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.

$270 Cheap Flights from Cayman Islands to Chicago Midway Airport in 2026

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0 bags

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Find the cheapest flights from the Cayman Islands to Chicago

Round-trip

One-way

Last minute

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

Enter your travel dates to find the best prices.

1:05 pm - 12:05 am

GCM

MDW

11h 00m

1 stop

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$422Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 11:30 pm

GCM

MDW

10h 25m

2 stops

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$427Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 10:45 pm

GCM

MDW

9h 40m

2 stops

6:25 pm - 12:10 pm

MDW

GCM

17h 45m

2 stops

$478Southwest

Thu, Apr 23 - Mon, Apr 27

1:05 pm - 12:05 am

GCM

MDW

11h 00m

1 stop

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$510Southwest

Mon, Apr 13 - Mon, Apr 20

1:05 pm - 10:45 pm

GCM

MDW

9h 40m

2 stops

5:35 am - 12:10 pm

MDW

GCM

6h 35m

1 stop

$515Southwest

Mon, Apr 13 - Mon, Apr 20

1:05 pm - 10:45 pm

GCM

MDW

9h 40m

2 stops

5:30 am - 12:10 pm

MDW

GCM

6h 40m

2 stops

$527Southwest

Mon, Apr 13 - Mon, Apr 20

11:50 am - 7:05 pm

GCM

MDW

7h 15m

1 stop

9:40 pm - 12:10 pm

MDW

GCM

14h 30m

2 stops

$558Southwest

Mon, Mar 30 - Mon, Apr 6

1:15 pm - 10:19 pm

GCM

MDW

33h 04m

2 stops

12:55 pm - 12:44 pm

MDW

GCM

23h 49m

1 stop

$570Multiple Airlines

Sat, Mar 28 - Sat, Apr 4

11:50 am - 12:05 am

GCM

MDW

12h 15m

2 stops

6:25 pm - 12:10 pm

MDW

GCM

17h 45m

2 stops

$598Southwest

Mon, Mar 30 - Mon, Apr 6

12:40 pm - 11:35 pm

GCM

MDW

10h 55m

2 stops

6:20 pm - 12:00 pm

MDW

GCM

17h 40m

2 stops

$652Southwest

Fri, Mar 27 - Sat, Apr 4

Delta flights from Cayman Islands to Chicago Midway Airport

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

Delta

Apr 14

GCM1:25 pmGeorge Town Owen Roberts Intl

19h 22m

2 stops

MDW8:47 amChicago Midway

Apr 21

MDW6:00 amChicago Midway

6h 00m

1 stop

GCM12:00 pmGeorge Town Owen Roberts Intl

$510

Delta

Apr 14

GCM1:25 pmGeorge Town Owen Roberts Intl

19h 22m

2 stops

MDW8:47 amChicago Midway

Apr 23

MDW1:24 pmChicago Midway

22h 36m

2 stops

GCM12:00 pmGeorge Town Owen Roberts Intl

$540

Delta

Mar 30

GCM1:12 pmGeorge Town Owen Roberts Intl

9h 19m

1 stop

MDW10:31 pmChicago Midway

Apr 6

MDW6:00 amChicago Midway

5h 47m

1 stop

GCM11:47 amGeorge Town Owen Roberts Intl

$1,146

Southwest flights from Cayman Islands to Chicago Midway Airport

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

Southwest

Apr 23

GCM1:05 pmGeorge Town Owen Roberts Intl

11h 00m

1 stop

MDW12:05 amChicago Midway

Apr 27

MDW5:35 amChicago Midway

6h 35m

1 stop

GCM12:10 pmGeorge Town Owen Roberts Intl

$422

Southwest

Apr 23

GCM1:05 pmGeorge Town Owen Roberts Intl

10h 25m

2 stops

MDW11:30 pmChicago Midway

Apr 27

MDW5:35 amChicago Midway

6h 35m

1 stop

GCM12:10 pmGeorge Town Owen Roberts Intl

$427

Southwest

May 4

GCM1:05 pmGeorge Town Owen Roberts Intl

11h 00m

1 stop

MDW12:05 amChicago Midway

May 5

MDW6:00 amChicago Midway

6h 10m

1 stop

GCM12:10 pmGeorge Town Owen Roberts Intl

$459

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

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$422

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-11:30 pm

2 stops10h 25m

Chicago Midway

Mon 4/27

5:35 am-12:10 pm

1 stop6h 35m

$427

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 4/23

1:05 pm-10:45 pm

2 stops9h 40m

Chicago Midway

Mon 4/27

6:25 pm-12:10 pm

2 stops17h 45m

$478

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 4/13

1:05 pm-12:05 am

1 stop11h 00m

Chicago Midway

Mon 4/20

5:35 am-12:10 pm

1 stop6h 35m

$510

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 4/13

1:05 pm-10:45 pm

2 stops9h 40m

Chicago Midway

Mon 4/20

5:35 am-12:10 pm

1 stop6h 35m

$515

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 4/13

1:05 pm-10:45 pm

2 stops9h 40m

Chicago Midway

Mon 4/20

5:30 am-12:10 pm

2 stops6h 40m

$527

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 3/30

11:50 am-7:05 pm

1 stop7h 15m

Chicago Midway

Mon 4/6

9:40 pm-12:10 pm

2 stops14h 30m

$558

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 3/28

1:15 pm-10:19 pm

2 stops33h 04m

Chicago Midway

Sat 4/4

12:55 pm-12:44 pm

1 stop23h 49m

$570

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 3/30

11:50 am-12:05 am

2 stops12h 15m

Chicago Midway

Mon 4/6

6:25 pm-12:10 pm

2 stops17h 45m

$598

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 3/27

12:40 pm-11:35 pm

2 stops10h 55m

Chicago Midway

Sat 4/4

6:20 pm-12:00 pm

2 stops17h 40m

$652

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 is the most popular carrier 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

Fastest flight time	9h 00m
Direct flights	None

The fastest flight from Cayman Islands to Chicago Midway Airport takes 9h 00m

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

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

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Munster

Crown Point

Chesterton

Monticello

Porter

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.