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Cheap flights from Midway (MDW) to the Cayman Islands from $303

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 11/16. 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
may. 27 — jun. 31
From?
To?
lun. 5/27
lun. 6/3
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 2,730,072 searches. Data last updated mayo 22, 2024.
Find some of the cheapest Delta flights traveling from Chicago to Cayman Islands. Make sure to double check the flight details before booking.
dom. 9/226:00 amMDW - GCM
1 stop5h 30mDelta
lun. 9/2312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$346
jue. 9/199:35 amMDW - GCM
2 stops25h 55mDelta
dom. 9/2912:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$351
sáb. 9/216:15 pmMDW - GCM
1 stop17h 15mDelta
jue. 9/2612:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$354
mar. 9/105:59 pmMDW - GCM
2 stops41h 31mDelta
dom. 9/1512:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$361
lun. 9/236:00 amMDW - GCM
1 stop5h 30mDelta
sáb. 9/2812:50 pmGCM - MDW
2 stops23h 41mDelta
Deal found 5/22$364
vie. 9/66:00 amMDW - GCM
1 stop5h 30mDelta
vie. 9/1312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/21$443
vie. 9/66:00 amMDW - GCM
1 stop5h 30mDelta
vie. 9/1312:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/21$448
mar. 9/105:59 pmMDW - GCM
2 stops41h 31mDelta
dom. 9/1512:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/21$458
mar. 9/105:59 pmMDW - GCM
2 stops41h 31mDelta
dom. 9/1512:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/22$511

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 2,730,072 searches. Data last updated mayo 22, 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.
sáb. 6/2910:41 amMDW - GCM
2 stops25h 58mWestJet
sáb. 7/61:45 pmGCM - MDW
2 stops23h 59mWestJet
Deal found 5/22$3,669
sáb. 6/2910:41 amMDW - GCM
2 stops25h 58mWestJet
sáb. 7/61:45 pmGCM - MDW
2 stops25h 10mWestJet
Deal found 5/21$3,670

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 2,730,072 searches. Prices were last updated on mayo 22, 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.
vie. 6/288:27 amMDW - GCM
1 stop12h 53mMultiple Airlines
dom. 7/72:00 pmGCM - MDW
1 stop18h 36mMultiple Airlines
Deal found 5/21$624
sáb. 6/299:31 amMDW - GCM
1 stop6h 39mMultiple Airlines
dom. 7/72:00 pmGCM - MDW
1 stop18h 36mMultiple Airlines
Deal found 5/21$658
sáb. 6/16:00 amMDW - GCM
1 stop5h 26mDelta
sáb. 6/81:01 pmGCM - MDW
1 stop8h 47mDelta
Deal found 5/20$738
sáb. 6/296:00 amMDW - GCM
1 stop5h 36mDelta
sáb. 7/61:01 pmGCM - MDW
1 stop8h 45mDelta
Deal found 5/21$913
mié. 6/56:00 amMDW - GCM
1 stop5h 31mDelta
dom. 6/1612:55 pmGCM - MDW
1 stop8h 51mDelta
Deal found 5/21$922
mié. 6/56:00 amMDW - GCM
1 stop5h 31mDelta
dom. 6/1612:55 pmGCM - MDW
2 stops19h 53mDelta
Deal found 5/21$927
mié. 5/227:23 pmMDW - GCM
1 stop25h 57mMultiple Airlines
sáb. 5/2511:30 amGCM - MDW
1 stop12h 39mMultiple Airlines
Deal found 5/21$971
mié. 5/227:23 pmMDW - GCM
1 stop25h 57mMultiple Airlines
sáb. 5/259:10 amGCM - MDW
2 stops11h 56mMultiple Airlines
Deal found 5/21$972
sáb. 6/296:00 amMDW - GCM
1 stop5h 36mDelta
sáb. 7/61:01 pmGCM - MDW
1 stop8h 45mDelta
Deal found 5/22$978

