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Cheap flights from Chicago Midway Airport to the Cayman Islands from $187

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to the Cayman Islands departing on 11/15. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:15 am - 12:35 pm
MDW
-
GCM
6h 20m
1 stop
Southwest Logo
1:30 pm - 6:55 pm
GCM
-
MDW
6h 25m
1 stop
$405Southwest
Tue, Nov 3 - Thu, Nov 12
Southwest Logo
5:15 am - 12:35 pm
MDW
-
GCM
6h 20m
1 stop
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
$410Southwest
Tue, Nov 3 - Thu, Nov 12
Southwest Logo
5:15 am - 12:35 pm
MDW
-
GCM
6h 20m
1 stop
Southwest Logo
1:30 pm - 7:35 pm
GCM
-
MDW
7h 05m
1 stop
$425Southwest
Wed, Nov 11 - Wed, Nov 18
Southwest Logo
5:15 am - 12:35 pm
MDW
-
GCM
6h 20m
1 stop
Southwest Logo
1:30 pm - 6:55 pm
GCM
-
MDW
6h 25m
1 stop
$426Southwest
Tue, Nov 3 - Thu, Nov 12
Southwest Logo
8:50 pm - 12:35 pm
MDW
-
GCM
14h 45m
2 stops
Southwest Logo
1:30 pm - 7:35 pm
GCM
-
MDW
7h 05m
1 stop
$430Southwest
Wed, Nov 11 - Wed, Nov 18
Southwest Logo
4:15 pm - 12:35 pm
MDW
-
GCM
19h 20m
2 stops
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
$431Southwest
Tue, Nov 3 - Thu, Nov 12
Southwest Logo
4:15 pm - 12:35 pm
MDW
-
GCM
19h 20m
2 stops
Southwest Logo
1:30 pm - 9:30 pm
GCM
-
MDW
9h 00m
2 stops
$463Southwest
Tue, Dec 1 - Thu, Dec 10
Southwest Logo
5:15 am - 12:35 pm
MDW
-
GCM
6h 20m
1 stop
Southwest Logo
1:30 pm - 9:10 pm
GCM
-
MDW
8h 40m
1 stop
$475Southwest
Tue, Dec 1 - Thu, Dec 10
Southwest Logo
5:15 am - 12:35 pm
MDW
-
GCM
6h 20m
1 stop
Southwest Logo
1:30 pm - 6:55 pm
GCM
-
MDW
6h 25m
1 stop
$513Southwest
Tue, Nov 3 - Fri, Nov 13
Southwest Logo
5:15 am - 12:35 pm
MDW
-
GCM
6h 20m
1 stop
Southwest Logo
1:30 pm - 11:05 pm
GCM
-
MDW
10h 35m
2 stops
$518Southwest
Tue, Nov 3 - Fri, Nov 13

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Southwest flights from Chicago Midway Airport to Cayman Islands

Our best Southwest deals on Chicago Midway Airport to Cayman Islands flight tickets
Southwest
Nov 3
MDW5:15 amChicago Midway
6h 20m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 12
GCM1:30 pmGeorge Town Owen Roberts Intl
6h 25m
1 stop
MDW6:55 pmChicago Midway
$405
Southwest
Nov 3
MDW5:15 amChicago Midway
6h 20m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 12
GCM1:30 pmGeorge Town Owen Roberts Intl
10h 10m
2 stops
MDW10:40 pmChicago Midway
$410
Southwest
Nov 11
MDW5:15 amChicago Midway
6h 20m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 18
GCM1:30 pmGeorge Town Owen Roberts Intl
7h 05m
1 stop
MDW7:35 pmChicago Midway
$425

