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Cheap flights from Chicago Midway Airport to Grand Cayman from $209

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 5/19. 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.
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:15 am
GCM
-
MDW
11h 10m
1 stop
$492Southwest
Tue, May 5 - Fri, May 8
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 11:55 pm
GCM
-
MDW
10h 50m
2 stops
$511Southwest
Tue, May 5 - Fri, May 8
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
7:00 am - 10:11 pm
GCM
-
MDW
15h 11m
2 stops
$523Multiple Airlines
Thu, Jun 4 - Thu, Jun 11
Southwest Logo
8:50 pm - 12:10 pm
MDW
-
GCM
15h 20m
2 stops
Southwest Logo
1:05 pm - 10:50 pm
GCM
-
MDW
9h 45m
2 stops
$542Southwest
Tue, May 5 - Fri, May 8
Delta Logo
6:05 am - 11:34 am
MDW
-
GCM
5h 29m
1 stop
Delta Logo
12:59 pm - 10:17 pm
GCM
-
MDW
9h 18m
1 stop
$553Delta
Sun, Jun 7 - Fri, Jun 12
Multiple Airlines Logo
3:20 pm - 12:45 pm
MDW
-
GCM
21h 25m
1 stop
Multiple Airlines Logo
4:45 pm - 10:11 pm
GCM
-
MDW
29h 26m
2 stops
$561Multiple Airlines
Mon, Jul 20 - Mon, Jul 27
Delta Logo
6:05 am - 11:34 am
MDW
-
GCM
5h 29m
1 stop
Delta Logo
12:59 pm - 10:17 pm
GCM
-
MDW
9h 18m
1 stop
$573Delta
Sun, Jun 7 - Fri, Jun 12
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:15 am
GCM
-
MDW
11h 10m
1 stop
$579Southwest
Tue, May 12 - Mon, May 18
Multiple Airlines Logo
6:00 am - 9:15 pm
MDW
-
GCM
15h 15m
2 stops
Multiple Airlines Logo
1:45 pm - 9:40 am
GCM
-
MDW
19h 55m
1 stop
$583Multiple Airlines
Mon, Jun 8 - Sat, Jun 13
Southwest Logo
6:00 am - 12:10 pm
MDW
-
GCM
6h 10m
1 stop
Southwest Logo
1:05 pm - 12:15 am
GCM
-
MDW
11h 10m
1 stop
$584Southwest
Tue, May 5 - Thu, May 7

Delta flights from Chicago Midway Airport to Grand Cayman

Our best Delta deals on Chicago Midway Airport to Grand Cayman flight tickets
Delta
Jun 7
MDW6:05 amChicago Midway
5h 29m
1 stop
GCM11:34 amGeorge Town Owen Roberts Intl
Jun 12
GCM12:59 pmGeorge Town Owen Roberts Intl
9h 18m
1 stop
MDW10:17 pmChicago Midway
$553
Delta
Jun 7
MDW6:05 amChicago Midway
5h 29m
1 stop
GCM11:34 amGeorge Town Owen Roberts Intl
Jun 12
GCM12:59 pmGeorge Town Owen Roberts Intl
9h 18m
1 stop
MDW10:17 pmChicago Midway
$573
Delta
Aug 16
MDW6:00 amChicago Midway
5h 41m
1 stop
GCM11:41 amGeorge Town Owen Roberts Intl
Aug 27
GCM12:56 pmGeorge Town Owen Roberts Intl
19h 46m
2 stops
MDW8:42 amChicago Midway
$602

Southwest flights from Chicago Midway Airport to Grand Cayman

Our best Southwest deals on Chicago Midway Airport to Grand Cayman flight tickets
Southwest
May 5
MDW6:00 amChicago Midway
6h 10m
1 stop
GCM12:10 pmGeorge Town Owen Roberts Intl
May 8
GCM1:05 pmGeorge Town Owen Roberts Intl
11h 10m
1 stop
MDW12:15 amChicago Midway
$492
Southwest
May 5
MDW6:00 amChicago Midway
6h 10m
1 stop
GCM12:10 pmGeorge Town Owen Roberts Intl
May 8
GCM1:05 pmGeorge Town Owen Roberts Intl
10h 50m
2 stops
MDW11:55 pmChicago Midway
$511
Southwest
May 5
MDW8:50 pmChicago Midway
15h 20m
2 stops
GCM12:10 pmGeorge Town Owen Roberts Intl
May 8
GCM1:05 pmGeorge Town Owen Roberts Intl
9h 45m
2 stops
MDW10:50 pmChicago Midway
$542

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 April 17, 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

Cheapest round-trip

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-12:15 am

1 stop11h 10m

$492

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-11:55 pm

2 stops10h 50m

$511

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 6/4

6:00 am-9:15 pm

2 stops15h 15m

George Town Owen Roberts Intl

Thu 6/11

7:00 am-10:11 pm

2 stops15h 11m

$523

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

8:50 pm-12:10 pm

2 stops15h 20m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-10:50 pm

2 stops9h 45m

$542
Quickest round-trip

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 6/7

6:05 am-11:34 am

1 stop5h 29m

George Town Owen Roberts Intl

Fri 6/12

12:59 pm-10:17 pm

1 stop9h 18m

$553

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 7/20

3:20 pm-12:45 pm

1 stop21h 25m

George Town Owen Roberts Intl

Mon 7/27

4:45 pm-10:11 pm

2 stops29h 26m

$561

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 6/7

6:05 am-11:34 am

1 stop5h 29m

George Town Owen Roberts Intl

Fri 6/12

12:59 pm-10:17 pm

1 stop9h 18m

$573

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/12

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Mon 5/18

1:05 pm-12:15 am

1 stop11h 10m

$579

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 6/8

6:00 am-9:15 pm

2 stops15h 15m

George Town Owen Roberts Intl

Sat 6/13

1:45 pm-9:40 am

1 stop19h 55m

$583

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 5/5

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Thu 5/7

1:05 pm-12:15 am

1 stop11h 10m

$584

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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See travel insights to Grand Cayman from

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 29m

Direct flights

None
The fastest flight from Chicago Midway Airport to Grand Cayman takes 5h 29m
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.
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Frequently asked questions about flying from Chicago Midway Airport to Grand Cayman

  • 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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Sun 5/17
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