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$215+ Cheap flights from Midway (MDW) to the Cayman Islands

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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Jul 30 — Aug 61
From?
To?
Tue 7/30
Tue 8/6
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 82% 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 March. Prices are generally better when you fly from Chicago Midway Airport to Cayman Islands in October, with the cheapest ticket starting at $384.

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 July & August 2024

Find cheap flight options from Midway to Cayman Islands specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on July 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in July and August 2024. Check back soon for alternative fares.
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/226:55 pmMDW - GCM
1 stop16h 35mDelta
Thu 8/2912:50 pmGCM - MDW
1 stop8h 56mDelta
Deal found 7/25$538
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/226:55 pmMDW - GCM
1 stop16h 35mDelta
Thu 8/2912:50 pmGCM - MDW
2 stops19h 48mDelta
Deal found 7/25$543
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/99:31 amMDW - GCM
1 stop11h 49mMultiple Airlines
Mon 8/122:00 pmGCM - MDW
1 stop6h 04mMultiple Airlines
Deal found 7/25$601
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/99:31 amMDW - GCM
1 stop11h 49mMultiple Airlines
Sat 8/1711:30 amGCM - MDW
1 stop8h 32mMultiple Airlines
Deal found 7/25$620
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/99:31 amMDW - GCM
1 stop11h 49mMultiple Airlines
Sat 8/179:10 amGCM - MDW
2 stops14h 47mMultiple Airlines
Deal found 7/25$633
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/59:31 amMDW - GCM
1 stop6h 39mMultiple Airlines
Fri 8/94:45 pmGCM - MDW
1 stop15h 51mMultiple Airlines
Deal found 7/24$634
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/99:31 amMDW - GCM
1 stop11h 49mMultiple Airlines
Mon 8/129:30 amGCM - MDW
2 stops14h 05mMultiple Airlines
Deal found 7/25$682
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/59:31 amMDW - GCM
1 stop6h 39mMultiple Airlines
Fri 8/97:00 amGCM - MDW
2 stops16h 35mMultiple Airlines
Deal found 7/24$705
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/126:11 amMDW - GCM
1 stop5h 19mDelta
Mon 8/1912:50 pmGCM - MDW
1 stop8h 56mDelta
Deal found 7/24$728

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 2,752,877 searches. Data last updated July 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in July and August 2024. Check back soon for alternative fares.
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/106:00 amMDW - GCM
1 stop5h 30mDelta
Tue 11/191:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 7/23$438
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/111:10 pmMDW - GCM
2 stops22h 20mDelta
Fri 11/151:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 7/23$443
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/276:00 amMDW - GCM
1 stop5h 33mDelta
Fri 11/112:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 7/23$463
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/116:00 amMDW - GCM
1 stop5h 30mDelta
Mon 11/181:55 pmGCM - MDW
2 stops19h 50mDelta
Deal found 7/23$468
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/28:13 pmMDW - GCM
1 stop22h 27mMultiple Airlines
Sat 11/99:10 amGCM - MDW
1 stop11h 08mMultiple Airlines
Deal found 7/23$471
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/276:00 amMDW - GCM
1 stop5h 33mDelta
Sun 11/31:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 7/23$488
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/268:13 pmMDW - GCM
1 stop22h 27mMultiple Airlines
Fri 11/111:05 amGCM - MDW
1 stop7h 43mMultiple Airlines
Deal found 7/23$499
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/166:15 pmMDW - GCM
1 stop17h 15mDelta
Sat 11/231:55 pmGCM - MDW
1 stop20h 22mDelta
Deal found 7/25$503
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/66:11 amMDW - GCM
1 stop5h 19mDelta
Fri 9/1312:53 pmGCM - MDW
1 stop8h 45mDelta
Deal found 7/24$513