Delta flights from Chicago Midway Airport to Cayman Islands

Our best Delta deals on Chicago Midway Airport to Cayman Islands flight tickets
Delta
Nov 10
MDW6:00 amChicago Midway
5h 25m
1 stop
GCM12:25 pmGeorge Town Owen Roberts Intl
Nov 11
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
MDW10:10 pmChicago Midway
$611
Delta
Oct 28
MDW6:45 pmChicago Midway
16h 55m
2 stops
GCM11:40 amGeorge Town Owen Roberts Intl
Nov 6
GCM1:55 pmGeorge Town Owen Roberts Intl
20h 23m
2 stops
MDW9:18 amChicago Midway
$616
Delta
Oct 31
MDW6:00 amChicago Midway
5h 40m
1 stop
GCM11:40 amGeorge Town Owen Roberts Intl
Nov 6
GCM1:55 pmGeorge Town Owen Roberts Intl
9h 30m
1 stop
MDW10:25 pmChicago Midway
$646

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport 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, momondo users made 832,500 searches. Data last updated July 4, 2026.
Use the filters below to find and compare flights from Chicago Midway Airport to the Cayman Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 11/3

5:15 am-12:35 pm

1 stop6h 20m

George Town Owen Roberts Intl

Thu 11/12

1:30 pm-6:55 pm

1 stop6h 25m

$405

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 11/3

5:15 am-12:35 pm

1 stop6h 20m

George Town Owen Roberts Intl

Thu 11/12

1:30 pm-10:40 pm

2 stops10h 10m

$410

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 11/11

5:15 am-12:35 pm

1 stop6h 20m

George Town Owen Roberts Intl

Wed 11/18

1:30 pm-7:35 pm

1 stop7h 05m

$425

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 11/3

5:15 am-12:35 pm

1 stop6h 20m

George Town Owen Roberts Intl

Thu 11/12

1:30 pm-6:55 pm

1 stop6h 25m

$426

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 11/11

8:50 pm-12:35 pm

2 stops14h 45m

George Town Owen Roberts Intl

Wed 11/18

1:30 pm-7:35 pm

1 stop7h 05m

$430

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 11/3

4:15 pm-12:35 pm

2 stops19h 20m

George Town Owen Roberts Intl

Thu 11/12

1:30 pm-10:40 pm

2 stops10h 10m

$431

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 12/1

4:15 pm-12:35 pm

2 stops19h 20m

George Town Owen Roberts Intl

Thu 12/10

1:30 pm-9:30 pm

2 stops9h 00m

$463

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 12/1

5:15 am-12:35 pm

1 stop6h 20m

George Town Owen Roberts Intl

Thu 12/10

1:30 pm-9:10 pm

1 stop8h 40m

$475

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 11/3

5:15 am-12:35 pm

1 stop6h 20m

George Town Owen Roberts Intl

Fri 11/13

1:30 pm-6:55 pm

1 stop6h 25m

$513

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 11/3

5:15 am-12:35 pm

1 stop6h 20m

George Town Owen Roberts Intl

Fri 11/13

1:30 pm-11:05 pm

2 stops10h 35m

$518

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Chicago Midway Airport to Cayman Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago Midway to Cayman Islands?

Southwest is the most popular carrier operating from Chicago Midway to Cayman Islands

Cheap Chicago Midway Airport to Cayman Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago Midway Airport to Cayman Islands

Fastest flight time

5h 28m

Direct flights

None
The fastest flight from Chicago Midway Airport to Cayman Islands takes 5h 28m
There are no direct flights from Chicago Midway Airport to Cayman Islands. There are no popular flight routes from Chicago Midway Airport to Cayman Islands.
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Frequently asked questions about flying from Chicago Midway Airport to the Cayman Islands

  • When did momondo last update prices for flights from Chicago Midway Airport to Cayman Islands?

    Prices for flights from Chicago Midway Airport to Cayman Islands are updated daily.

  • How old do you have to be to fly from Chicago Midway Airport to Cayman Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago Midway Airport to Cayman Islands.

  • What documentation or ID do you need to fly to Cayman Islands?

    The travel and health documents required for your trip to Cayman Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Cayman Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cayman Islands?

Finding the right flight to Cayman Islands from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Cayman Islands quick and easy, saving you time and money.

Can I find flights from Chicago to Cayman Islands with flexible booking policies on momondo?

All flight searches from Chicago to Cayman Islands on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Chicago to Cayman Islands?

Once you have performed a search for Chicago to Cayman Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Cayman Islands right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Cayman Islands from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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