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Cayman Islands

$125+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Dec 12 — Dec 191
Fri 12/12
Fri 12/19
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 November 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$389
(Southwest)

One-way from

$125
(Southwest)

Popular in

December

Cheapest in

October

Average price

$764
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
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One-way flight from Chicago Midway to Cayman Islands
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Highest demand for flights based on searches. 7% potential increase in price ($58 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/142:59 pmMDW - GCM
1 stop19h 36mMultiple Airlines
Mon 12/227:00 amGCM - MDW
1 stop8h 05mMultiple Airlines
Deal found 11/11$463
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/112:16 pmMDW - GCM
1 stop20h 19mMultiple Airlines
Mon 12/157:00 amGCM - MDW
2 stops26h 46mMultiple Airlines
Deal found 11/11$466
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Tue 12/167:44 amMDW - GCM
2 stops12h 31mMultiple Airlines
Wed 12/247:00 amGCM - MDW
1 stop8h 37mMultiple Airlines
Deal found 11/9$472
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sat 12/62:59 pmMDW - GCM
1 stop19h 36mMultiple Airlines
Sat 12/138:50 amGCM - MDW
1 stop14h 40mMultiple Airlines
Deal found 11/11$478
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sat 12/132:59 pmMDW - GCM
1 stop19h 36mMultiple Airlines
Mon 12/227:00 amGCM - MDW
1 stop8h 05mMultiple Airlines
Deal found 11/11$480
This Kiwi.com deal was found by Cheapflights users on 11/9. 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.
Mon 12/226:12 amMDW - GCM
2 stops14h 03mMultiple Airlines
Wed 12/247:00 amGCM - MDW
1 stop8h 37mMultiple Airlines
Deal found 11/9$492
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 12/186:12 amMDW - GCM
2 stops14h 03mMultiple Airlines
Wed 12/247:00 amGCM - MDW
1 stop8h 37mMultiple Airlines
Deal found 11/9$494
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Sat 12/132:59 pmMDW - GCM
1 stop19h 36mMultiple Airlines
Wed 12/247:00 amGCM - MDW
1 stop8h 37mMultiple Airlines
Deal found 11/11$496
This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/186:33 pmMDW - GCM
2 stops16h 02mMultiple Airlines
Mon 12/227:00 amGCM - MDW
1 stop8h 05mMultiple Airlines
Deal found 11/11$511
This Southwest deal was found by Cheapflights users on 11/10. 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.
Sat 12/137:30 pmMDW - GCM
2 stops16h 05mSouthwest
Tue 12/161:30 pmGCM - MDW
2 stops10h 05mSouthwest
Deal found 11/10$521

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 November 12, 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

Sat 1/3

7:45 am-3:10 pm

1 stop6h 25m

George Town Owen Roberts Intl

Thu 1/8

1:50 pm-10:05 pm

2 stops9h 15m

$389

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 1/24

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Sat 1/31

3:25 pm-10:26 pm

1 stop8h 01m

$411

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/10

6:00 am-11:35 am

1 stop5h 35m

George Town Owen Roberts Intl

Wed 3/11

1:00 pm-8:50 am

2 stops19h 50m

$442

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 1/4

7:20 pm-12:35 pm

2 stops16h 15m

George Town Owen Roberts Intl

Thu 1/8

1:50 pm-10:05 pm

2 stops9h 15m

$446

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/26

6:00 am-11:24 am

1 stop5h 24m

George Town Owen Roberts Intl

Sat 5/2

12:50 pm-9:45 pm

1 stop8h 55m

$462

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 1/17

6:45 am-2:00 pm

1 stop6h 15m

George Town Owen Roberts Intl

Sat 1/24

3:25 pm-10:26 pm

1 stop8h 01m

$507

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 12/21

6:00 am-12:36 pm

1 stop5h 36m

George Town Owen Roberts Intl

Thu 12/25

3:42 pm-10:22 pm

1 stop7h 40m

$528

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 12/18

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Tue 12/23

1:52 pm-10:22 pm

1 stop9h 30m

$528

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 12/21

6:00 am-12:36 pm

1 stop5h 36m

George Town Owen Roberts Intl

Mon 12/22

3:42 pm-10:22 pm

1 stop7h 40m

$528

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 12/11

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Mon 12/15

1:50 pm-11:47 pm

1 stop10h 57m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 21 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 40m. Your travel time can differ by up to 45m. 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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O'Hare Intl to Gustavia flights
Midway to St. John's flights

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