Cheap flights from Midway (MDW) to the Cayman Islands from $313

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
Jun 18 — Jun 251

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 3,214,720 searches. Prices were last updated on June 13, 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.
Thu 7/42:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Tue 7/911:30 amGCM - MDW
1 stop21h 06mMultiple Airlines
Deal found 6/11$511
Wed 7/249:31 amMDW - GCM
1 stop6h 39mMultiple Airlines
Sun 7/282:00 pmGCM - MDW
1 stop18h 36mMultiple Airlines
Deal found 6/11$538
Thu 6/272:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Sun 6/3011:30 amGCM - MDW
1 stop12h 54mMultiple Airlines
Deal found 6/12$575
Thu 6/272:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Fri 6/2811:05 amGCM - MDW
1 stop12h 32mMultiple Airlines
Deal found 6/12$591
Thu 6/272:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Mon 7/12:00 pmGCM - MDW
1 stop9h 39mMultiple Airlines
Deal found 6/12$594
Thu 7/48:51 pmMDW - GCM
2 stops39h 48mMultiple Airlines
Tue 7/911:30 amGCM - MDW
1 stop7h 03mMultiple Airlines
Deal found 6/11$634
Sat 7/136:00 amMDW - GCM
1 stop5h 35mDelta
Fri 7/1912:50 pmGCM - MDW
2 stops19h 48mDelta
Deal found 6/12$778
Sun 6/162:26 pmMDW - GCM
1 stop25h 44mMultiple Airlines
Tue 6/1811:30 amGCM - MDW
1 stop7h 11mMultiple Airlines
Deal found 6/12$784
Sat 7/136:00 amMDW - GCM
1 stop5h 35mDelta
Fri 7/1912:50 pmGCM - MDW
1 stop8h 56mDelta
Deal found 6/12$873

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 3,214,720 searches. Data last updated June 13, 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.
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:57 pmGCM - MDW
1 stop8h 41mDelta
Deal found 6/12$453
Fri 9/66:05 pmMDW - GCM
2 stops17h 30mDelta
Fri 9/1312:57 pmGCM - MDW
1 stop8h 41mDelta
Deal found 6/12$458
Sat 12/76:15 pmMDW - GCM
1 stop17h 15mDelta
Thu 12/121:55 pmGCM - MDW
2 stops19h 50mDelta
Deal found 6/12$463
Tue 9/105:45 pmMDW - GCM
2 stops41h 52mDelta
Sun 9/1512:57 pmGCM - MDW
1 stop8h 41mDelta
Deal found 6/12$468
Wed 11/136:50 pmMDW - GCM
1 stop16h 40mDelta
Sun 11/171:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 6/12$488
Sat 11/166:15 pmMDW - GCM
1 stop17h 15mDelta
Sat 11/231:55 pmGCM - MDW
2 stops19h 50mDelta
Deal found 6/12$498
Thu 7/42:36 pmMDW - GCM
1 stop6h 44mMultiple Airlines
Tue 7/911:30 amGCM - MDW
1 stop21h 06mMultiple Airlines
Deal found 6/11$511
Sat 11/166:15 pmMDW - GCM
1 stop17h 15mDelta
Sat 11/231:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 6/12$513
Sat 12/76:00 amMDW - GCM
1 stop5h 30mDelta
Wed 12/111:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 6/12$527

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 3,214,720 searches. Data last updated June 13, 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.
Sat 11/166:15 pmMDW - GCM
1 stop17h 15mDelta
Deal found 6/12$313
Wed 6/196:00 amMDW - GCM
1 stop5h 35mDelta
Deal found 6/13$462
Tue 8/139:44 pmMDW - GCM
3 stops21h 16mMultiple Airlines
Deal found 6/12$479
Tue 8/135:45 pmMDW - GCM
2 stops41h 45mDelta
Deal found 6/12$562
Sat 11/165:00 pmMDW - GCM
2 stops19h 35mWestJet
Deal found 6/12$1,448

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 3,214,720 searches. Data last updated June 13, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$415 - $538

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sat 9/21

1 stop22h 27m

George Town Owen Roberts Intl

Sat 9/28

1 stop10h 08m

$415

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 41m

$453

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

1 stop8h 41m

$458

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sat 12/7

1 stop17h 15m

George Town Owen Roberts Intl

Thu 12/12

2 stops19h 50m

$463

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Tue 9/10

2 stops41h 52m

George Town Owen Roberts Intl

Sun 9/15

1 stop8h 41m

$468

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 9/22

1 stop5h 37m

George Town Owen Roberts Intl

Sat 9/28

1 stop8h 41m

$483

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 7/4

1 stop6h 44m

George Town Owen Roberts Intl

Tue 7/9

1 stop21h 06m

$505

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Thu 7/4

1 stop6h 44m

George Town Owen Roberts Intl

Tue 7/9

1 stop21h 06m

$511

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Wed 7/24

1 stop6h 39m

George Town Owen Roberts Intl

Sun 7/28

1 stop18h 36m

$538

Flights are sorted by cheapest first

Deals found on 6/13

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 13, 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.
8.0
Very good
10,000 reviews

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Overall

8.0

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.

8.0
Very good
10,000 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Overall

8.0

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.

7.5
Good
2,824 reviews
8.0
Very good
10,000 reviews

Comfort

7.9

Boarding

8.2

Crew

8.6

Entertainment

8.0

Overall

8.0

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 $415, but on average you can expect to pay $518.

  • 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 6/12.

  • 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 $447). Flying from Chicago Midway Airport to Cayman Islands in June is currently the most expensive (average of $558). 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

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

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 3,214,720 searches. Data last updated June 13, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$408Average$628FlexibilityNo cancel feeOn-timeN/A

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.
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.