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Grand Cayman

$227+ 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 12/13. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$356
(Delta)

One-way from

$285
(Southwest)

Popular in

March

Cheapest in

October

Average price

$569
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 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. 6% potential increase in price ($44 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($14 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 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 September 29, 2025.

This Southwest deal was found by Cheapflights users on 9/28. 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 12/67:30 pmMDW - GCM
2 stops16h 05mSouthwest
Wed 12/101:30 pmGCM - MDW
1 stop7h 05mSouthwest
Deal found 9/28$459
This Southwest deal was found by Cheapflights users on 9/29. 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
Fri 12/191:30 pmGCM - MDW
1 stop6h 45mSouthwest
Deal found 9/29$461
This Southwest deal was found by Cheapflights users on 9/28. 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 12/62:45 pmMDW - GCM
2 stops20h 50mSouthwest
Thu 12/111:30 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 9/28$484
This Trip.com deal was found by Cheapflights users on 9/27. 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.
Fri 10/1012:28 pmMDW - GCM
1 stop8h 47mMultiple Airlines
Mon 10/134:45 pmGCM - MDW
1 stop7h 01mMultiple Airlines
Deal found 9/27$497
This Southwest deal was found by Cheapflights users on 9/27. 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 11/155:05 amMDW - GCM
1 stop6h 55mSouthwest
Sat 11/224:10 pmGCM - MDW
1 stop8h 10mSouthwest
Deal found 9/27$540
This Southwest deal was found by Cheapflights users on 9/28. 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.
Thu 11/135:50 amMDW - GCM
1 stop5h 45mSouthwest
Sun 11/161:30 pmGCM - MDW
2 stops11h 40mSouthwest
Deal found 9/28$548
This Delta deal was found by Cheapflights users on 9/29. 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 10/136:00 amMDW - GCM
1 stop5h 35mDelta
Fri 10/1712:55 pmGCM - MDW
1 stop9h 19mDelta
Deal found 9/29$552

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 September 29, 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 2/4

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 2/5

2:00 pm-9:46 pm

1 stop8h 46m

$356

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/3

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Fri 2/6

2:00 pm-9:46 pm

1 stop8h 46m

$356

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 2/8

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Fri 2/13

2:00 pm-9:46 pm

1 stop8h 46m

$356

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/17

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Tue 2/24

2:00 pm-9:46 pm

1 stop8h 46m

$356

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/3

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 2/5

2:00 pm-9:46 pm

1 stop8h 46m

$356

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/3

5:59 pm-12:35 pm

2 stops17h 36m

George Town Owen Roberts Intl

Tue 2/10

2:00 pm-9:46 pm

1 stop8h 46m

$360

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/2

1:00 pm-12:35 pm

2 stops22h 35m

George Town Owen Roberts Intl

Wed 2/11

2:00 pm-8:50 am

2 stops19h 50m

$360

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/2

9:30 am-12:35 pm

2 stops26h 05m

George Town Owen Roberts Intl

Thu 2/5

2:00 pm-8:50 am

2 stops19h 50m

$360

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 2/1

1:00 pm-12:35 pm

2 stops22h 35m

George Town Owen Roberts Intl

Fri 2/6

2:00 pm-9:46 pm

1 stop8h 46m

$360

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 2/2

5:59 pm-12:35 pm

2 stops17h 36m

George Town Owen Roberts Intl

Tue 2/10

2:00 pm-9:46 pm

1 stop8h 46m

$360

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 18 results
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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.

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

    Delta can get you from Chicago Midway Airport to Grand Cayman in just under 5h 35m. Your travel time can differ by up to . The distance between Chicago Midway Airport and Grand Cayman is about 1598 mi.

  • 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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Midway to George Town flights
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