HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news

Cheap flights from the Cayman Islands to Midway (MDW) from $614

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 8/2. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
GCM — MDW
may. 21 — may. 281
From?
To?
mar. 5/21
mar. 5/28
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

What is the cheapest month to fly from Cayman Islands to Chicago Midway Airport?

November can be a great time to fly to Chicago Midway Airport from Cayman Islands with a flight ticket averaging about $586. Cheapflights users have found deals in the month of November for as cheap as $373. The most expensive prices can be found in the month of March.

When is the cheapest time to fly from Cayman Islands to Chicago Midway Airport (KY - MDW)?

When flying from Cayman Islands to Chicago Midway Airport, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Cheap Delta flights from Cayman Islands to Midway

Explore cheap flight options specifically provided by Delta for the route between Cayman Islands and Midway. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated mayo 16, 2024.
vie. 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
lun. 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/16$614
vie. 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
lun. 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/15$674
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$796
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$848
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$861
jue. 5/2312:51 pmGCM - MDW
2 stops44h 00mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/15$927
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/14$984

Cheap Cayman Islands to Midway flights in May & June 2024

Find cheap flight options from Cayman Islands to Midway specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Prices were last updated on mayo 16, 2024.
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$796
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$848
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$861
jue. 5/2312:51 pmGCM - MDW
2 stops44h 00mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/15$927
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/14$984
vie. 5/1712:51 pmGCM - MDW
1 stop9h 10mDelta
mié. 5/226:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$1,321

Cayman Islands to Midway 2024 flight deals

Discover exclusive flight deals for travel between Cayman Islands and Midway in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated mayo 16, 2024.
vie. 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
lun. 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/16$614
vie. 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
lun. 8/56:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/15$674
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$796
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$848
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$861
jue. 5/2312:51 pmGCM - MDW
2 stops44h 00mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/15$927
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/14$984
vie. 5/1712:51 pmGCM - MDW
1 stop9h 10mDelta
mié. 5/226:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$1,321

Cayman Islands to Midway flights leaving soon

Find last-minute flight options from Cayman Islands to Midway for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,637,452 searches. Data last updated mayo 16, 2024.
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$783
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/15$796
jue. 5/2312:51 pmGCM - MDW
1 stop9h 10mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$848
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Deal found 5/14$861
jue. 5/2312:51 pmGCM - MDW
2 stops44h 00mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/15$927
jue. 5/2312:51 pmGCM - MDW
2 stops28h 15mDelta
dom. 5/269:32 amMDW - GCM
2 stops49h 54mDelta
Deal found 5/14$984

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 2,637,452 searches. Data last updated mayo 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$614 - $674

Route

Depart

Return

Price

George Town Owen Roberts IntlChicago Midway

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 8/2

2 stops19h 48m

Chicago Midway

lun. 8/5

1 stop5h 30m

$614

George Town Owen Roberts IntlChicago Midway

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

vie. 8/2

2 stops19h 48m

Chicago Midway

lun. 8/5

1 stop5h 30m

$674

Flights are sorted by cheapest first

Deals found on 5/16

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 mayo 16, 2024.
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Delta
8.0
Very good
10,673 reviews
Delta
8.0
Very good
10,673 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Comfort

7.9

Entertainment

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

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 flights from Cayman Islands to Chicago Midway Airport for under $700 on Cheapflights?

    Yes, there are multiple flights from Cayman Islands to Chicago Midway Airport for under $700. The cheapest flight booked recently is on Delta for just $614, but on average you can expect to pay $644.

  • Are there last-minute flights available from Cayman Islands to Chicago Midway Airport for under $800?

    There are currently 6+ open flights from Cayman Islands to Chicago Midway Airport within the next 7 days for less than $800.

  • What does GCM to MDW mean?

    GCM and MDW are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. GCM to MDW refers to a flight route from George Town Owen Roberts Intl Airport to Chicago Midway Airport. Cayman Brac Gerrard-Smith Airport (CYB), Little Cayman Airport (LYB) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Cayman Islands to Midway that include extra baggage allowance?

    The amount of baggage you can bring on your Cayman Islands to Midway flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Cayman Islands to Midway with specific airlines?

    Yes, Cheapflights allows you to browse and filter Cayman Islands to Midway flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Cayman Islands to Midway that allow pets onboard?

    Many airlines flying from Cayman Islands to Midway offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Cayman Islands to Midway?

    Yes, you can often find last-minute deals on Cayman Islands to Midway flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Cayman Islands to Chicago Midway Airport flight deals updated?

    The Cayman Islands to Chicago Midway Airport flight deals you see on this page were last updated on 5/16.

See more FAQs

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
Santo Domingo to O'Hare Intl flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Punta Cana to O'Hare Intl flights
Nassau to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Punta Cana to Midway flights
Montego Bay to Midway flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
George Town to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
Nassau to Midway flights
Saint Thomas Island to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Aguadilla to Midway flights
Port Au Prince to Midway flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Roseau to O'Hare Intl flights
Culebra to O'Hare Intl flights
Simpson Bay to Midway flights
St. John's to O'Hare Intl flights
Vieques to O'Hare Intl flights
Oakland, California to San Diego flights
USA to Amsterdam flights
New York to Atlanta flights
Hawaii to Japan flights
Detroit to Chicago flights
Fort Lauderdale to Los Angeles flights
Dallas to Orlando flights
Dallas to Dubai flights
Long Beach to Las Vegas flights
Houston to Atlanta flights
Tampa to Seattle flights
Cayman Islands to Manchester, New Hampshire flights

Search flights from Cayman Islands to Midway by cabin class

Find flights from Cayman Islands to Midway, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Prem Econ Class
Economy Class

Book a flight to one of these trending destinations

User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
Flights to Montes Claros
Flights to Girona Costa Brava
Flights to Naxos
Flights to Bourgas
Flights to Hyannis Barnstable
Flights to Samos
Flights to Reggio Calabria Tito Menniti
Flights to Devils Lake
Flights to Ningbo Lishe Intl
Flights to Pellston Emmet County
Flights to Provincetown
Flights to Cortez Montezuma County
Flights to Ohrid
Flights to Oran Es Senia
Flights to Menorca/Mahon
Flights to Hakodate
Flights to Ordu/Giresun
Flights to Laayoune Hassan I
Flights to Cornwall Newquay
Flights to Melilla
Flights to Rennes St Jacques
Flights to Parikia Paros
Flights to Constanţa Mihail Kogalniceanu
Flights to Miyakojima Hirara

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Cayman Islands to Midway?

When you search for this flight from Cayman Islands to Midway, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.

Why should you use Cheapflights to find cheap flight tickets from Cayman Islands to Midway?

Cheapflights helps you find that perfect flight to Midway from Cayman Islands by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Cayman Islands to Midway with no change fees?

Need flexible booking options for your flight to Midway from Cayman Islands? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Cayman Islands to Midway become cheaper?

Yes! Start tracking prices for Cayman Islands to Midway flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.

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.
View all available airlines