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Cheap flights from Chicago Midway Airport to Grand Cayman from $151

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Grand Cayman departing on 1/10. 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
0 bags

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Find the cheapest flights from Chicago Midway Airport to Grand Cayman

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
2:24 pm - 11:35 am
MDW
-
GCM
20h 11m1 stop
Multiple Airlines Logo
11:30 am - 10:17 pm
GCM
-
MDW
11h 47m2 stops
$395Multiple Airlines
Sat, Jan 3 - Wed, Jan 7
Multiple Airlines Logo
6:10 am - 9:15 pm
MDW
-
GCM
14h 05m2 stops
Multiple Airlines Logo
7:00 am - 6:54 pm
GCM
-
MDW
12h 54m1 stop
$409Multiple Airlines
Fri, Jan 9 - Fri, Jan 16
Southwest Logo
7:50 pm - 12:55 pm
MDW
-
GCM
16h 05m2 stops
Southwest Logo
1:50 pm - 10:05 pm
GCM
-
MDW
9h 15m2 stops
$411Southwest
Mon, Jan 26 - Fri, Jan 30
Multiple Airlines Logo
3:01 pm - 11:35 am
MDW
-
GCM
19h 34m1 stop
Multiple Airlines Logo
7:00 am - 2:06 pm
GCM
-
MDW
8h 06m1 stop
$422Multiple Airlines
Wed, Jan 7 - Fri, Jan 9
Multiple Airlines Logo
3:32 pm - 11:35 am
MDW
-
GCM
19h 03m1 stop
Multiple Airlines Logo
11:30 am - 10:17 pm
GCM
-
MDW
11h 47m2 stops
$433Multiple Airlines
Wed, Dec 31 - Wed, Jan 7
Multiple Airlines Logo
6:15 am - 9:15 pm
MDW
-
GCM
14h 00m1 stop
Multiple Airlines Logo
11:30 am - 1:56 pm
GCM
-
MDW
27h 26m1 stop
$442Multiple Airlines
Thu, Feb 26 - Wed, Mar 4
Southwest Logo
5:05 am - 11:55 am
MDW
-
GCM
6h 50m1 stop
Southwest Logo
1:05 pm - 9:25 pm
GCM
-
MDW
8h 20m1 stop
$446Southwest
Sun, Apr 26 - Wed, Apr 29
Southwest Logo
9:50 pm - 12:10 pm
MDW
-
GCM
14h 20m2 stops
Southwest Logo
1:05 pm - 9:50 pm
GCM
-
MDW
8h 45m2 stops
$451Southwest
Sun, Apr 26 - Wed, Apr 29
Delta Logo
6:00 am - 12:40 pm
MDW
-
GCM
5h 40m1 stop
Delta Logo
2:05 pm - 10:22 pm
GCM
-
MDW
9h 17m1 stop
$452Delta
Wed, Feb 4 - Thu, Feb 5
Multiple Airlines Logo
2:24 pm - 11:35 am
MDW
-
GCM
20h 11m1 stop
Multiple Airlines Logo
7:00 am - 2:06 pm
GCM
-
MDW
8h 06m1 stop
$455Multiple Airlines
Sat, Jan 3 - Fri, Jan 9

Southwest flights from Chicago Midway Airport to Grand Cayman

Our best Southwest deals on Chicago Midway Airport to Grand Cayman flight tickets
Southwest
Jan 26
MDW7:50 pmChicago Midway
16h 05m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Jan 30
GCM1:50 pmGeorge Town Owen Roberts Intl
9h 15m
2 stops
MDW10:05 pmChicago Midway
$411
Find similar
Southwest
Apr 26
MDW5:05 amChicago Midway
6h 50m
1 stop
GCM11:55 amGeorge Town Owen Roberts Intl
Apr 29
GCM1:05 pmGeorge Town Owen Roberts Intl
8h 20m
1 stop
MDW9:25 pmChicago Midway
$446
Find similar
Southwest
Apr 26
MDW9:50 pmChicago Midway
14h 20m
2 stops
GCM12:10 pmGeorge Town Owen Roberts Intl
Apr 29
GCM1:05 pmGeorge Town Owen Roberts Intl
8h 45m
2 stops
MDW9:50 pmChicago Midway
$451
Find similar

