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Cayman Islands

$186+ 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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
Nov 25 — Dec 21
Mon 11/25
Mon 12/2
1 adult, Economy
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Cheap flight deals from Midway to Cayman Islands

Discover tips and strategies to find the most affordable flight options for your journey from Midway (MDW) to Cayman Islands (KY0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated November 20, 2024.

Find flight deals from Midway to Cayman Islands

Cheapest flights from Midway to Cayman Islands
Explore the most affordable flight options available from Midway to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2024.

This Southwest deal was found by Cheapflights users on 11/19. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/96:00 amMDW - GCM
1 stop5h 55mSouthwest
Thu 12/121:50 pmGCM - MDW
2 stops9h 30mSouthwest
Deal found 11/19$575
This Delta deal was found by Cheapflights users on 11/19. 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 12/306:00 amMDW - GCM
1 stop5h 27mDelta
Wed 1/82:09 pmGCM - MDW
1 stop9h 11mDelta
Deal found 11/19$618
This Kiwi.com deal was found by Cheapflights users on 11/19. 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 12/65:01 amMDW - GCM
1 stop9h 44mMultiple Airlines
Wed 12/1111:30 amGCM - MDW
1 stop28h 42mMultiple Airlines
Deal found 11/19$661
This Mytrip deal was found by Cheapflights users on 11/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/49:30 amMDW - GCM
3 stops27h 19mWestJet
Sun 12/82:50 pmGCM - MDW
2 stops28h 42mWestJet
Deal found 11/19$795

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 2,629,791 searches. Data last updated November 20, 2024.

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Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 2/19

7:25 am-4:10 pm

1 stop7h 45m

George Town Owen Roberts Intl

Fri 2/28

4:45 pm-8:44 am

1 stop16h 59m

$488

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 1/1

6:00 am-12:55 pm

1 stop5h 55m

George Town Owen Roberts Intl

Wed 1/8

1:50 pm-9:20 am

2 stops20h 30m

$572

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 1/12

6:00 am-12:44 pm

1 stop5h 44m

George Town Owen Roberts Intl

Tue 1/14

2:09 pm-10:20 pm

1 stop9h 11m

$588

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/4

9:30 am-1:49 pm

3 stops27h 19m

George Town Owen Roberts Intl

Sun 12/8

2:50 pm-6:32 pm

2 stops28h 42m

$795

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/27

6:15 am-4:10 pm

2 stops8h 55m

$186

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 3/1

4:45 pm-12:55 pm

2 stops19h 10m

$225

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 12/23

6:00 am-2:32 pm

1 stop7h 32m

$297

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 1/18

11:19 am-1:49 pm

2 stops25h 30m

$353

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/19

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.

Travel insights for flights from Midway to Cayman Islands

Get recent, data-driven insights about flights from Midway to Cayman Islands including ideal travel times, pricing trends, and more.
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 November 20, 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.
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,014 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,756 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,014 reviews

Comfort

8.1

Crew

8.7

Boarding

8.2

Overall

8.1

Food

7.2

Entertainment

7.7

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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.

  • What are the cheapest airlines to fly from Chicago Midway Airport to Cayman Islands one-way?

    For one-way options, check prices for Southwest. According to our data, you can fly for as low as $225. Users have also found prices from $297 and $353 on Delta and WestJet, respectively.

  • 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.

  • 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 $467). 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.

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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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