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Cheap flights from Chicago Midway Airport to Grand Cayman from $146

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 3/12. 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
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
1 stop
Multiple Airlines Logo
7:00 am - 7:47 pm
GCM
-
MDW
12h 47m
2 stops
$467Multiple Airlines
Thu, Mar 12 - Thu, Mar 19
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 7:35 am
GCM
-
MDW
18h 30m
2 stops
$477Southwest
Tue, Apr 14 - Tue, Apr 28
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
1 stop
Multiple Airlines Logo
7:00 am - 1:41 pm
GCM
-
MDW
6h 41m
1 stop
$483Multiple Airlines
Thu, Mar 12 - Thu, Mar 19
Delta Logo
6:00 am - 11:47 am
MDW
-
GCM
5h 47m
1 stop
Delta Logo
1:12 pm - 10:31 pm
GCM
-
MDW
9h 19m
1 stop
$499Delta
Tue, Mar 31 - Tue, Apr 7
Multiple Airlines Logo
2:41 pm - 12:20 pm
MDW
-
GCM
21h 39m
2 stops
Multiple Airlines Logo
7:00 am - 1:41 pm
GCM
-
MDW
6h 41m
1 stop
$503Multiple Airlines
Fri, Mar 20 - Mon, Mar 23
Southwest Logo
8:55 pm - 12:10 pm
MDW
-
GCM
15h 15m
2 stops
Southwest Logo
1:05 pm - 9:25 pm
GCM
-
MDW
8h 20m
1 stop
$504Southwest
Tue, Apr 21 - Tue, Apr 28
Southwest Logo
9:35 pm - 12:10 pm
MDW
-
GCM
14h 35m
2 stops
Southwest Logo
1:05 pm - 9:50 pm
GCM
-
MDW
8h 45m
2 stops
$507Southwest
Thu, Apr 23 - Tue, Apr 28
Multiple Airlines Logo
9:04 pm - 9:15 pm
MDW
-
GCM
23h 11m
2 stops
Multiple Airlines Logo
7:00 am - 1:56 pm
GCM
-
MDW
7h 56m
1 stop
$508Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Multiple Airlines Logo
6:00 am - 11:35 am
MDW
-
GCM
29h 35m
1 stop
Multiple Airlines Logo
7:00 am - 1:41 pm
GCM
-
MDW
6h 41m
1 stop
$514Multiple Airlines
Sun, Mar 8 - Sun, Mar 15
Multiple Airlines Logo
3:45 pm - 11:35 am
MDW
-
GCM
19h 50m
2 stops
Multiple Airlines Logo
11:30 am - 1:41 pm
GCM
-
MDW
26h 11m
1 stop
$515Multiple Airlines
Sun, Mar 8 - Wed, Mar 11

Delta flights from Chicago Midway Airport to Grand Cayman

Our best Delta deals on Chicago Midway Airport to Grand Cayman flight tickets
Delta
Mar 31
MDW6:00 amChicago Midway
5h 47m
1 stop
GCM11:47 amGeorge Town Owen Roberts Intl
Apr 7
GCM1:12 pmGeorge Town Owen Roberts Intl
9h 19m
1 stop
MDW10:31 pmChicago Midway
$499
Delta
Apr 23
MDW6:00 amChicago Midway
6h 00m
1 stop
GCM12:00 pmGeorge Town Owen Roberts Intl
Apr 28
GCM1:25 pmGeorge Town Owen Roberts Intl
9h 03m
1 stop
MDW10:28 pmChicago Midway
$529
Delta
Apr 17
MDW6:00 amChicago Midway
6h 00m
1 stop
GCM12:00 pmGeorge Town Owen Roberts Intl
Apr 20
GCM1:25 pmGeorge Town Owen Roberts Intl
9h 03m
1 stop
MDW10:28 pmChicago Midway
$559

Southwest flights from Chicago Midway Airport to Grand Cayman

Our best Southwest deals on Chicago Midway Airport to Grand Cayman flight tickets
Southwest
Apr 14
MDW6:00 amChicago Midway
6h 10m
1 stop
GCM12:10 pmGeorge Town Owen Roberts Intl
Apr 28
GCM1:05 pmGeorge Town Owen Roberts Intl
18h 30m
2 stops
MDW7:35 amChicago Midway
$477
Southwest
Apr 21
MDW8:55 pmChicago Midway
15h 15m
2 stops
GCM12:10 pmGeorge Town Owen Roberts Intl
Apr 28
GCM1:05 pmGeorge Town Owen Roberts Intl
8h 20m
1 stop
MDW9:25 pmChicago Midway
$504
Southwest
Apr 23
MDW9:35 pmChicago Midway
14h 35m
2 stops
GCM12:10 pmGeorge Town Owen Roberts Intl
Apr 28
GCM1:05 pmGeorge Town Owen Roberts Intl
8h 45m
2 stops
MDW9:50 pmChicago Midway
$507

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 February 25, 2026.
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

Thu 3/12

6:00 am-9:15 pm

1 stop15h 15m

George Town Owen Roberts Intl

Thu 3/19

7:00 am-7:47 pm

2 stops12h 47m

$467

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 4/14

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Tue 4/28

1:05 pm-7:35 am

2 stops18h 30m

$477

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 3/12

6:00 am-9:15 pm

1 stop15h 15m

George Town Owen Roberts Intl

Thu 3/19

7:00 am-1:41 pm

1 stop6h 41m

$483

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/31

6:00 am-11:47 am

1 stop5h 47m

George Town Owen Roberts Intl

Tue 4/7

1:12 pm-10:31 pm

1 stop9h 19m

$499

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 3/20

2:41 pm-12:20 pm

2 stops21h 39m

George Town Owen Roberts Intl

Mon 3/23

7:00 am-1:41 pm

1 stop6h 41m

$503

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 4/21

8:55 pm-12:10 pm

2 stops15h 15m

George Town Owen Roberts Intl

Tue 4/28

1:05 pm-9:25 pm

1 stop8h 20m

$504

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 4/23

9:35 pm-12:10 pm

2 stops14h 35m

George Town Owen Roberts Intl

Tue 4/28

1:05 pm-9:50 pm

2 stops8h 45m

$507

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/1

9:04 pm-9:15 pm

2 stops23h 11m

George Town Owen Roberts Intl

Thu 3/5

7:00 am-1:56 pm

1 stop7h 56m

$508

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/8

6:00 am-11:35 am

1 stop29h 35m

George Town Owen Roberts Intl

Sun 3/15

7:00 am-1:41 pm

1 stop6h 41m

$514

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/8

3:45 pm-11:35 am

2 stops19h 50m

George Town Owen Roberts Intl

Wed 3/11

11:30 am-1:41 pm

1 stop26h 11m

$515

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 25m

Direct flights

None
The fastest flight from Chicago Midway Airport to Grand Cayman takes 5h 25m
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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