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Cayman Islands

$298+ 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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$617
(Kiwi.com)

One-way from

$298
(Delta)

Popular in

March

Cheapest in

September

Average price

$648
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. 8% potential increase in price ($62 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 April 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 April 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/17. 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 6/14:06 pmMDW - GCM
1 stop25h 14mMultiple Airlines
Sun 6/812:40 pmGCM - MDW
1 stop9h 52mMultiple Airlines
Deal found 4/17$617
This Delta deal was found by Cheapflights users on 4/17. 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 12/16:00 amMDW - GCM
1 stop5h 37mDelta
Tue 12/92:02 pmGCM - MDW
1 stop8h 42mDelta
Deal found 4/17$620
This Southwest deal was found by Cheapflights users on 4/17. 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 7/149:45 pmMDW - GCM
2 stops14h 05mSouthwest
Sat 7/1911:30 amGCM - MDW
1 stop7h 30mSouthwest
Deal found 4/17$706
This Mytrip deal was found by Cheapflights users on 4/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/142:00 pmMDW - GCM
3 stops22h 45mWestJet
Sat 7/191:45 pmGCM - MDW
3 stops23h 17mWestJet
Deal found 4/17$1,490

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 April 17, 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

Sun 6/1

4:06 pm-5:20 pm

1 stop25h 14m

George Town Owen Roberts Intl

Sun 6/8

12:40 pm-10:32 pm

1 stop9h 52m

$617

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 5/17

6:00 am-11:38 am

1 stop5h 38m

George Town Owen Roberts Intl

Wed 5/21

12:35 pm-9:27 pm

1 stop8h 52m

$645

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/14

9:45 pm-11:50 am

2 stops14h 05m

George Town Owen Roberts Intl

Sat 7/19

11:30 am-7:00 pm

1 stop7h 30m

$706

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/14

2:00 pm-12:45 pm

3 stops22h 45m

George Town Owen Roberts Intl

Sat 7/19

1:45 pm-1:02 pm

3 stops23h 17m

$1,490

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 6/1

6:00 am-11:20 am

1 stop5h 20m

$298

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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 April 17, 2025.
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,280 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,917 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,809 reviews
Southwest
8.0
Very good
4,280 reviews

Crew

8.6

Entertainment

7.6

Overall

8.0

Comfort

8.0

Food

7.1

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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.

  • 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.

See more FAQs

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