Delta flights from Chicago Midway Airport to Grand Cayman

Our best Delta deals on Chicago Midway Airport to Grand Cayman flight tickets
Delta
Feb 4
MDW6:00 amChicago Midway
5h 40m
1 stop
GCM12:40 pmGeorge Town Owen Roberts Intl
Feb 5
GCM2:05 pmGeorge Town Owen Roberts Intl
9h 17m
1 stop
MDW10:22 pmChicago Midway
$452
Find similar
Delta
Jan 11
MDW6:30 pmChicago Midway
17h 10m
2 stops
GCM12:40 pmGeorge Town Owen Roberts Intl
Jan 16
GCM2:05 pmGeorge Town Owen Roberts Intl
19h 47m
2 stops
MDW8:52 amChicago Midway
$457
Find similar
Delta
Jan 10
MDW6:45 amChicago Midway
6h 15m
1 stop
GCM2:00 pmGeorge Town Owen Roberts Intl
Jan 14
GCM2:05 pmGeorge Town Owen Roberts Intl
9h 02m
1 stop
MDW10:07 pmChicago Midway
$482
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Grand Cayman 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 December 11, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 1/3

2:24 pm-11:35 am

1 stop20h 11m

George Town Owen Roberts Intl

Wed 1/7

11:30 am-10:17 pm

2 stops11h 47m

$395

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 1/9

6:10 am-9:15 pm

2 stops14h 05m

George Town Owen Roberts Intl

Fri 1/16

7:00 am-6:54 pm

1 stop12h 54m

$409

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/26

7:50 pm-12:55 pm

2 stops16h 05m

George Town Owen Roberts Intl

Fri 1/30

1:50 pm-10:05 pm

2 stops9h 15m

$411

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 1/7

3:01 pm-11:35 am

1 stop19h 34m

George Town Owen Roberts Intl

Fri 1/9

7:00 am-2:06 pm

1 stop8h 06m

$422

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/31

3:32 pm-11:35 am

1 stop19h 03m

George Town Owen Roberts Intl

Wed 1/7

11:30 am-10:17 pm

2 stops11h 47m

$433

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 2/26

6:15 am-9:15 pm

1 stop14h 00m

George Town Owen Roberts Intl

Wed 3/4

11:30 am-1:56 pm

1 stop27h 26m

$442

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/26

5:05 am-11:55 am

1 stop6h 50m

George Town Owen Roberts Intl

Wed 4/29

1:05 pm-9:25 pm

1 stop8h 20m

$446

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/26

9:50 pm-12:10 pm

2 stops14h 20m

George Town Owen Roberts Intl

Wed 4/29

1:05 pm-9:50 pm

2 stops8h 45m

$451

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 2/4

6:00 am-12:40 pm

1 stop5h 40m

George Town Owen Roberts Intl

Thu 2/5

2:05 pm-10:22 pm

1 stop9h 17m

$452

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 1/3

2:24 pm-11:35 am

1 stop20h 11m

George Town Owen Roberts Intl

Fri 1/9

7:00 am-2:06 pm

1 stop8h 06m

$455

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago Midway Airport to Grand Cayman

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

Can stopping save me money on Chicago Midway Airport to Grand Cayman flights?

No. A direct flight is the cheapest option for a flight between Chicago Midway Airport to Grand Cayman.

Cheap Chicago Midway Airport to Grand Cayman flight deals and tips

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

Fastest flight time

5h 24m

Direct flights

None
The fastest flight from Chicago Midway Airport to Grand Cayman takes 5h 24m
There are no direct flights from Chicago Midway Airport to Grand Cayman. There are no popular flight routes from Chicago Midway Airport to Grand Cayman.
Search flight deals

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

    Prices for flights from Chicago Midway Airport to Grand Cayman were last updated today.

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

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago Midway Airport to Grand Cayman.

  • What documentation or ID do you need to fly to Grand Cayman?

    The necessary travel and health documents for your Grand Cayman 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.

  • What is the most popular plane model from Chicago Midway Airport to Grand Cayman?

Why use momondo?

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

It is quick and easy to find Chicago to Grand Cayman flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Grand Cayman that suits you.

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

All flight searches from Chicago to Grand Cayman on momondo can be filtered to show those which offer flexible booking policies.

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

momondo provides multiple filters to help you find the best flight to Grand Cayman from Chicago. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

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

Price alerts on flights to Grand Cayman from Chicago 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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Sat 1/10
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