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 2,752,877 searches. Data last updated July 25, 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.
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/29:31 amMDW - GCM
1 stop11h 49mMultiple Airlines
Mon 8/52:00 pmGCM - MDW
1 stop6h 04mMultiple Airlines
Deal found 7/24$772
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - GCM
1 stop20h 33mMultiple Airlines
Mon 8/59:30 amGCM - MDW
2 stops14h 05mMultiple Airlines
Deal found 7/24$784
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - GCM
1 stop20h 33mMultiple Airlines
Mon 8/59:30 amGCM - MDW
2 stops14h 05mMultiple Airlines
Deal found 7/24$787
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/42:30 pmMDW - GCM
1 stop25h 40mMultiple Airlines
Sun 8/112:00 pmGCM - MDW
1 stop7h 36mMultiple Airlines
Deal found 7/23$789
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - GCM
1 stop20h 33mMultiple Airlines
Mon 8/52:00 pmGCM - MDW
1 stop6h 04mMultiple Airlines
Deal found 7/24$799
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/307:37 pmMDW - GCM
1 stop20h 33mMultiple Airlines
Mon 8/52:00 pmGCM - MDW
1 stop6h 04mMultiple Airlines
Deal found 7/24$833
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/25:15 pmMDW - GCM
1 stop19h 24mMultiple Airlines
Mon 8/59:30 amGCM - MDW
2 stops14h 05mMultiple Airlines
Deal found 7/24$880
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/46:00 amMDW - GCM
1 stop5h 30mDelta
Sun 8/1112:50 pmGCM - MDW
2 stops19h 48mDelta
Deal found 7/23$1,311

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 2,752,877 searches. Data last updated July 25, 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.
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/311:38 pmMDW - GCM
1 stop26h 32mMultiple Airlines
Deal found 7/25$215
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/86:55 pmMDW - GCM
1 stop16h 36mDelta
Deal found 7/24$257
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/313:00 pmMDW - GCM
2 stops27h 40mMultiple Airlines
Deal found 7/25$282
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/166:15 pmMDW - GCM
1 stop17h 15mDelta
Deal found 7/25$293
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/276:05 pmMDW - GCM
2 stops41h 25mDelta
Deal found 7/25$327
This CheapOair deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/162:05 pmMDW - GCM
2 stops22h 44mWestJet
Deal found 7/25$1,237

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 2,752,877 searches. Data last updated July 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$438 - $1,178

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 11/10

1 stop5h 30m

George Town Owen Roberts Intl

Fri 11/15

1 stop8h 49m

$438

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 11/11

2 stops17h 31m

George Town Owen Roberts Intl

Tue 11/19

1 stop8h 49m

$443

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 10/27

1 stop5h 33m

George Town Owen Roberts Intl

Fri 11/1

1 stop8h 54m

$463

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 11/11

1 stop5h 30m

George Town Owen Roberts Intl

Mon 11/18

2 stops19h 50m

$468

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sat 11/2

1 stop22h 27m

George Town Owen Roberts Intl

Sat 11/9

1 stop11h 08m

$471

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 10/27

1 stop5h 33m

George Town Owen Roberts Intl

Sun 11/3

1 stop8h 49m

$488

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sat 10/26

1 stop22h 27m

George Town Owen Roberts Intl

Fri 11/1

1 stop7h 43m

$499

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Wed 10/23

1 stop25h 07m

George Town Owen Roberts Intl

Sun 10/27

1 stop9h 29m

$527

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Fri 8/9

2 stops22h 15m

George Town Owen Roberts Intl

Sat 8/17

2 stops23h 58m

$1,178

Flights are sorted by cheapest first

Deals found on 7/23

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 July 25, 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
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Delta
8.0
Very good
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

WestJet
7.4
Good
2,761 reviews
Delta
8.0
Very good
9,630 reviews

Entertainment

8.0

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.4

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

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 $438, but on average you can expect to pay $515.

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

    There are currently 8+ 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 7/25.

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

    Currently, January is the cheapest month in which you can book a flight from Chicago Midway Airport to Cayman Islands (average of $454). 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

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See prices for flight routes from nearby airports that may be better suited for you.

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Midway to Nassau flights
O'Hare Intl to St. John's flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Kingston flights
O'Hare Intl to Christiansted flights
Midway to Santo Domingo flights
Midway to George Town flights
Midway to Simpson Bay flights
O'Hare Intl to Puerto Plata flights
Midway to Providenciales flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Gregory Town flights
Midway to Castries flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to St. George's flights
O'Hare Intl to Havana flights
O'Hare Intl to Kingstown flights
O'Hare Intl to Freeport flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Fort-de-France flights
Midway to Kingston flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Castries flights
O'Hare Intl to Aguadilla flights
O'Hare Intl to Road Town flights
Midway to Santiago de los Caballeros flights
Midway to St. John's flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Ponce flights
Midway to Georgetown flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to The Valley flights

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 2,752,877 searches. Data last updated July 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$409Average$598FlexibilityNo cancel feeOn-timeN/A
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