HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Midway

$600+ Cheap flights from the Cayman Islands to Midway (MDW)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/20. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — MDW
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cayman Islands to Midway with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 February 20, 2025.

Round-trip from

$600
(Southwest)

Popular in

March

Cheapest in

September
From Cayman Islands to Chicago Midway
Search Deals
Highest demand for flights based on searches. 33% potential increase in price ($325 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 7% potential price decrease ($45 potential savings vs. average RT price).
Search Deals

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 February 20, 2025.

This Southwest deal was found by Cheapflights users on 2/19. 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 3/2012:40 pmGCM - MDW
1 stop7h 25mSouthwest
Wed 3/266:30 pmMDW - GCM
2 stops17h 15mSouthwest
Deal found 2/19$600
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Sat 4/511:25 amGCM - MDW
1 stop11h 11mMultiple Airlines
Sat 4/124:10 pmMDW - GCM
1 stop24h 00mMultiple Airlines
Deal found 2/18$619

Find flights from Cayman Islands to Midway within your budget

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 February 20, 2025.

Fly from

Cayman Islands

Fly to

Midway

Route

Depart

Return

Price

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 3/20

12:40 pm-8:05 pm

1 stop7h 25m

Chicago Midway

Wed 3/26

6:30 pm-11:45 am

2 stops17h 15m

$600

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 4/5

11:25 am-10:36 pm

1 stop11h 11m

Chicago Midway

Sat 4/12

4:10 pm-4:10 pm

1 stop24h 00m

$619

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

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.

Travel insights for flights from Cayman Islands to Midway

Get recent, data-driven insights about flights from Cayman Islands to Midway including ideal travel times, pricing trends, and more.

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 February 20, 2025.
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Food

7.1

Crew

8.7

Entertainment

7.6

Boarding

8.2

Comfort

8.1

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Cayman Islands to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Punta Cana to O'Hare Intl flights
Santo Domingo to O'Hare Intl flights
Nassau to Midway flights
Santo Domingo to Midway flights
Punta Cana to Midway flights
Port of Spain to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
George Town to O'Hare Intl flights
Montego Bay to Midway flights
Simpson Bay to O'Hare Intl flights
Kingston to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to Midway flights
Aguadilla to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Aguadilla to Midway flights
Port Au Prince to O'Hare Intl flights
Port Au Prince to Midway flights
St. John's to O'Hare Intl flights
Vieques to O'Hare Intl flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.