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Find cheap flights from Chicago Midway Airport to Cayman Islands from $163

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Midway to the Cayman Islands departing on 6/5. 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
0 bags
Sun 5/26
Sun 6/2

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Best Cayman Islands Flight Deals

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

George Town
George Town1 stop$480

Good to know

Cheapest flight

$163
Flight from Chicago Midway Airport to George Town

FAQs - booking Cayman Islands flights

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cayman Islands from Chicago Midway Airport 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 Midway 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 to Cayman Islands with an airline and back to Chicago Midway Airport with another airline.

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

  • Morning departure is around 2% 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 airline flying from Midway to the Cayman Islands

 
Need help choosing which airline to fly with from Midway 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.
8.0
DeltaOverall score based on 10966 reviews
8.0entertainment
8.6crew
7.9comfort
8.2boarding
7.4food
Airline reviews

Delta is one of the best airlines I have flown

10.0 ExcellentKellie, Apr 2024ANC - SEA
Read more about Delta reviews

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

Book cheap flights from Chicago to the Cayman Islands

Recent round-trip flight deals

5/26Sun
1 stop
20h 47mMDW-GCM
6/4Tue
1 stop
20h 02mGCM-MDW
$480
8/10Sat
1 stop
22h 27mMDW-GCM
8/14Wed
1 stop
7h 48mGCM-MDW
$483
9/21Sat
1 stop
8h 22mMDW-GCM
9/27Fri
1 stop
12h 18mGCM-MDW
$517
7/7Sun
1 stopDelta
16h 41mMDW-GCM
7/16Tue
1 stopDelta
8h 51mGCM-MDW
$578
7/8Mon
1 stopDelta
5h 30mMDW-GCM
7/16Tue
2 stopsDelta
19h 50mGCM-MDW
$583
7/5Fri
1 stopDelta
5h 35mMDW-GCM
7/11Thu
1 stopDelta
8h 51mGCM-MDW
$603
7/4Thu
2 stopsDelta
17h 50mMDW-GCM
7/10Wed
1 stopDelta
8h 51mGCM-MDW
$608
6/22Sat
2 stopsWestJet
24h 32mMDW-GCM
6/29Sat
2 stopsWestJet
21h 42mGCM-MDW
$2,951
5/10Fri
2 stopsWestJet
21h 05mMDW-GCM
5/12Sun
2 stopsWestJet
25h 05mGCM-MDW
$2,963
6/29Sat
2 stopsWestJet
24h 32mMDW-GCM
7/6Sat
2 stopsWestJet
23h 59mGCM-MDW
$2,969

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Recent one-way flight deals

6/5Wed
1 stop
7h 43mMDW-GCM
$163
6/5Wed
2 stops
28h 57mMDW-GCM
$256
6/5Wed
3 stops
24h 30mMDW-GCM
$542

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Last minute flights from Midway to the Cayman Islands

Last minute flight, train and bus deals

5/1Wed
multi-stop
26h 03mMDW-GCM
5/31Fri
multi-stop
11h 27mGCM-MDW
$588
5/1Wed
multi-stop
24h 32mMDW-GCM
5/31Fri
multi-stop
11h 27mGCM-MDW
$652
4/28Sun
multi-stopDelta
5h 48mMDW-GCM
5/2Thu
multi-stopDelta
9h 42mGCM-MDW
$978
4/28Sun
multi-stopDelta
5h 48mMDW-GCM
5/2Thu
multi-stopDelta
19h 41mGCM-MDW
$983
4/28Sun
multi-stopDelta
22h 23mMDW-GCM
5/2Thu
multi-stopDelta
23h 36mGCM-MDW
$1,007

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Chicago Midway Airport - Cayman Islands Flights

Departure:

Chicago Midway Airport (MDW)United States

Return flight deals:

Cayman Islands - Chicago Midway Airport

Cabin classes: