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Cheap flights from the Cayman Islands to Chicago from $318

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Cayman Islands to Chicago departing on 8/21. 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 the Cayman Islands to Chicago

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

Enter your travel dates to find the best prices.
Southwest Logo
1:30 pm - 11:05 pm
GCM
-
MDW
10h 35m
2 stops
Southwest Logo
6:05 pm - 12:35 pm
MDW
-
GCM
17h 30m
2 stops
$486Southwest
Fri, Nov 6 - Mon, Nov 9
Southwest Logo
1:30 pm - 11:05 pm
GCM
-
MDW
10h 35m
2 stops
Southwest Logo
5:10 am - 12:35 pm
MDW
-
GCM
6h 25m
1 stop
$518Southwest
Fri, Nov 6 - Mon, Nov 9
Southwest Logo
1:30 pm - 6:55 pm
GCM
-
MDW
6h 25m
1 stop
Southwest Logo
5:10 am - 12:35 pm
MDW
-
GCM
6h 25m
1 stop
$545Southwest
Fri, Nov 6 - Mon, Nov 9
Delta Logo
1:04 pm - 10:36 pm
GCM
-
MDW
9h 32m
1 stop
Delta Logo
6:05 am - 11:39 am
MDW
-
GCM
5h 34m
1 stop
$672Delta
Tue, Aug 4 - Tue, Aug 11
Delta Logo
12:56 pm - 10:15 pm
GCM
-
MDW
9h 19m
1 stop
Delta Logo
6:42 pm - 11:39 am
MDW
-
GCM
16h 57m
2 stops
$759Delta
Sat, Aug 1 - Sat, Aug 8
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
Southwest Logo
7:30 pm - 12:55 pm
MDW
-
GCM
16h 25m
2 stops
$779Southwest
Thu, Dec 31 - Wed, Jan 6
Southwest Logo
1:30 pm - 10:40 pm
GCM
-
MDW
10h 10m
2 stops
Southwest Logo
5:45 am - 12:55 pm
MDW
-
GCM
6h 10m
1 stop
$811Southwest
Thu, Dec 31 - Wed, Jan 6
Delta Logo
12:56 pm - 10:15 pm
GCM
-
MDW
9h 19m
1 stop
Delta Logo
6:05 am - 11:39 am
MDW
-
GCM
5h 34m
1 stop
$847Delta
Fri, Jul 31 - Wed, Aug 5
Delta Logo
3:50 pm - 10:10 pm
GCM
-
MDW
7h 20m
1 stop
Delta Logo
6:00 am - 12:40 pm
MDW
-
GCM
5h 40m
1 stop
$912Delta
Thu, Dec 31 - Wed, Jan 6
Delta Logo
12:55 pm - 10:25 pm
GCM
-
MDW
9h 30m
1 stop
Delta Logo
6:45 pm - 11:40 am
MDW
-
GCM
16h 55m
2 stops
$932Delta
Thu, Oct 8 - Wed, Oct 14

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Delta flights from Cayman Islands to Chicago Midway Airport

Our best Delta deals on Cayman Islands to Chicago Midway Airport flight tickets
Delta
Aug 1
GCM12:56 pmGeorge Town Owen Roberts Intl
9h 19m
1 stop
MDW10:15 pmChicago Midway
Aug 8
MDW6:42 pmChicago Midway
16h 57m
2 stops
GCM11:39 amGeorge Town Owen Roberts Intl
$759
Delta
Jul 31
GCM12:56 pmGeorge Town Owen Roberts Intl
9h 19m
1 stop
MDW10:15 pmChicago Midway
Aug 5
MDW6:05 amChicago Midway
5h 34m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
$847
Delta
Oct 8
GCM12:55 pmGeorge Town Owen Roberts Intl
9h 30m
1 stop
MDW10:25 pmChicago Midway
Oct 14
MDW6:45 pmChicago Midway
16h 55m
2 stops
GCM11:40 amGeorge Town Owen Roberts Intl
$932

Southwest flights from Cayman Islands to Chicago Midway Airport

Our best Southwest deals on Cayman Islands to Chicago Midway Airport flight tickets
Southwest
Nov 6
GCM1:30 pmGeorge Town Owen Roberts Intl
10h 35m
2 stops
MDW11:05 pmChicago Midway
Nov 9
MDW6:05 pmChicago Midway
17h 30m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
$486
Southwest
Nov 6
GCM1:30 pmGeorge Town Owen Roberts Intl
10h 35m
2 stops
MDW11:05 pmChicago Midway
Nov 9
MDW5:10 amChicago Midway
6h 25m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
$518
Southwest
Nov 6
GCM1:30 pmGeorge Town Owen Roberts Intl
6h 25m
1 stop
MDW6:55 pmChicago Midway
Nov 9
MDW5:10 amChicago Midway
6h 25m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
$545

momondo Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Chicago Midway Airport 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 8, 2026.
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 - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 11/6

1:30 pm-11:05 pm

2 stops10h 35m

Chicago Midway

Mon 11/9

6:05 pm-12:35 pm

2 stops17h 30m

$486

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 11/6

1:30 pm-11:05 pm

2 stops10h 35m

Chicago Midway

Mon 11/9

5:10 am-12:35 pm

1 stop6h 25m

$518
Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 11/6

1:30 pm-6:55 pm

1 stop6h 25m

Chicago Midway

Mon 11/9

5:10 am-12:35 pm

1 stop6h 25m

$545

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 8/4

1:04 pm-10:36 pm

1 stop9h 32m

Chicago Midway

Tue 8/11

6:05 am-11:39 am

1 stop5h 34m

$672

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 8/1

12:56 pm-10:15 pm

1 stop9h 19m

Chicago Midway

Sat 8/8

6:42 pm-11:39 am

2 stops16h 57m

$759

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/31

1:30 pm-10:40 pm

2 stops10h 10m

Chicago Midway

Wed 1/6

7:30 pm-12:55 pm

2 stops16h 25m

$779

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/31

1:30 pm-10:40 pm

2 stops10h 10m

Chicago Midway

Wed 1/6

5:45 am-12:55 pm

1 stop6h 10m

$811

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 7/31

12:56 pm-10:15 pm

1 stop9h 19m

Chicago Midway

Wed 8/5

6:05 am-11:39 am

1 stop5h 34m

$847

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/31

3:50 pm-10:10 pm

1 stop7h 20m

Chicago Midway

Wed 1/6

6:00 am-12:40 pm

1 stop5h 40m

$912

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 10/8

12:55 pm-10:25 pm

1 stop9h 30m

Chicago Midway

Wed 10/14

6:45 pm-11:40 am

2 stops16h 55m

$932

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 Chicago from

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

Fastest flight time

9h 19m

Direct flights

None
The fastest flight from Cayman Islands to Chicago Midway Airport takes 9h 19m
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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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.

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