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$355+ 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 6/9. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
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 April 17, 2025.

Round-trip from

$811
(Delta)

One-way from

$355
(Southwest)

Popular in

March

Cheapest in

September

Average price

$908
From Cayman Islands to Chicago Midway
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One-way flight from Cayman Islands to Chicago Midway
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Highest demand for flights based on searches. 31% potential increase in price ($297 potential increase over avg. RT price).
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Cheapest flight prices on average. 6% potential price decrease ($39 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 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 April 17, 2025.

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.
Thu 5/2912:35 pmGCM - MDW
1 stop8h 52mDelta
Tue 6/36:00 amMDW - GCM
1 stop5h 20mDelta
Deal found 4/17$811

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 April 17, 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

Thu 5/29

12:35 pm-9:27 pm

1 stop8h 52m

Chicago Midway

Tue 6/3

6:00 am-11:20 am

1 stop5h 20m

$811

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 6/9

12:45 pm-11:40 pm

1 stop10h 55m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

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

Rainfall in Midway by month

Plan your trip to Midway by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago Midway Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago Midway Airport when rainfall is around 1.7 in.

Temperature in Midway by month

Plan your trip to Midway by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago Midway Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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

Entertainment

7.6

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.1

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

Entertainment

7.6

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.1

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

Entertainment

7.6

Boarding

8.2

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.1

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 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 the Cayman Islands?

Book flights to the Cayman Islands if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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