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$382+ Cheap flights from the Cayman Islands to Midway (MDW)

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 9/28. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheap flight deals from Cayman Islands to Midway

Keep the following information in mind while searching for Cayman Islands to Midway flight deals. Data was last updated July 30, 2025.

Round-trip from

$468
(Delta)

One-way from

$382
(Delta)
From Cayman Islands to Chicago Midway
Search Deals
One-way flight from Cayman Islands to Chicago Midway
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Find flight deals from Cayman Islands to Midway

Cheapest flights from Cayman Islands to Midway
Explore the most affordable flight options available from Cayman Islands to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. 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.
Fri 9/1212:52 pmGCM - MDW
1 stop8h 44mDelta
Fri 9/196:00 amMDW - GCM
1 stop5h 36mDelta
Deal found 7/29$468
This Southwest deal was found by Cheapflights users on 7/30. 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.
Fri 11/141:30 pmGCM - MDW
2 stops11h 00mSouthwest
Sun 11/166:05 pmMDW - GCM
2 stops17h 30mSouthwest
Deal found 7/30$500
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Thu 7/3112:40 pmGCM - MDW
1 stop9h 44mMultiple Airlines
Thu 8/72:55 pmMDW - GCM
2 stops25h 05mMultiple Airlines
Deal found 7/30$1,052
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/121:45 pmGCM - MDW
2 stops23h 18mWestJet
Fri 8/151:43 pmMDW - GCM
2 stops23h 02mWestJet
Deal found 7/28$1,433

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Midway 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 July 30, 2025.
Use the filters below to find and compare flights from the Cayman Islands to Chicago Midway Airport that are best for you.

Fly from

Cayman Islands

Fly to

Midway

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 9/12

12:52 pm-9:36 pm

1 stop8h 44m

Chicago Midway

Fri 9/19

6:00 am-11:36 am

1 stop5h 36m

$468

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 11/14

1:30 pm-11:30 pm

2 stops11h 00m

Chicago Midway

Sun 11/16

6:05 pm-12:35 pm

2 stops17h 30m

$500

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 8/12

1:45 pm-1:03 pm

2 stops23h 18m

Chicago Midway

Fri 8/15

1:43 pm-12:45 pm

2 stops23h 02m

$1,433

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 9/28

12:52 pm-9:36 pm

1 stop8h 44m

$382

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 11/29

11:25 am-1:37 pm

1 stop27h 12m

$741

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 1/3

2:20 pm-9:35 pm

2 stops8h 15m

$1,015

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Cayman Islands to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Cayman Islands 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 the Cayman Islands to Chicago Midway Airport
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. 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 Midway. Reviews last updated July 30, 2025.
Get a feel of what it's like to fly with Delta and WestJet from the Cayman Islands to Chicago Midway Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
Delta
8.0
Very good
7,980 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.
WestJet
7.2
Good
2,975 reviews
Delta
8.0
Very good
7,980 reviews

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Comfort

7.9

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Michael,Jul 2025

AMS - ATL

Overall it was great experience, with the exception of snack food. The food offered in two main meals was just fine but for the mid-flight snack, the only option was a large cookie, too sweet and high sugar content. Snacks at the back of the plane were also mainly sweets. There was one nice baked cheddar option but it quickly ran out.

Related info for your journey

Find useful and relevant information for your journey from Cayman Islands to Midway. 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 Cayman Islands to Midway that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Cayman Islands to Midway 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 Cayman Islands to Chicago Midway Airport?

    Currently, April is the cheapest month in which you can book a flight from Cayman Islands to Chicago Midway Airport (average of $160). Flying from Cayman Islands to Chicago Midway Airport in November is currently the most expensive (average of $249). 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

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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