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.

$254 Cheap Flights from Cayman Islands to Chicago Midway Airport in 2026

1 adult

0 bags

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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.

1:54 pm - 10:31 pm

GCM

MDW

9h 37m

1 stop

6:00 am - 12:29 pm

MDW

GCM

5h 29m

1 stop

$474Delta

Sat, Feb 21 - Wed, Feb 25

1:54 pm - 10:31 pm

GCM

MDW

9h 37m

1 stop

6:00 am - 12:29 pm

MDW

GCM

5h 29m

1 stop

$523Delta

Wed, Feb 25 - Wed, Mar 4

12:45 pm - 9:20 pm

GCM

MDW

8h 35m

1 stop

8:40 pm - 11:50 am

MDW

GCM

15h 10m

2 stops

$602Southwest

Thu, Jun 11 - Sun, Jun 14

12:45 pm - 9:20 pm

GCM

MDW

8h 35m

1 stop

5:20 am - 11:50 am

MDW

GCM

6h 30m

1 stop

$647Southwest

Thu, Jun 11 - Sun, Jun 14

1:25 pm - 8:50 am

GCM

MDW

20h 25m

2 stops

5:00 am - 12:55 pm

MDW

GCM

6h 55m

1 stop

$785Southwest

Sat, Feb 21 - Wed, Feb 25

1:25 pm - 8:50 am

GCM

MDW

20h 25m

2 stops

7:55 pm - 12:55 pm

MDW

GCM

16h 00m

2 stops

$801Southwest

Sat, Feb 21 - Wed, Feb 25

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

8h 10m

1 stop

MDW9:00 pmChicago Midway

Jan 26

MDW5:00 amChicago Midway

6h 55m

1 stop

GCM12:55 pmGeorge Town Owen Roberts Intl

$493

Southwest

Jan 22

GCM1:50 pmGeorge Town Owen Roberts Intl

8h 10m

1 stop

MDW9:00 pmChicago Midway

Jan 26

MDW7:50 pmChicago Midway

16h 05m

2 stops

GCM12:55 pmGeorge Town Owen Roberts Intl

$498

Southwest

Jan 22

GCM1:50 pmGeorge Town Owen Roberts Intl

9h 15m

2 stops

MDW10:05 pmChicago Midway

Jan 26

MDW7:55 pmChicago Midway

16h 00m

2 stops

GCM12:55 pmGeorge Town Owen Roberts Intl

$528

Delta flights from Cayman Islands to Chicago Midway Airport

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

Delta

Feb 21

GCM1:54 pmGeorge Town Owen Roberts Intl

9h 37m

1 stop

MDW10:31 pmChicago Midway

Feb 25

MDW6:00 amChicago Midway

5h 29m

1 stop

GCM12:29 pmGeorge Town Owen Roberts Intl

$474

Delta

Feb 25

GCM1:54 pmGeorge Town Owen Roberts Intl

9h 37m

1 stop

MDW10:31 pmChicago Midway

Mar 4

MDW6:00 amChicago Midway

5h 29m

1 stop

GCM12:29 pmGeorge Town Owen Roberts Intl

$523

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

Sat 2/21

1:54 pm-10:31 pm

1 stop9h 37m

Chicago Midway

Wed 2/25

6:00 am-12:29 pm

1 stop5h 29m

$474

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 2/25

1:54 pm-10:31 pm

1 stop9h 37m

Chicago Midway

Wed 3/4

6:00 am-12:29 pm

1 stop5h 29m

$523

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 6/11

12:45 pm-9:20 pm

1 stop8h 35m

Chicago Midway

Sun 6/14

8:40 pm-11:50 am

2 stops15h 10m

$602

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 6/11

12:45 pm-9:20 pm

1 stop8h 35m

Chicago Midway

Sun 6/14

5:20 am-11:50 am

1 stop6h 30m

$647

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

1:25 pm-8:50 am

2 stops20h 25m

Chicago Midway

Wed 2/25

5:00 am-12:55 pm

1 stop6h 55m

$785

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

1:25 pm-8:50 am

2 stops20h 25m

Chicago Midway

Wed 2/25

7:55 pm-12:55 pm

2 stops16h 00m

$801

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 3/8

4:45 pm-1:41 pm

1 stop20h 56m

$254

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sun 3/8

1:49 pm-1:08 pm

2 stops23h 19m

$322

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

8:50 am-9:29 pm

2 stops37h 39m

$340

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 2/21

8:50 am-10:25 pm

3 stops38h 35m

$357

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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?

Delta 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	8h 10m
Direct flights	None

The fastest flight from Cayman Islands to Chicago Midway Airport takes 8h 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

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

Schererville

Valparaiso

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.