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.

$218 Cheap Flights from Chicago Midway Airport to Cayman Islands in 2026

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

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

7:55 pm - 12:55 pm

MDW

GCM

16h 00m

2 stops

12:40 pm - 9:55 pm

GCM

MDW

9h 15m

2 stops

$364Southwest

Tue, Mar 3 - Tue, Mar 10

6:15 am - 9:15 pm

MDW

GCM

14h 00m

1 stop

2:49 pm - 7:47 pm

GCM

MDW

29h 58m

2 stops

$400Multiple Airlines

Thu, Feb 19 - Sun, Feb 22

6:00 am - 4:05 pm

MDW

GCM

10h 05m

2 stops

7:00 am - 1:41 pm

GCM

MDW

6h 41m

1 stop

$406Multiple Airlines

Tue, Mar 17 - Mon, Mar 23

6:15 am - 9:15 pm

MDW

GCM

14h 00m

1 stop

7:00 am - 1:41 pm

GCM

MDW

7h 41m

1 stop

$409Multiple Airlines

Thu, Feb 26 - Fri, Mar 6

5:00 am - 12:55 pm

MDW

GCM

6h 55m

1 stop

12:40 pm - 7:20 pm

GCM

MDW

6h 40m

1 stop

$410Southwest

Tue, Mar 3 - Tue, Mar 10

9:50 pm - 12:10 pm

MDW

GCM

14h 20m

2 stops

1:05 pm - 10:45 pm

GCM

MDW

9h 40m

2 stops

$415Southwest

Sun, Apr 19 - Thu, Apr 23

6:00 am - 11:35 am

MDW

GCM

28h 35m

1 stop

1:15 pm - 10:19 pm

GCM

MDW

33h 04m

2 stops

$437Multiple Airlines

Sat, Mar 7 - Sat, Mar 14

8:45 pm - 12:55 pm

MDW

GCM

15h 10m

2 stops

1:50 pm - 7:50 am

GCM

MDW

19h 00m

2 stops

$449Southwest

Sat, Feb 28 - Wed, Mar 4

6:25 pm - 12:57 pm

MDW

GCM

18h 32m

2 stops

4:25 pm - 10:05 am

GCM

MDW

17h 40m

1 stop

$452Multiple Airlines

Sat, Apr 11 - Sat, Apr 18

6:30 am - 9:35 pm

MDW

GCM

15h 05m

1 stop

4:25 pm - 10:05 am

GCM

MDW

17h 40m

1 stop

$464Multiple Airlines

Fri, Apr 3 - Thu, Apr 9

Delta flights from Chicago Midway Airport to Cayman Islands

Our best Delta deals on Chicago Midway Airport to Cayman Islands flight tickets

Delta

Feb 19

MDW6:00 amChicago Midway

5h 29m

1 stop

GCM12:29 pmGeorge Town Owen Roberts Intl

Feb 24

GCM1:54 pmGeorge Town Owen Roberts Intl

9h 39m

1 stop

MDW10:33 pmChicago Midway

$499

Delta

Mar 2

MDW6:00 amChicago Midway

5h 29m

1 stop

GCM12:29 pmGeorge Town Owen Roberts Intl

Mar 6

GCM1:54 pmGeorge Town Owen Roberts Intl

9h 37m

1 stop

MDW10:31 pmChicago Midway

$505

Delta

Mar 22

MDW6:00 amChicago Midway

5h 47m

1 stop

GCM11:47 amGeorge Town Owen Roberts Intl

Mar 25

GCM1:12 pmGeorge Town Owen Roberts Intl

23h 17m

2 stops

MDW12:29 pmChicago Midway

$510

Southwest flights from Chicago Midway Airport to Cayman Islands

Our best Southwest deals on Chicago Midway Airport to Cayman Islands flight tickets

