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Cheap flights from Midway (MDW) to the Cayman Islands from $158

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 6/25. 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 20 — May 271
From?
To?
Mon 5/20
Mon 5/27
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 2,644,845 searches. Data last updated May 15, 2024.
Find some of the cheapest Delta flights traveling from Chicago to Cayman Islands. Make sure to double check the flight details before booking.
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/15$603
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/15$608
Tue 9/105:59 pmMDW - GCM
2 stops41h 31mDelta
Sun 9/1512:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/15$619
Sun 9/86:00 amMDW - GCM
1 stop5h 30mDelta
Sun 9/1512:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/13$621
Thu 9/56:00 amMDW - GCM
1 stop5h 30mDelta
Mon 9/912:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/14$628
Tue 9/105:59 pmMDW - GCM
2 stops41h 31mDelta
Sun 9/1512:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/15$632
Sat 9/76:00 amMDW - GCM
1 stop5h 30mDelta
Sat 9/1412:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/13$633
Sun 7/286:00 amMDW - GCM
1 stop5h 30mDelta
Fri 8/212:50 pmGCM - MDW
2 stops19h 48mDelta
Deal found 5/14$663
Sun 7/146:55 pmMDW - GCM
1 stop16h 35mDelta
Sat 7/201:00 pmGCM - MDW
1 stop8h 46mDelta
Deal found 5/14$728

Cheap WestJet flights from Midway to Cayman Islands

Explore cheap flight options specifically provided by WestJet 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 2,644,845 searches. Data last updated May 15, 2024.
Browse through some of the cheapest WestJet flights traveling from Chicago to Cayman Islands. Ensure the flight price, dates, time, and airline match your criteria before you book.
Sat 6/2912:45 pmMDW - GCM
2 stops23h 54mWestJet
Sat 7/61:45 pmGCM - MDW
2 stops25h 10mWestJet
Deal found 5/15$2,977
Sat 6/2910:41 amMDW - GCM
2 stops25h 58mWestJet
Sat 7/61:45 pmGCM - MDW
2 stops25h 10mWestJet
Deal found 5/14$2,978
Sun 8/256:45 pmMDW - GCM
2 stops41h 54mWestJet
Sun 9/11:45 pmGCM - MDW
2 stops25h 12mWestJet
Deal found 5/14$2,994
Fri 6/147:19 pmMDW - GCM
2 stops41h 20mWestJet
Sat 6/221:45 pmGCM - MDW
2 stops23h 59mWestJet
Deal found 5/15$3,029

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 2,644,845 searches. Prices were last updated on May 15, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in May and June 2024. Check back soon for alternative fares.
Thu 6/132:36 pmMDW - GCM
1 stop21h 04mMultiple Airlines
Sun 6/162:00 pmGCM - MDW
1 stop7h 46mMultiple Airlines
Deal found 5/14$553
Thu 6/132:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Sun 6/162:00 pmGCM - MDW
2 stops23h 38mMultiple Airlines
Deal found 5/14$560
Thu 6/272:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Sun 6/3011:30 amGCM - MDW
1 stop12h 54mMultiple Airlines
Deal found 5/14$622
Thu 6/272:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Sun 6/302:00 pmGCM - MDW
2 stops23h 38mMultiple Airlines
Deal found 5/14$659
Sat 6/296:00 amMDW - GCM
1 stop5h 36mDelta
Sat 7/61:01 pmGCM - MDW
1 stop8h 45mDelta
Deal found 5/15$768
Fri 5/2412:04 pmMDW - GCM
2 stops9h 16mMultiple Airlines
Sat 6/111:30 amGCM - MDW
1 stop12h 39mMultiple Airlines
Deal found 5/13$786
Wed 5/296:00 amMDW - GCM
1 stop5h 26mDelta
Thu 5/3012:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/13$838
Wed 5/296:00 amMDW - GCM
1 stop5h 26mDelta
Thu 5/3012:51 pmGCM - MDW
2 stops23h 49mDelta
Deal found 5/13$843
Fri 5/176:00 amMDW - GCM
1 stop5h 26mDelta
Mon 5/2012:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/14$1,058

