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Find cheap flights from Chicago Midway Airport to Cayman Islands from $158

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 6/11. 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
0 bags
Wed 6/5
Wed 6/12

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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$481

Good to know

Cheapest flight

$158
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 8% 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 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 10818 reviews
8.6Crew
7.9Comfort
7.4Food
8.2Boarding
8.0Entertainment
Airline reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

2.0 MediocreAnonymous, May 2024AVL - LGA
Read more about Delta reviews

The gate area was incredibly short staffed, with one representative manning 4-5 flights, which caused a 3 hr delay in boarding even though the plane was all ready to leave. Other flights also were delayed because of this. The flight crew was awesome and I feel bad for the only gate worker on call, but Delta needs to hire more employees.

Very frustrated with boarding gate crew. She announced the plane was small and they would be limiting us to one item to carry on. Not a problem for me as I understand the tiny planes have limited space!! Not the case here! It was a rather large plane and had plenty of room for bags! So because I don’t want to be one of “those people” who ignores the request to check a carry on I did so asking if I would be able to pick it up at the bottom of the ramp on arrival in Knoxville to which she responded “yes”! Then I watched as every other passenger held onto their 2 items and boarded!! Then when we arrived in Knoxville our 2 carry ons had been put with all the other luggage and we had to go to baggage pick up and wait for all the big checked bags to come off the carousel! So she lied!! Frustrating. Next time I won’t be so nice!

It was a good experience except when boarding a female flight attendant did not go out of her way to assist my teenage daughters in finding space for their carry-ons after their compartments were full.

On time departure, smooth trip, flight attendant told through passengers the gate we would arrive at and the gate our outbound flight was departing from. Early arrival

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

Book cheap flights from Chicago to the Cayman Islands

Recent round-trip flight deals

6/11Tue
1 stop
20h 34mMDW-GCM
6/16Sun
1 stop
17h 31mGCM-MDW
$481
5/27Mon
1 stop
20h 47mMDW-GCM
5/31Fri
1 stop
11h 27mGCM-MDW
$492
5/26Sun
1 stop
20h 47mMDW-GCM
6/3Mon
1 stop
8h 57mGCM-MDW
$509
9/6Fri
1 stopDelta
5h 30mMDW-GCM
9/13Fri
1 stopDelta
8h 54mGCM-MDW
$603
9/6Fri
1 stopDelta
5h 30mMDW-GCM
9/13Fri
2 stopsDelta
19h 55mGCM-MDW
$608
8/21Wed
1 stopDelta
22h 25mMDW-GCM
8/25Sun
1 stopDelta
8h 57mGCM-MDW
$611
10/25Fri
1 stopDelta
16h 40mMDW-GCM
10/27Sun
1 stopDelta
8h 54mGCM-MDW
$635
5/24Fri
2 stopsWestJet
41h 34mMDW-GCM
6/2Sun
2 stopsWestJet
25h 05mGCM-MDW
$2,941
6/29Sat
2 stopsWestJet
25h 58mMDW-GCM
7/6Sat
2 stopsWestJet
23h 59mGCM-MDW
$2,978
10/25Fri
2 stopsWestJet
22h 40mMDW-GCM
10/27Sun
2 stopsWestJet
23h 26mGCM-MDW
$3,012

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Recent one-way flight deals

6/11Tue
1 stop
20h 34mMDW-GCM
$158
6/6Thu
1 stop
6h 44mMDW-GCM
$190
6/10Mon
1 stop
7h 43mMDW-GCM
$208
6/9Sun
1 stop
25h 44mMDW-GCM
$216
6/8Sat
1 stop
24h 14mMDW-GCM
$267
6/10Mon
2 stopsDelta
17h 50mMDW-GCM
$277
6/6Thu
2 stopsDelta
17h 48mMDW-GCM
$302
6/12Wed
2 stopsDelta
22h 11mMDW-GCM
$328
6/8Sat
2 stopsWestJet
26h 03mMDW-GCM
$340
6/9Sun
2 stopsDelta
17h 50mMDW-GCM
$418

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Last minute flights from Midway to the Cayman Islands

Last minute flight, train and bus deals

5/9Thu
multi-stop
16h 27mMDW-GCM
5/14Tue
multi-stop
6h 53mGCM-MDW
$594
5/10Fri
multi-stop
19h 35mMDW-GCM
5/14Tue
multi-stop
6h 53mGCM-MDW
$672
5/10Fri
multi-stop
19h 35mMDW-GCM
5/13Mon
multi-stop
8h 57mGCM-MDW
$790
5/10Fri
multi-stop
21h 18mMDW-GCM
5/13Mon
multi-stop
8h 57mGCM-MDW
$852
5/11Sat
multi-stopDelta
5h 26mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$898
5/8Wed
multi-stopDelta
5h 26mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$963
5/8Wed
multi-stopDelta
17h 39mMDW-GCM
5/12Sun
multi-stopDelta
9h 10mGCM-MDW
$968
5/8Wed
multi-stopDelta
17h 39mMDW-GCM
5/12Sun
multi-stopDelta
28h 15mGCM-MDW
$991
5/10Fri
multi-stop
20h 11mMDW-GCM
5/14Tue
multi-stop
6h 53mGCM-MDW
$1,126

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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: