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Cayman Islands

$171+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
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Cheap 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 septiembre 16, 2025.

Round-trip from

$446
(Southwest)

One-way from

$171
(Southwest)

Popular in

December

Cheapest in

October

Average price

$569
From Chicago Midway to Cayman Islands
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One-way flight from Chicago Midway to Cayman Islands
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Highest demand for flights based on searches. 8% potential increase in price ($59 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 septiembre 16, 2025.

This Southwest deal was found by Cheapflights users on 9/14. 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.
dom. 12/75:50 amMDW - GCM
1 stop5h 45mSouthwest
vie. 12/121:30 pmGCM - MDW
2 stops11h 00mSouthwest
Deal found 9/14$450
This Southwest deal was found by Cheapflights users on 9/15. 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.
lun. 12/155:05 amMDW - GCM
1 stop6h 30mSouthwest
vie. 12/191:30 pmGCM - MDW
1 stop6h 45mSouthwest
Deal found 9/15$483
This Trip.com deal was found by Cheapflights users on 9/16. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/98:00 amMDW - GCM
1 stop7h 05mMultiple Airlines
mar. 12/167:00 amGCM - MDW
1 stop9h 30mMultiple Airlines
Deal found 9/16$493
This Delta deal was found by Cheapflights users on 9/15. 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.
lun. 9/296:00 amMDW - GCM
1 stop5h 36mDelta
jue. 10/212:52 pmGCM - MDW
1 stop8h 44mDelta
Deal found 9/15$514
This Delta deal was found by Cheapflights users on 9/15. 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.
lun. 9/296:00 amMDW - GCM
1 stop5h 36mDelta
vie. 10/312:52 pmGCM - MDW
2 stops19h 48mDelta
Deal found 9/15$518
This Delta deal was found by Cheapflights users on 9/15. 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.
dom. 9/286:00 amMDW - GCM
1 stop5h 36mDelta
jue. 10/212:52 pmGCM - MDW
1 stop8h 44mDelta
Deal found 9/15$526
This Delta deal was found by Cheapflights users on 9/14. 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.
lun. 12/156:00 amMDW - GCM
1 stop5h 35mDelta
dom. 12/283:42 pmGCM - MDW
1 stop7h 34mDelta
Deal found 9/14$536
This Delta deal was found by Cheapflights users on 9/15. 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.
lun. 9/296:00 amMDW - GCM
1 stop5h 36mDelta
sáb. 10/412:52 pmGCM - MDW
1 stop8h 18mDelta
Deal found 9/15$539

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 septiembre 16, 2025.
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

dom. 12/7

9:40 pm-12:35 pm

2 stops13h 55m

George Town Owen Roberts Intl

vie. 12/12

1:30 pm-12:10 am

2 stops11h 40m

$450

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

lun. 12/15

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

vie. 12/19

1:30 pm-8:35 pm

1 stop8h 05m

$483

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 1/4

5:20 am-12:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

jue. 1/8

1:50 pm-9:00 pm

1 stop8h 10m

$483

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mar. 12/9

8:00 am-4:05 pm

1 stop7h 05m

George Town Owen Roberts Intl

mar. 12/16

7:00 am-3:30 pm

1 stop9h 30m

$493

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

lun. 9/29

6:00 am-11:36 am

1 stop5h 36m

George Town Owen Roberts Intl

jue. 10/2

12:52 pm-9:36 pm

1 stop8h 44m

$514

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

lun. 9/29

6:00 am-11:36 am

1 stop5h 36m

George Town Owen Roberts Intl

vie. 10/3

12:52 pm-8:40 am

2 stops19h 48m

$518

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 1/21

7:50 pm-12:55 pm

2 stops16h 05m

$171

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jue. 9/25

4:56 pm-11:35 am

2 stops18h 39m

$204

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jue. 1/22

5:00 am-12:55 pm

1 stop6h 55m

$241

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 1/21

6:45 pm-4:25 pm

3 stops20h 40m

$361

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 11 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 can get you from Chicago Midway Airport to Cayman Islands in just under 13h 55m. Your travel time can differ by up to . There are 1598 mi between Chicago Midway Airport and Cayman Islands.

  • 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.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cayman Islands (average of $467). Flying from Chicago Midway Airport to Cayman Islands in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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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O'Hare Intl to Gregory Town flights
O'Hare Intl to Pointe-à-Pitre flights
O'Hare Intl to The Valley flights
O'Hare Intl to Marsh Harbour flights
Midway to St. John's flights
O'Hare Intl to Gustavia flights

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