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Cayman Islands

$161+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
MDW — GCM
janv. 28 — févr. 41
mar. 1/28
mar. 2/4
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 janvier 23, 2025.

Round-trip from

$590
(Southwest)

One-way from

$161
(Trip.com)
From Chicago Midway to Cayman Islands
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One-way flight from Chicago Midway to Cayman Islands
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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 janvier 23, 2025.

This Southwest deal was found by Cheapflights users on 1/22. 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.
mer. 3/125:00 pmMDW - GCM
2 stops18h 45mSouthwest
mer. 3/1912:40 pmGCM - MDW
1 stop10h 20mSouthwest
Deal found 1/22$590
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
sam. 2/154:19 pmMDW - GCM
1 stop22h 51mMultiple Airlines
mer. 2/1911:30 amGCM - MDW
1 stop28h 43mMultiple Airlines
Deal found 1/21$595
This Delta deal was found by Cheapflights users on 1/22. 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.
mer. 3/56:00 amMDW - GCM
1 stop5h 38mDelta
mer. 3/191:03 pmGCM - MDW
1 stop9h 20mDelta
Deal found 1/22$610
This Mytrip deal was found by Cheapflights users on 1/22. 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.
dim. 3/2310:25 amMDW - GCM
3 stops26h 18mWestJet
lun. 3/311:50 pmGCM - MDW
2 stops28h 28mWestJet
Deal found 1/22$826

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 2,558,603 searches. Data last updated janvier 23, 2025.

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mer. 3/12

5:00 pm-11:45 am

2 stops18h 45m

George Town Owen Roberts Intl

mer. 3/19

12:40 pm-11:00 pm

1 stop10h 20m

$590

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sam. 2/15

4:19 pm-4:10 pm

1 stop22h 51m

George Town Owen Roberts Intl

mer. 2/19

11:30 am-3:13 pm

1 stop28h 43m

$595

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mer. 3/5

6:00 am-12:38 pm

1 stop5h 38m

George Town Owen Roberts Intl

mer. 3/19

1:03 pm-10:23 pm

1 stop9h 20m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dim. 3/23

10:25 am-12:43 pm

3 stops26h 18m

George Town Owen Roberts Intl

lun. 3/31

1:50 pm-6:18 pm

2 stops28h 28m

$826

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mar. 4/8

6:00 am-4:10 pm

1 stop10h 10m

$161

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sam. 3/29

8:55 pm-11:50 am

2 stops14h 55m

$218

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mer. 4/9

6:00 am-11:25 am

1 stop5h 25m

$288

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sam. 2/8

10:57 am-1:43 pm

2 stops25h 46m

$1,260

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/23

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 janvier 23, 2025.
Read reviews from past customers who have flown Southwest and Delta 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
4,652 reviews

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,652 reviews
Southwest
8.1
Very good
4,652 reviews

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,512 reviews
Southwest
8.1
Very good
4,652 reviews

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,828 reviews
Southwest
8.1
Very good
4,652 reviews

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $218. Users have also found prices from $288 and $1,260 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 March is currently the most expensive (average of $594). 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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See prices for flight routes from nearby airports that may be better suited for you.
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