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Cheap flights from Midway (MDW) to the Cayman Islands from $164

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 7/16. 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
Jun 11 — Jun 181
From?
To?
Tue 6/11
Tue 6/18
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.

What is the cheapest time of day to fly from MDW to 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 Midway to Cayman Islands flights in June & July 2024

Find cheap flight options from Midway to Cayman Islands specifically for the months of June and July 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,050,429 searches. Prices were last updated on June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in June and July 2024. Check back soon for alternative fares.
Tue 7/96:00 amMDW - GCM
1 stop5h 30mDelta
Wed 7/1712:50 pmGCM - MDW
1 stop8h 56mDelta
Deal found 6/6$478
Tue 7/96:00 amMDW - GCM
1 stop5h 30mDelta
Wed 7/1712:50 pmGCM - MDW
2 stops19h 48mDelta
Deal found 6/6$483
Fri 7/59:31 amMDW - GCM
1 stop11h 49mMultiple Airlines
Fri 7/1211:05 amGCM - MDW
1 stop12h 31mMultiple Airlines
Deal found 6/5$534
Mon 7/18:27 amMDW - GCM
1 stop12h 53mMultiple Airlines
Fri 7/511:05 amGCM - MDW
1 stop12h 31mMultiple Airlines
Deal found 6/5$550
Sat 6/83:14 pmMDW - GCM
2 stops24h 56mMultiple Airlines
Fri 6/144:45 pmGCM - MDW
1 stop15h 49mMultiple Airlines
Deal found 6/5$651
Sat 6/88:00 amMDW - GCM
1 stop28h 44mMultiple Airlines
Fri 6/144:45 pmGCM - MDW
1 stop15h 49mMultiple Airlines
Deal found 6/5$659
Fri 7/51:11 pmMDW - GCM
2 stops23h 28mMultiple Airlines
Fri 7/1211:05 amGCM - MDW
1 stop12h 31mMultiple Airlines
Deal found 6/5$661
Mon 7/18:27 amMDW - GCM
1 stop12h 53mMultiple Airlines
Fri 7/511:05 amGCM - MDW
2 stops9h 02mMultiple Airlines
Deal found 6/5$696
Fri 6/288:27 amMDW - GCM
1 stop12h 53mMultiple Airlines
Mon 7/89:30 amGCM - MDW
2 stops31h 40mMultiple Airlines
Deal found 6/5$731

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 3,050,429 searches. Data last updated June 6, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in June and July 2024. Check back soon for alternative fares.
Sun 11/176:00 amMDW - GCM
1 stop5h 30mDelta
Fri 11/221:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 6/5$418
Tue 12/36:00 amMDW - GCM
1 stop5h 30mDelta
Tue 12/101:55 pmGCM - MDW
2 stops19h 50mDelta
Deal found 6/6$423
Sat 8/178:13 pmMDW - GCM
1 stop15h 17mMultiple Airlines
Sat 8/249:10 amGCM - MDW
1 stop10h 08mMultiple Airlines
Deal found 6/6$440
Fri 9/66:05 pmMDW - GCM
2 stops17h 30mDelta
Fri 9/1312:50 pmGCM - MDW
2 stops19h 50mDelta
Deal found 6/5$448
Tue 9/105:45 pmMDW - GCM
2 stops41h 45mDelta
Sun 9/1512:50 pmGCM - MDW
1 stop8h 48mDelta
Deal found 6/6$458
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
1 stop8h 48mDelta
Deal found 6/6$473
Tue 7/96:00 amMDW - GCM
1 stop5h 30mDelta
Wed 7/1712:50 pmGCM - MDW
1 stop8h 56mDelta
Deal found 6/6$478
Tue 7/96:00 amMDW - GCM
1 stop5h 30mDelta
Wed 7/1712:50 pmGCM - MDW
2 stops19h 48mDelta
Deal found 6/6$483
Sat 8/176:00 amMDW - GCM
1 stop5h 35mDelta
Sat 8/241:00 pmGCM - MDW
1 stop8h 46mDelta
Deal found 6/5$498

