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Cheap flights from Midway (MDW) to the Cayman Islands from $458

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 6/6. 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.
MDW — GCM
May 14 — May 211
From?
To?
Tue 5/14
Tue 5/21
1 adult, Economy
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How far in advance should I book a flight from Chicago Midway Airport to Cayman Islands?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 22 days in advance, which can save you up to 81% on flights from Chicago Midway Airport to Cayman Islands compared to booking the week you need them. Waiting 22 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $671. For sooner than that we have options available in the next 3 days from $671.

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

Flights from Chicago Midway Airport to Cayman Islands lean towards being more expensive in December. Prices are generally better when you fly from Chicago Midway Airport to Cayman Islands in October, with the cheapest ticket starting at $380.

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Cayman Islands as you normally would.

Cheap Delta flights from Midway to Cayman Islands

Explore cheap flight options specifically provided by Delta for the route between Midway and Cayman Islands. 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 2,749,864 searches. Data last updated May 9, 2024.
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/8$603
Thu 6/66:00 amMDW - GCM
1 stop5h 31mDelta
Tue 6/1112:55 pmGCM - MDW
2 stops19h 53mDelta
Deal found 5/9$608
Thu 6/66:00 amMDW - GCM
1 stop5h 31mDelta
Thu 6/1312:55 pmGCM - MDW
2 stops19h 53mDelta
Deal found 5/7$693
Wed 5/296:00 amMDW - GCM
1 stop5h 26mDelta
Thu 5/3012:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/8$748
Wed 5/296:00 amMDW - GCM
1 stop5h 26mDelta
Thu 5/3012:51 pmGCM - MDW
2 stops23h 49mDelta
Deal found 5/8$753
Thu 10/176:50 pmMDW - GCM
1 stop16h 40mDelta
Sun 10/2712:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/8$803
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Sat 6/112:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/8$818
Sat 6/296:00 amMDW - GCM
1 stop5h 36mDelta
Sat 7/61:01 pmGCM - MDW
1 stop8h 45mDelta
Deal found 5/8$833
Fri 5/176:48 pmMDW - GCM
1 stop16h 38mDelta
Mon 5/2012:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/8$1,220

Cheap Midway to Cayman Islands flights in May & June 2024

Find cheap flight options from Midway to Cayman Islands specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Prices were last updated on May 9, 2024.
Thu 6/62:36 pmMDW - GCM
1 stop21h 04mMultiple Airlines
Tue 6/1111:30 amGCM - MDW
1 stop20h 01mMultiple Airlines
Deal found 5/9$458
Thu 6/62:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Thu 6/134:45 pmGCM - MDW
1 stop14h 46mMultiple Airlines
Deal found 5/7$474
Sun 5/267:23 pmMDW - GCM
1 stop20h 47mMultiple Airlines
Sun 6/21:50 pmGCM - MDW
1 stop20h 17mMultiple Airlines
Deal found 5/8$560
Thu 6/66:00 amMDW - GCM
1 stop5h 31mDelta
Tue 6/1112:55 pmGCM - MDW
2 stops19h 53mDelta
Deal found 5/9$608
Thu 6/66:00 amMDW - GCM
1 stop5h 31mDelta
Thu 6/1312:55 pmGCM - MDW
2 stops19h 53mDelta
Deal found 5/7$693
Wed 5/296:00 amMDW - GCM
1 stop5h 26mDelta
Thu 5/3012:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/8$748
Wed 5/296:00 amMDW - GCM
1 stop5h 26mDelta
Thu 5/3012:51 pmGCM - MDW
2 stops23h 49mDelta
Deal found 5/8$753
Sun 5/266:00 amMDW - GCM
1 stop5h 26mDelta
Sat 6/112:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/8$818
Sat 6/296:00 amMDW - GCM
1 stop5h 36mDelta
Sat 7/61:01 pmGCM - MDW
1 stop8h 45mDelta
Deal found 5/8$833

Midway to Cayman Islands 2024 flight deals

Discover exclusive flight deals for travel between Midway and Cayman Islands in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 9, 2024.
Thu 6/62:36 pmMDW - GCM
1 stop21h 04mMultiple Airlines
Tue 6/1111:30 amGCM - MDW
1 stop20h 01mMultiple Airlines
Deal found 5/9$458
Thu 6/62:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Thu 6/134:45 pmGCM - MDW
1 stop14h 46mMultiple Airlines
Deal found 5/7$474
Sun 5/267:23 pmMDW - GCM
1 stop20h 47mMultiple Airlines
Sun 6/21:50 pmGCM - MDW
1 stop20h 17mMultiple Airlines
Deal found 5/8$560
Wed 12/111:10 pmMDW - GCM
2 stops22h 20mDelta
Fri 12/201:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 5/7$583
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/8$603
Wed 12/111:10 pmMDW - GCM
2 stops22h 20mDelta
Sun 12/221:56 pmGCM - MDW
1 stop9h 13mDelta
Deal found 5/7$608
Mon 12/166:50 pmMDW - GCM
1 stop16h 40mDelta
Fri 12/273:55 pmGCM - MDW
1 stop7h 14mDelta
Deal found 5/7$630
Thu 6/66:00 amMDW - GCM
1 stop5h 31mDelta
Thu 6/1312:55 pmGCM - MDW
2 stops19h 53mDelta
Deal found 5/7$693
Mon 12/166:00 amMDW - GCM
1 stop5h 30mDelta
Sat 12/213:55 pmGCM - MDW
1 stop7h 14mDelta
Deal found 5/7$728

