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Cayman Islands

$127+ Cheap flights from Midway (MDW) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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Cheap flight deals from Midway to Cayman Islands

Cheapest flights from Midway to Cayman Islands
Explore the most affordable flight options available from Midway to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:15 am
MDW
-
GCM
1 stop14h 00m
Multiple Airlines
Thu 3/127:00 am
GCM
-
MDW
1 stop6h 41m
Multiple Airlines
Deal found 2/9$387
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:15 am
MDW
-
GCM
1 stop14h 00m
Multiple Airlines
Sun 3/12:49 pm
GCM
-
MDW
2 stops32h 40m
Multiple Airlines
Deal found 2/11$407
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:30 am
MDW
-
GCM
1 stop10h 30m
Multiple Airlines
Tue 3/1711:30 am
GCM
-
MDW
2 stops22h 55m
Multiple Airlines
Deal found 2/10$411
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:15 am
MDW
-
GCM
1 stop28h 20m
Multiple Airlines
Thu 3/194:45 pm
GCM
-
MDW
2 stops29h 34m
Multiple Airlines
Deal found 2/11$432
This Southwest deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:05 am
MDW
-
GCM
1 stop5h 55m
Southwest
Tue 3/1712:40 pm
GCM
-
MDW
1 stop6h 40m
Southwest
Deal found 2/11$455
This Southwest deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:10 pm
MDW
-
GCM
2 stops22h 30m
Southwest
Tue 4/211:05 pm
GCM
-
MDW
2 stops10h 00m
Southwest
Deal found 2/9$464
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:35 am
MDW
-
GCM
1 stop6h 35m
Southwest
Sat 4/181:05 pm
GCM
-
MDW
1 stop9h 10m
Southwest
Deal found 2/10$473
This Delta deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/206:00 am
MDW
-
GCM
1 stop6h 00m
Delta
Thu 4/301:25 pm
GCM
-
MDW
2 stops23h 18m
Delta
Deal found 2/11$508
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
MDW
-
GCM
1 stop6h 00m
Delta
Tue 4/281:25 pm
GCM
-
MDW
1 stop9h 03m
Delta
Deal found 2/10$515

Find flight deals from Midway to Cayman Islands

Keep the following information in mind while searching for Midway to Cayman Islands flight deals. Data was last updated February 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$387
(Kiwi.com)

One-way from

$127
(Southwest)

Popular in

December

Cheapest in

February

Average price

$527
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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From Chicago Midway to Cayman Islands
Search Deals
One-way flight from Chicago Midway to Cayman Islands
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in February 2026
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Cayman Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 12, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to the Cayman Islands that are best for you.

Fly from

Midway

Fly to

Cayman Islands

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/8

6:05 am-12:00 pm

1 stop5h 55m

George Town Owen Roberts Intl

Tue 3/17

12:40 pm-7:20 pm

1 stop6h 40m

$455

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/8

7:30 am-6:00 pm

1 stop10h 30m

George Town Owen Roberts Intl

Tue 3/17

4:25 pm-10:05 am

1 stop17h 40m

$455

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 4/17

4:10 pm-2:40 pm

2 stops22h 30m

George Town Owen Roberts Intl

Tue 4/21

1:05 pm-11:05 pm

2 stops10h 00m

$464

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 4/13

5:35 am-12:10 pm

1 stop6h 35m

George Town Owen Roberts Intl

Sat 4/18

1:05 pm-10:15 pm

1 stop9h 10m

$473

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 4/20

6:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Wed 4/29

1:25 pm-10:28 pm

1 stop9h 03m

$508

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/26

6:38 pm-12:00 pm

2 stops17h 22m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:28 pm

1 stop9h 03m

$508

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 4/22

6:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:28 pm

1 stop9h 03m

$508

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 4/22

6:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Wed 4/29

1:25 pm-10:28 pm

1 stop9h 03m

$508

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 4/20

6:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:28 pm

1 stop9h 03m

$508

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 4/21

6:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Thu 4/30

1:25 pm-10:28 pm

1 stop9h 03m

$508

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 14 results
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Best time to book a flight from Midway to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Midway with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago Midway Airport to the Cayman Islands
No data available for this route at this time. Please check back soon.

Related info for your journey

Find useful and relevant information for your journey from Midway to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Southwest and Delta can get you from Chicago Midway Airport to Cayman Islands in just under 5h 55m. Your travel time can differ by up to 05m. There are 1598 mi between Chicago Midway Airport and Cayman Islands. This flight may include one or multiple stops.

  • Can I find deals for flights from Midway to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Midway to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Midway to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Midway to Cayman Islands.

  • Can I find deals for business class flights from Midway to Cayman Islands?

    Yes. Cheapflights offers flight deals from Midway to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Alternative routes for Midway to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Midway to Kingston flights
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Midway to Santiago de los Caballeros flights
Midway to St. John's flights
Midway to Georgetown flights

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