Southwest

Mar 3

MDW7:55 pmChicago Midway

16h 00m

2 stops

GCM12:55 pmGeorge Town Owen Roberts Intl

Mar 10

GCM12:40 pmGeorge Town Owen Roberts Intl

9h 15m

2 stops

MDW9:55 pmChicago Midway

$364

Southwest

Mar 3

MDW5:00 amChicago Midway

6h 55m

1 stop

GCM12:55 pmGeorge Town Owen Roberts Intl

Mar 10

GCM12:40 pmGeorge Town Owen Roberts Intl

6h 40m

1 stop

MDW7:20 pmChicago Midway

$410

Southwest

Apr 19

MDW9:50 pmChicago Midway

14h 20m

2 stops

GCM12:10 pmGeorge Town Owen Roberts Intl

Apr 23

GCM1:05 pmGeorge Town Owen Roberts Intl

9h 40m

2 stops

MDW10:45 pmChicago Midway

$415

momondo Fare Finder

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

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/3

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

Tue 3/10

12:40 pm-9:55 pm

2 stops9h 15m

$364

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 2/19

6:15 am-9:15 pm

1 stop14h 00m

George Town Owen Roberts Intl

Sun 2/22

2:49 pm-7:47 pm

2 stops29h 58m

$400

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/17

6:00 am-4:05 pm

2 stops10h 05m

George Town Owen Roberts Intl

Mon 3/23

7:00 am-1:41 pm

1 stop6h 41m

$406

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 2/26

6:15 am-9:15 pm

1 stop14h 00m

George Town Owen Roberts Intl

Fri 3/6

7:00 am-1:41 pm

1 stop7h 41m

$409

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/3

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Tue 3/10

12:40 pm-7:20 pm

1 stop6h 40m

$410

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/19

9:50 pm-12:10 pm

2 stops14h 20m

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-10:45 pm

2 stops9h 40m

$415

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 3/7

6:00 am-11:35 am

1 stop28h 35m

George Town Owen Roberts Intl

Sat 3/14

1:15 pm-10:19 pm

2 stops33h 04m

$437

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 2/28

8:45 pm-12:55 pm

2 stops15h 10m

George Town Owen Roberts Intl

Wed 3/4

1:50 pm-7:50 am

2 stops19h 00m

$449

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 4/11

6:25 pm-12:57 pm

2 stops18h 32m

George Town Owen Roberts Intl

Sat 4/18

4:25 pm-10:05 am

1 stop17h 40m

$452

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 4/3

6:30 am-9:35 pm

1 stop15h 05m

George Town Owen Roberts Intl

Thu 4/9

4:25 pm-10:05 am

1 stop17h 40m

$464

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first

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 and Delta are the most popular carriers 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 24m
Direct flights	None

The fastest flight from Chicago Midway Airport to Cayman Islands takes 5h 24m

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.

Search flight deals

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.

An easier way to manage your Cayman Islands trip

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Popular cities in the Cayman Islands

Flights to George Townfrom $199

Flights to Cayman Bracfrom $319

Flights to Little Caymanfrom $328

Cheap flights from Chicago Midway Airport to the Cayman Islands from $218

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Big names and deals

Filter for what you want

Filter for what you want

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

Cheap round-trip flights

Cheap one-way flights

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Delta flights from Chicago Midway Airport to Cayman Islands

Our best Delta deals on Chicago Midway Airport to Cayman Islands flight tickets

Southwest flights from Chicago Midway Airport to Cayman Islands

Our best Southwest deals on Chicago Midway Airport to Cayman Islands flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Chicago Midway Airport to the Cayman Islands that are best for you.

See travel insights to the Cayman Islands from

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

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

Southwest and Delta are the most popular carriers 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

Direct flights

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

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

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

Why use momondo?

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

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

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

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

An easier way to manage your Cayman Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the Cayman Islands

Popular cities in the Cayman Islands

Popular flights according to clicks in the last 7 days on momondo

Chicago Midway Airport flight routes

According to popular flight searches on momondo this year

Cayman Islands flight routes

According to popular flight searches on momondo this year

Fly your favorite airline to the Cayman Islands

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to the Cayman Islands

List of cabin classes available on flights landing in the Cayman Islands. Availability may vary depending on flight origin and airline.

Complete your trip to the Cayman Islands

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