495
1/9Thu
1 stopSouthwest
6h 20mMDW-GCM
1/14Tue
1 stopSouthwest
6h 55mGCM-MDW
$526
1/9Thu
1 stopSouthwest
6h 20mMDW-GCM
1/14Tue
2 stopsSouthwest
9h 50mGCM-MDW
$531
4/26Sat
1 stopAmerican Airlines
16h 06mORD-GCM
4/30Wed
1 stopAmerican Airlines
7h 55mGCM-ORD
$598
3/25Tue
1 stopDelta
5h 25mMDW-GCM
4/1Tue
1 stopDelta
9h 37mGCM-MDW
$598
4/26Sat
1 stopAmerican Airlines
16h 06mORD-GCM
4/30Wed
2 stopsAmerican Airlines
10h 37mGCM-ORD
$603
3/26Wed
1 stopDelta
5h 25mMDW-GCM
4/2Wed
1 stopDelta
9h 37mGCM-MDW
$643
1/18Sat
nonstopUnited Airlines
3h 56mORD-GCM
1/25Sat
nonstopUnited Airlines
4h 16mGCM-ORD
$644
3/6Thu
nonstopUnited Airlines
3h 57mORD-GCM
3/14Fri
nonstopUnited Airlines
4h 16mGCM-ORD
$674

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Recent one-way flight deals

1/21Tue
1 stop
25h 08mORD-GCM
$178
1/21Tue
1 stop
25h 08mORD-GCM
$179
3/2Sun
2 stopsSouthwest
15h 20mMDW-GCM
$217
2/18Tue
1 stopDelta
5h 53mORD-GCM
$292
12/25Wed
1 stopSouthwest
5h 55mMDW-GCM
$305
1/18Sat
nonstopAmerican Airlines
4h 10mORD-GCM
$313
2/8Sat
1 stopDelta
5h 38mMDW-GCM
$317
3/17Mon
nonstopUnited Airlines
3h 57mORD-GCM
$333
5/25Sun
2 stopsAmerican Airlines
7h 18mORD-GCM
$337
1/18Sat
nonstopUnited Airlines
3h 56mORD-GCM
$358

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Last minute flights from Chicago to the Cayman Islands

Last minute flight, train and bus deals

12/21Sat
multi-stopSouthwest
6h 05mORD-GCM
12/26Thu
multi-stopSouthwest
9h 10mGCM-ORD
$704
12/23Mon
multi-stopSouthwest
6h 10mORD-GCM
12/29Sun
multi-stopSouthwest
9h 10mGCM-ORD
$724
12/23Mon
multi-stop
11h 40mMDW-GCM
12/29Sun
multi-stop
26h 21mGCM-MDW
$732
12/25Wed
multi-stop
33h 15mMDW-GCM
12/29Sun
multi-stop
7h 36mGCM-MDW
$847
12/25Wed
multi-stopDelta
7h 47mORD-GCM
12/29Sun
multi-stopDelta
9h 06mGCM-ORD
$883
12/24Tue
multi-stopUnited Airlines
8h 00mORD-GCM
12/30Mon
nonstopUnited Airlines
4h 16mGCM-ORD
$908
12/24Tue
multi-stopUnited Airlines
9h 25mORD-GCM
12/30Mon
multi-stopUnited Airlines
8h 27mGCM-ORD
$918
12/25Wed
multi-stopAmerican Airlines
8h 05mORD-GCM
12/29Sun
multi-stopAmerican Airlines
10h 34mGCM-ORD
$938
12/24Tue
multi-stopDelta
7h 52mORD-GCM
12/31Tue
multi-stopDelta
9h 09mGCM-ORD
$963
12/24Tue
multi-stopAmerican Airlines
6h 00mORD-GCM
12/31Tue
multi-stopAmerican Airlines
11h 51mGCM-ORD
$973

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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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