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 2,644,845 searches. Data last updated May 15, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in May and June 2024. Check back soon for alternative fares.
Fri 7/198:13 pmMDW - GCM
1 stop19h 57mMultiple Airlines
Wed 7/2411:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 5/14$482
Sun 7/288:13 pmMDW - GCM
1 stop19h 57mMultiple Airlines
Fri 8/211:05 amGCM - MDW
1 stop26h 57mMultiple Airlines
Deal found 5/14$548
Thu 6/132:36 pmMDW - GCM
1 stop21h 04mMultiple Airlines
Sun 6/162:00 pmGCM - MDW
1 stop7h 46mMultiple Airlines
Deal found 5/14$553
Thu 6/132:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Sun 6/162:00 pmGCM - MDW
2 stops23h 38mMultiple Airlines
Deal found 5/14$560
Fri 7/1912:15 pmMDW - GCM
2 stops9h 05mMultiple Airlines
Wed 7/2411:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 5/14$584
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/14$603
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/15$608
Thu 9/55:54 amMDW - GCM
2 stops12h 46mMultiple Airlines
Mon 9/99:30 amGCM - MDW
1 stop9h 48mMultiple Airlines
Deal found 5/14$617
Tue 9/105:59 pmMDW - GCM
2 stops41h 31mDelta
Sun 9/1512:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/15$619

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 2,644,845 searches. Data last updated May 15, 2024.
Have a look at some of the last-minute flights available departing from Chicago to Cayman Islands. To prevent any unwanted surprises, users should verify their flight info before booking.
Fri 5/2412:04 pmMDW - GCM
2 stops9h 16mMultiple Airlines
Sat 6/111:30 amGCM - MDW
1 stop12h 39mMultiple Airlines
Deal found 5/13$786
Fri 5/246:48 pmMDW - GCM
1 stop16h 38mDelta
Sat 6/112:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/13$1,395
Fri 5/246:48 pmMDW - GCM
1 stop16h 38mDelta
Fri 5/3112:51 pmGCM - MDW
1 stop9h 10mDelta
Deal found 5/15$1,510

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 2,644,845 searches. Data last updated May 15, 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 6/257:36 pmMDW - GCM
1 stop20h 34mMultiple Airlines
Deal found 5/15$158
Wed 6/268:27 amMDW - GCM
1 stop7h 43mMultiple Airlines
Deal found 5/15$173
Thu 6/272:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Deal found 5/15$229
Tue 6/2510:16 pmMDW - GCM
3 stops20h 44mMultiple Airlines
Deal found 5/15$606

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 2,644,845 searches. Data last updated May 15, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$482 - $621

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 7/19

1 stop19h 57m

George Town Owen Roberts Intl

Wed 7/24

1 stop7h 48m

$482

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Tue 6/11

1 stop20h 34m

George Town Owen Roberts Intl

Sun 6/16

1 stop17h 31m

$484

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 7/28

1 stop19h 57m

George Town Owen Roberts Intl

Fri 8/2

1 stop26h 57m

$548

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/13

1 stop21h 04m

George Town Owen Roberts Intl

Sun 6/16

1 stop7h 46m

$553

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/13

1 stop6h 44m

George Town Owen Roberts Intl

Sun 6/16

2 stops23h 38m

$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

Fri 9/6

1 stop5h 30m

George Town Owen Roberts Intl

Fri 9/13

2 stops19h 55m

$608

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Tue 9/10

2 stops41h 31m

George Town Owen Roberts Intl

Sun 9/15

1 stop8h 54m

$619

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 9/8

1 stop5h 30m

George Town Owen Roberts Intl

Sun 9/15

2 stops19h 55m

$621

Flights are sorted by cheapest first

Deals found on 5/14

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 15, 2024.
Read reviews from past customers who have flown Delta and WestJet 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
10,691 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Entertainment

8.0

Comfort

7.9

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
10,691 reviews
Delta
8.0
Very good
10,691 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Entertainment

8.0

Comfort

7.9

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
2,920 reviews
Delta
8.0
Very good
10,691 reviews
Check prices

Crew

8.6

Food

7.4

Overall

8.0

Boarding

8.2

Entertainment

8.0

Comfort

7.9

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 $482, but on average you can expect to pay $603.

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

    There are currently 3+ open flights from Chicago Midway Airport to Cayman Islands within the next 7 days for less than $800.

  • 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 5/15.

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 2,644,845 searches. Data last updated May 15, 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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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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