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Grand Cayman

$275+ Cheap flights from Midway (MDW) to Grand Cayman

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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Aug 18 — Aug 251
Mon 8/18
Mon 8/25
1 adult, Economy
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Cheap flight deals from Midway to Grand Cayman

Keep the following information in mind while searching for Midway to Grand Cayman flight deals. Data was last updated August 13, 2025.

Round-trip from

$410
(Southwest)

One-way from

$275
(Kiwi.com)

Popular in

March

Cheapest in

October

Average price

$739
From Chicago Midway to Grand Cayman
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One-way flight from Chicago Midway to Grand Cayman
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Highest demand for flights based on searches. 7% potential increase in price ($56 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 August 2025
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Find flight deals from Midway to Grand Cayman

Cheapest flights from Midway to Grand Cayman
Explore the most affordable flight options available from Midway to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 13, 2025.

This Southwest deal was found by Cheapflights users on 8/11. 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.
Wed 12/105:05 amMDW - GCM
1 stop6h 30mSouthwest
Wed 12/171:30 pmGCM - MDW
1 stop7h 00mSouthwest
Deal found 8/11$410
This Southwest deal was found by Cheapflights users on 8/11. 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.
Mon 12/155:05 amMDW - GCM
1 stop6h 30mSouthwest
Sat 12/204:10 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 8/11$467
This Southwest deal was found by Cheapflights users on 8/12. 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 12/146:05 pmMDW - GCM
2 stops17h 30mSouthwest
Fri 12/191:30 pmGCM - MDW
1 stop8h 05mSouthwest
Deal found 8/12$500
This Southwest deal was found by Cheapflights users on 8/13. 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.
Tue 11/45:05 amMDW - GCM
1 stop6h 30mSouthwest
Sat 11/81:55 pmGCM - MDW
1 stop7h 00mSouthwest
Deal found 8/13$511
This deal was found by Cheapflights users on 8/13. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/246:00 amMDW - GCM
1 stop5h 30mDelta
Wed 12/313:45 pmGCM - MDW
1 stop7h 20mDelta
Deal found 8/13$520
This Delta deal was found by Cheapflights users on 8/12. 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.
Wed 12/246:00 amMDW - GCM
1 stop5h 30mDelta
Mon 12/293:45 pmGCM - MDW
1 stop7h 20mDelta
Deal found 8/12$545

Cheapflights Fare Finder

 
Customize your flight search to find flights from Midway to Grand Cayman 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 August 13, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Grand Cayman that are best for you.

Fly from

Midway

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/10

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

Wed 12/17

1:30 pm-7:30 pm

1 stop7h 00m

$410

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 12/15

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

Sat 12/20

4:10 pm-11:20 pm

1 stop8h 10m

$467

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 12/14

6:05 pm-12:35 pm

2 stops17h 30m

George Town Owen Roberts Intl

Fri 12/19

1:30 pm-11:05 pm

2 stops10h 35m

$500

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 11/4

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

Sat 11/8

1:55 pm-7:55 pm

1 stop7h 00m

$511

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 1/25

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 1/29

2:00 pm-9:46 pm

1 stop8h 46m

$520

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 10/18

5:20 pm-11:40 am

2 stops18h 20m

$275

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 10/18

6:00 am-11:35 am

1 stop5h 35m

$318

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 8/28

12:20 pm-9:20 pm

2 stops33h 00m

$334

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 8/28

6:00 am-11:31 am

1 stop5h 31m

$865

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/11

Best time to book a flight from Midway to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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 Grand Cayman
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 Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Midway to Grand Cayman 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 Grand Cayman?

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Grand Cayman (average of $467). Flying from Chicago Midway Airport to Grand Cayman 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 Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
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