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Cayman Islands

$412+ Cheap flights from Midway (MDW) to the Cayman Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
ene. 26 — feb. 21
lun. 1/26
lun. 2/2
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 diciembre 27, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
mié. 12/313:32 pmMDW - GCM
1 stop19h 03mMultiple Airlines
mié. 1/1411:30 amGCM - MDW
2 stops11h 49mMultiple Airlines
Deal found 12/26$609
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
mar. 12/302:01 pmMDW - GCM
2 stops25h 04mMultiple Airlines
mar. 1/611:30 amGCM - MDW
1 stop27h 36mMultiple Airlines
Deal found 12/26$628
This Southwest deal was found by Cheapflights users on 12/26. 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.
mié. 12/315:05 amMDW - GCM
1 stop6h 30mSouthwest
mié. 1/141:50 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 12/26$679
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
lun. 12/296:15 amMDW - GCM
1 stop14h 00mMultiple Airlines
mar. 1/611:30 amGCM - MDW
1 stop27h 36mMultiple Airlines
Deal found 12/26$728
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
lun. 12/296:15 amMDW - GCM
1 stop14h 00mMultiple Airlines
dom. 1/42:40 pmGCM - MDW
2 stops23h 41mMultiple Airlines
Deal found 12/26$820
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
mar. 12/302:01 pmMDW - GCM
2 stops25h 04mMultiple Airlines
lun. 1/57:00 amGCM - MDW
1 stop8h 05mMultiple Airlines
Deal found 12/26$908
This Delta deal was found by Cheapflights users on 12/26. 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.
mar. 12/306:00 amMDW - GCM
1 stop5h 36mDelta
mar. 1/62:05 pmGCM - MDW
1 stop9h 02mDelta
Deal found 12/26$965
This Delta deal was found by Cheapflights users on 12/26. 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.
mié. 12/316:08 pmMDW - GCM
2 stops19h 19mDelta
mar. 1/62:05 pmGCM - MDW
1 stop9h 02mDelta
Deal found 12/26$970
This Kiwi.com deal was found by Cheapflights users on 12/26. 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.
lun. 12/296:15 amMDW - GCM
1 stop14h 00mMultiple Airlines
lun. 1/57:00 amGCM - MDW
1 stop8h 05mMultiple Airlines
Deal found 12/26$1,007
This Delta deal was found by Cheapflights users on 12/26. 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. 12/296:08 pmMDW - GCM
2 stops19h 19mDelta
mar. 1/62:05 pmGCM - MDW
1 stop9h 02mDelta
Deal found 12/26$1,020
This Delta deal was found by Cheapflights users on 12/25. 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. 12/296:00 amMDW - GCM
1 stop7h 27mDelta
jue. 1/13:42 pmGCM - MDW
1 stop7h 40mDelta
Deal found 12/25$1,055

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 diciembre 27, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$412
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$807
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Chicago Midway to Cayman Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 diciembre 27, 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

jue. 2/12

3:00 pm-9:15 pm

2 stops29h 15m

George Town Owen Roberts Intl

jue. 2/19

7:00 am-1:56 pm

1 stop7h 56m

$412

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 2/1

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

jue. 2/5

2:05 pm-10:22 pm

1 stop9h 17m

$452

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 1/7

3:01 pm-11:35 am

1 stop19h 34m

George Town Owen Roberts Intl

lun. 1/12

7:00 am-2:06 pm

1 stop8h 06m

$457

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 1/25

5:30 am-12:55 pm

1 stop6h 25m

George Town Owen Roberts Intl

dom. 2/1

1:50 pm-10:25 pm

1 stop9h 35m

$482

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jue. 1/29

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

mar. 2/3

2:05 pm-10:22 pm

1 stop9h 17m

$482

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jue. 1/29

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

mar. 2/3

1:50 pm-10:05 pm

2 stops9h 15m

$487

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 2/1

5:30 am-12:55 pm

1 stop6h 25m

George Town Owen Roberts Intl

jue. 2/5

1:50 pm-10:30 pm

2 stops9h 40m

$510

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 1/24

6:25 am-2:00 pm

1 stop6h 35m

George Town Owen Roberts Intl

sáb. 1/31

2:05 pm-10:22 pm

1 stop9h 17m

$512

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mar. 2/3

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

dom. 2/8

1:50 pm-9:00 pm

1 stop8h 10m

$529

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

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?

    Delta and Southwest 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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