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

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 Cayman Islands to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

$297 Cheap Flights from Cayman Islands to Chicago Midway Airport in 2026

Find the cheapest flights from the Cayman Islands to Chicago

Round-trip

One-way

Recent round-trip flight deals from the Cayman Islands to Chicago

Enter your travel dates to find the best prices.

1:50 pm - 10:50 pmGCM George Town Owen Roberts Intl-MDW Chicago Midway

10h 00m1 stop Orlando

7:55 pm - 12:55 pmMDW Chicago Midway-GCM George Town Owen Roberts Intl

16h 00m2 stops Phoenix Sky Harbor Intl Orlando

$509Southwest

Fri, Jan 22 - Mon, Jan 25

1:50 pm - 10:50 pmGCM George Town Owen Roberts Intl-MDW Chicago Midway

10h 00m1 stop Orlando

5:45 am - 12:55 pmMDW Chicago Midway-GCM George Town Owen Roberts Intl

6h 10m1 stop Orlando

$529Southwest

Fri, Jan 22 - Mon, Jan 25

7:00 am - 11:44 pmGCM George Town Owen Roberts Intl-MDW Chicago Midway

16h 44m2 stops Miami Atlanta Hartsfield-Jackson

6:25 am - 9:15 pmMDW Chicago Midway-GCM George Town Owen Roberts Intl

14h 50m2 stops Atlanta Hartsfield-Jackson Miami

$530Multiple Airlines

Thu, Oct 1 - Mon, Oct 5

1:00 pm - 10:44 pmGCM George Town Owen Roberts Intl-MDW Chicago Midway

9h 44m1 stop Atlanta Hartsfield-Jackson

6:04 am - 11:40 amMDW Chicago Midway-GCM George Town Owen Roberts Intl

5h 36m1 stop Atlanta Hartsfield-Jackson

$817Delta

Mon, Oct 5 - Mon, Oct 12

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Southwest flights from Cayman Islands to Chicago Midway Airport

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

Southwest

Jan 22

GCM1:50 pmGeorge Town Owen Roberts Intl

10h 00m

1 stop

MDW10:50 pmChicago Midway

Jan 25

MDW7:55 pmChicago Midway

16h 00m

2 stops

GCM12:55 pmGeorge Town Owen Roberts Intl

$509

Southwest

Jan 22

GCM1:50 pmGeorge Town Owen Roberts Intl

10h 00m

1 stop

MDW10:50 pmChicago Midway

Jan 25

MDW5:45 amChicago Midway

6h 10m

1 stop

GCM12:55 pmGeorge Town Owen Roberts Intl

$529

momondo Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Fri 1/22

1:50 pm-10:50 pm

1 stop10h 00m

Chicago Midway

Mon 1/25

7:55 pm-12:55 pm

2 stops16h 00m

$509

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Fri 1/22

1:50 pm-10:50 pm

1 stop10h 00m

Chicago Midway

Mon 1/25

5:45 am-12:55 pm

1 stop6h 10m

$529

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Thu 10/1

7:00 am-11:44 pm

2 stops16h 44m

Chicago Midway

Mon 10/5

6:25 am-9:15 pm

2 stops14h 50m

$530

Quickest round-trip

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Mon 10/5

1:00 pm-10:44 pm

1 stop9h 44m

Chicago Midway

Mon 10/12

6:04 am-11:40 am

1 stop5h 36m

$817

Cheapest one-way

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Wed 11/11

1:30 pm-10:40 pm

2 stops10h 10m

$297

Quickest one-way

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Wed 11/11

1:30 pm-9:15 pm

1 stop8h 45m

$302

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Fri 10/2

11:25 am-5:51 pm

2 stops30h 26m

$355

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Sat 11/14

8:50 am-10:58 am

2 stops51h 08m

$383

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Thu 9/3

7:00 am-10:47 pm

2 stops15h 47m

$428

George TownChicago

GCM George Town Owen Roberts Intl - MDW Chicago Midway

GCMMDW

George Town Owen Roberts Intl

Fri 10/2

1:00 pm-10:44 pm

1 stop9h 44m

$429

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 Cayman Islands to Chicago Midway Airport

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 Cayman Islands to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Cayman Islands to Chicago Midway

Cheap Cayman Islands to Chicago Midway Airport flight deals and tips

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

Best Price Found	$297
Fastest flight time	10h 10m
Direct flights	None

The best one-way flight to Chicago Midway Airport from Cayman Islands in the past 72 hours is $297. The best round-trip flight deal from Cayman Islands to Chicago Midway Airport found on momondo in the last 72 hours is $509.

The fastest flight from Cayman Islands to Chicago Midway Airport takes 10h 10m

There are no direct flights from Cayman Islands to Chicago Midway Airport. There are no popular flight routes from Cayman Islands to Chicago Midway Airport.

Search flight deals

Frequently asked questions about flying from the Cayman Islands to Chicago Midway Airport

When did momondo last update prices for flights from Cayman Islands to Chicago Midway Airport?
Prices for flights from Cayman Islands to Chicago Midway Airport are updated daily.
How old do you have to be to fly from Cayman Islands to Chicago Midway Airport?
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 Cayman Islands to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

Merrillville

New Buffalo

Hammond

Portage

Benton Harbor

Lansing

Saint Joseph

Valparaiso

Schererville

Munster

Chesterton

Monticello

Porter

Crown Point

Griffith

Saint John

Why use momondo?

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

Finding the right flight to Chicago from Cayman Islands 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 Chicago quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Chicago from Cayman Islands with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Cayman Islands.

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

Price alerts on flights to Chicago from Cayman Islands are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.