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 2,730,072 searches. Data last updated mayo 22, 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.
dom. 9/226:00 amMDW - GCM
1 stop5h 30mDelta
sáb. 9/2812:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$346
jue. 9/195:59 pmMDW - GCM
2 stops17h 31mDelta
jue. 9/2612:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$351
sáb. 9/216:15 pmMDW - GCM
1 stop17h 15mDelta
jue. 9/2612:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$354
mar. 9/105:59 pmMDW - GCM
2 stops41h 31mDelta
dom. 9/1512:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/22$361
lun. 9/236:00 amMDW - GCM
1 stop5h 30mDelta
sáb. 9/2812:50 pmGCM - MDW
2 stops23h 41mDelta
Deal found 5/22$364
lun. 12/26:00 amMDW - GCM
1 stop5h 30mDelta
vie. 12/61:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 5/21$418
lun. 12/26:00 amMDW - GCM
1 stop5h 30mDelta
vie. 12/61:55 pmGCM - MDW
2 stops19h 50mDelta
Deal found 5/21$423
vie. 9/66:00 amMDW - GCM
1 stop5h 30mDelta
vie. 9/1312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 5/21$443
vie. 9/66:00 amMDW - GCM
1 stop5h 30mDelta
vie. 9/1312:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 5/21$448

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 2,730,072 searches. Data last updated mayo 22, 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.
sáb. 6/16:00 amMDW - GCM
1 stop5h 26mDelta
sáb. 6/81:01 pmGCM - MDW
1 stop8h 47mDelta
Deal found 5/20$738

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 2,730,072 searches. Data last updated mayo 22, 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.
sáb. 11/166:15 pmMDW - GCM
1 stop17h 15mDelta
Deal found 5/21$303
mar. 7/166:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/22$662
vie. 7/196:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/22$692
mié. 7/176:00 amMDW - GCM
1 stop5h 30mDelta
Deal found 5/22$702
jue. 7/186:55 pmMDW - GCM
1 stop16h 35mDelta
Deal found 5/22$827
sáb. 11/165:00 pmMDW - GCM
2 stops19h 35mWestJet
Deal found 5/21$1,435

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 2,730,072 searches. Data last updated mayo 22, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$346 - $518

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

dom. 9/22

1 stop5h 30m

George Town Owen Roberts Intl

lun. 9/23

1 stop8h 54m

$346

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

jue. 9/19

2 stops25h 55m

George Town Owen Roberts Intl

dom. 9/29

1 stop8h 54m

$351

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

sáb. 9/21

1 stop17h 15m

George Town Owen Roberts Intl

jue. 9/26

1 stop8h 54m

$354

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

mar. 9/10

2 stops41h 31m

George Town Owen Roberts Intl

dom. 9/15

1 stop8h 54m

$361

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

lun. 9/23

1 stop5h 30m

George Town Owen Roberts Intl

sáb. 9/28

2 stops23h 41m

$364

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

vie. 9/6

1 stop5h 30m

George Town Owen Roberts Intl

vie. 9/13

1 stop8h 54m

$443

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

sáb. 9/21

1 stop8h 22m

George Town Owen Roberts Intl

mié. 9/25

1 stop7h 48m

$505

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

jue. 7/11

1 stop6h 44m

George Town Owen Roberts Intl

dom. 7/14

1 stop18h 36m

$509

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

lun. 9/23

1 stop6h 06m

George Town Owen Roberts Intl

mié. 9/25

1 stop7h 48m

$518

Flights are sorted by cheapest first

Deals found on 5/22

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 mayo 22, 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
10,585 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

8.0

Boarding

8.2

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
10,585 reviews
Delta
8.0
Very good
10,585 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

8.0

Boarding

8.2

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
2,898 reviews
Delta
8.0
Very good
10,585 reviews
Check prices

Overall

8.0

Comfort

7.9

Entertainment

8.0

Boarding

8.2

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 $400 on Cheapflights?

    Yes, there are multiple flights from Chicago Midway Airport to Cayman Islands for under $400. The cheapest flight booked recently is on Delta for just $346, but on average you can expect to pay $495.

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

    There are currently 1+ 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 5/22.

  • When is the best time 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 $442). Flying from Chicago Midway Airport to Cayman Islands in June is currently the most expensive (average of $560). 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
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 2,730,072 searches. Data last updated mayo 22, 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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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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