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Cayman Islands

$281+ 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 7/5. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$489
(Southwest)

One-way from

$281
(Southwest)

Popular in

March

Cheapest in

September

Average price

$655
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. 11% potential increase in price ($83 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Southwest deal was found by Cheapflights users on 6/11. 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.
Sat 11/17:20 pmMDW - GCM
2 stops17h 15mSouthwest
Thu 11/61:30 pmGCM - MDW
1 stop10h 20mSouthwest
Deal found 6/11$489
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/196:00 amMDW - GCM
1 stop5h 42mDelta
Thu 10/301:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 6/10$520
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/56:21 amMDW - GCM
1 stop9h 39mMultiple Airlines
Tue 9/911:30 amGCM - MDW
2 stops11h 28mMultiple Airlines
Deal found 6/10$654

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 June 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 11/1

7:20 pm-12:35 pm

2 stops17h 15m

George Town Owen Roberts Intl

Thu 11/6

1:30 pm-10:50 pm

1 stop10h 20m

$489

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 10/19

6:00 am-11:42 am

1 stop5h 42m

George Town Owen Roberts Intl

Thu 10/30

1:02 pm-9:44 pm

1 stop8h 42m

$520

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 9/5

6:21 am-4:00 pm

1 stop9h 39m

George Town Owen Roberts Intl

Tue 9/9

11:30 am-10:58 pm

2 stops11h 28m

$654

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 7/5

5:25 am-12:10 pm

1 stop6h 45m

$281

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 11/22

12:55 pm-1:49 pm

1 stop23h 54m

$299

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 11/22

2:00 pm-1:49 pm

3 stops22h 49m

$506

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 7/25

6:00 am-11:22 am

1 stop5h 22m

$745

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and WestJet from Chicago to Cayman Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
WestJet
7.2
Good
2,868 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Entertainment

7.6

Comfort

8.0

Food

7.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Cayman Islands one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $281. Users have also found prices from $506 and $745 on WestJet and Delta, respectively.

  • 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.

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