Midway to Cayman Islands flights leaving soon

Find last-minute flight options from Midway to Cayman Islands 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 2,749,864 searches. Data last updated May 9, 2024.
Fri 5/176:48 pmMDW - GCM
1 stop16h 38mDelta
Mon 5/2012:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/8$1,220

Find flights from Midway to Cayman Islands within your budget

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 2,749,864 searches. Data last updated May 9, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$458 - $803

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/6

1 stop21h 04m

George Town Owen Roberts Intl

Tue 6/11

1 stop20h 01m

$458

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/6

1 stop6h 44m

George Town Owen Roberts Intl

Thu 6/13

1 stop14h 46m

$474

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 5/26

1 stop20h 47m

George Town Owen Roberts Intl

Sun 6/2

1 stop20h 17m

$560

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 9/6

1 stop5h 30m

George Town Owen Roberts Intl

Fri 9/13

1 stop8h 54m

$603

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/6

1 stop5h 31m

George Town Owen Roberts Intl

Tue 6/11

2 stops19h 53m

$608

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/6

1 stop5h 31m

George Town Owen Roberts Intl

Thu 6/13

2 stops19h 53m

$693

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Wed 5/29

1 stop5h 26m

George Town Owen Roberts Intl

Thu 5/30

1 stop9h 10m

$748

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Wed 5/29

1 stop5h 26m

George Town Owen Roberts Intl

Thu 5/30

2 stops23h 49m

$753

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 10/17

1 stop16h 40m

George Town Owen Roberts Intl

Sun 10/27

1 stop8h 54m

$803

Flights are sorted by cheapest first

Deals found on 5/9

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 May 9, 2024.
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

Delta
8.0
Very good
10,778 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

WestJet
7.6
Good
2,942 reviews
Delta
8.0
Very good
10,778 reviews
Check prices

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Food

7.4

Reviews

1 / 10

Bad experience with the staff boarding the gate. I couldn’t board with my carry on, personal item and a funny bag. I had to put my passport inside my pockets and put the funny bag inside the personal item. Then after passing the staff pull out everything again.

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 flights from Chicago Midway Airport to Cayman Islands for under $500 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Cayman Islands for under $500. The cheapest flight booked recently is on Multiple Airlines for just $458, but on average you can expect to pay $918.

  • Are there last-minute flights available from Chicago Midway Airport to Cayman Islands for under $1,300?

    There are currently 1+ open flights from Chicago Midway Airport to Cayman Islands within the next 7 days for less than $1,300.

  • What does MDW to GCM mean?

    These are just IATA (International Air Transport Association) codes. They are used in aviation to identify and differentiate airports. That’s why a Chicago Midway Airport to George Town Owen Roberts Intl Airport flight would often be abbreviated as a MDW to GCM flight. Cayman Brac Gerrard-Smith Airport (CYB), Little Cayman Airport (LYB) are some additional IATA codes for airports related to your trip.

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

    The amount of baggage you can bring on your Midway to Cayman Islands 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 Midway to Cayman Islands with specific airlines?

    Yes, Cheapflights allows you to browse and filter Midway to Cayman Islands 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 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.

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

    Many airlines flying from Midway to Cayman Islands 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 Midway to Cayman Islands?

    Yes, you can often find last-minute deals on Midway to Cayman Islands 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 Chicago Midway Airport to Cayman Islands flight deals updated?

    The Chicago Midway Airport to Cayman Islands flight deals you see on this page were last updated on 5/9.

See more FAQs

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Alternative routes for Midway to Cayman Islands
See prices for flight routes from nearby airports that may be better suited for you.

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Top airline flying from Midway to Cayman Islands

Discover the top airline that operate flights from Midway to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,749,864 searches. Data last updated May 9, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$408Average$635FlexibilityNo cancel feeOn-timeN/A
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Search flights from Midway to Cayman Islands by cabin class

Find flights from Midway to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
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Business Class
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Fly with Cheapflights

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

Cheapflights makes it easy to find Midway to Cayman Islands flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

Millions of users choose and trust Cheapflights to book the best flight deals from Midway to Cayman Islands for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

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

Need flexible booking options for your flight to Cayman Islands from Midway? 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 Midway to Cayman Islands become cheaper?

Yes, Cheapflights offers price alerts on Midway to Cayman Islands flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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