One-way flights to Cayman Islands from Midway

Search for one-way flight options from Midway to Cayman Islands. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,050,429 searches. Data last updated June 6, 2024.
Some of the best available deals we've found on one-way flights from Chicago to Cayman Islands. Users needing a return flight from Chicago to Cayman Islands should utilize the search form above.
Tue 7/167:37 pmMDW - GCM
1 stop20h 33mMultiple Airlines
Deal found 6/6$164
Mon 7/159:31 amMDW - GCM
1 stop6h 39mMultiple Airlines
Deal found 6/6$165
Thu 7/182:36 pmMDW - GCM
1 stop21h 04mMultiple Airlines
Deal found 6/6$179
Fri 7/199:31 amMDW - GCM
1 stop11h 49mMultiple Airlines
Deal found 6/6$233
Sat 7/209:31 amMDW - GCM
1 stop25h 59mMultiple Airlines
Deal found 6/6$274
Wed 7/173:36 pmMDW - GCM
2 stops29h 44mMultiple Airlines
Deal found 6/6$303
Sat 11/166:15 pmMDW - GCM
1 stop17h 15mDelta
Deal found 6/5$308
Sat 7/208:48 amMDW - GCM
2 stops31h 22mMultiple Airlines
Deal found 6/6$376
Thu 7/1810:26 amMDW - GCM
2 stops29h 19mMultiple Airlines
Deal found 6/6$388

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 3,050,429 searches. Data last updated June 6, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$418 - $550

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 11/17

1 stop5h 30m

George Town Owen Roberts Intl

Fri 11/22

1 stop8h 49m

$418

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Tue 12/3

1 stop5h 30m

George Town Owen Roberts Intl

Tue 12/10

2 stops19h 50m

$423

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/17

1 stop15h 17m

George Town Owen Roberts Intl

Sat 8/24

1 stop10h 08m

$440

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 9/6

2 stops17h 30m

George Town Owen Roberts Intl

Fri 9/13

2 stops19h 50m

$448

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Tue 9/10

2 stops41h 45m

George Town Owen Roberts Intl

Sun 9/15

1 stop8h 48m

$458

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 48m

$473

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Tue 7/9

1 stop5h 30m

George Town Owen Roberts Intl

Wed 7/17

1 stop8h 56m

$478

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 7/5

1 stop11h 49m

George Town Owen Roberts Intl

Fri 7/12

1 stop12h 31m

$534

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/1

1 stop12h 53m

George Town Owen Roberts Intl

Fri 7/5

1 stop12h 31m

$550

Flights are sorted by cheapest first

Deals found on 6/5

No data available for this route at this time. Please check back soon.

Best time to book a flight from Midway to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Midway 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.

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 June 6, 2024.
Read reviews from past customers who have flown WestJet and Delta from Chicago to Cayman Islands. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

8.0

Food

7.4

Crew

8.6

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
10,368 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

8.0

Food

7.4

Crew

8.6

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
7.5
Good
2,856 reviews
Delta
8.0
Very good
10,368 reviews

Boarding

8.2

Overall

8.0

Comfort

7.9

Entertainment

8.0

Food

7.4

Crew

8.6

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 Delta for just $418, but on average you can expect to pay $541.

  • 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 6/6.

  • What is the cheapest month to book a flight from Chicago Midway Airport to Cayman Islands?

    Currently, August is the cheapest month in which you can book a flight from Chicago Midway Airport to Cayman Islands (average of $445). Flying from Chicago Midway Airport to Cayman Islands in June is currently the most expensive (average of $561). 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

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Alternative routes for Midway to Cayman Islands
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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 3,050,429 searches. Data last updated June 6, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$408Average$628FlexibilityNo 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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