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Cheap flights from Chicago Midway Airport to Grand Cayman from $208

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 11/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago Midway Airport to Grand Cayman

Cheap round-trip flights

Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
Southwest Logo
1:30 pm - 8:35 pmGCM-MDW
8h 05m1 stop
$468Southwest
Find Deal
Mon, Dec 15 - Fri, Dec 19
Southwest Logo
6:00 pm - 12:35 pmMDW-GCM
17h 35m2 stops
Southwest Logo
1:30 pm - 9:45 pmGCM-MDW
9h 15m2 stops
$472Southwest
Find Deal
Mon, Dec 15 - Fri, Dec 19
Southwest Logo
5:25 am - 12:35 pmMDW-GCM
6h 10m1 stop
Southwest Logo
1:30 pm - 7:30 pmGCM-MDW
7h 00m1 stop
$520Southwest
Find Deal
Sun, Nov 30 - Fri, Dec 5
Southwest Logo
8:20 pm - 12:35 pmMDW-GCM
15h 15m2 stops
Southwest Logo
1:30 pm - 9:45 pmGCM-MDW
9h 15m2 stops
$524Southwest
Find Deal
Mon, Dec 15 - Fri, Dec 19
Delta Logo
6:00 am - 12:37 pmMDW-GCM
5h 37m1 stop
Delta Logo
1:55 pm - 10:05 pmGCM-MDW
9h 10m1 stop
$530Delta
Find Deal
Mon, Dec 15 - Fri, Dec 26
Southwest Logo
7:40 pm - 12:55 pmMDW-GCM
16h 15m2 stops
Southwest Logo
1:25 pm - 7:40 pmGCM-MDW
7h 15m1 stop
$542Southwest
Find Deal
Sat, Jan 10 - Sat, Jan 17
Delta Logo
6:00 am - 12:35 pmMDW-GCM
5h 35m1 stop
Delta Logo
2:00 pm - 9:46 pmGCM-MDW
8h 46m1 stop
$545Delta
Find Deal
Tue, Jan 13 - Sun, Jan 18
Delta Logo
6:00 am - 12:35 pmMDW-GCM
5h 35m1 stop
Delta Logo
2:00 pm - 9:46 pmGCM-MDW
8h 46m1 stop
$555Delta
Find Deal
Fri, Feb 6 - Fri, Feb 13
Logo
9:45 am - 5:20 pmMDW-GCM
7h 35m1 stop
Logo
1:45 pm - 10:05 amGCM-MDW
20h 20m1 stop
$558
Find Deal
Mon, Oct 20 - Sat, Oct 25
Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
Southwest Logo
1:30 pm - 8:35 pmGCM-MDW
8h 05m1 stop
$567Southwest
Find Deal
Tue, Dec 16 - Fri, Dec 26

Delta flights from Chicago Midway Airport to Grand Cayman

Our best Delta deals on Chicago Midway Airport to Grand Cayman flight tickets
Delta
Dec 15
MDW6:00 amChicago Midway
5h 37m
1 stop
GCM12:37 pmGeorge Town Owen Roberts Intl
Dec 26
GCM1:55 pmGeorge Town Owen Roberts Intl
9h 10m
1 stop
MDW10:05 pmChicago Midway
$530
Find similar
Delta
Jan 13
MDW6:00 amChicago Midway
5h 35m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Jan 18
GCM2:00 pmGeorge Town Owen Roberts Intl
8h 46m
1 stop
MDW9:46 pmChicago Midway
$545
Find similar
Delta
Feb 6
MDW6:00 amChicago Midway
5h 35m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Feb 13
GCM2:00 pmGeorge Town Owen Roberts Intl
8h 46m
1 stop
MDW9:46 pmChicago Midway
$555
Find similar

Southwest flights from Chicago Midway Airport to Grand Cayman

Our best Southwest deals on Chicago Midway Airport to Grand Cayman flight tickets
Southwest
Dec 15
MDW5:05 amChicago Midway
6h 30m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 19
GCM1:30 pmGeorge Town Owen Roberts Intl
8h 05m
1 stop
MDW8:35 pmChicago Midway
$468
Find similar
Southwest
Dec 15
MDW6:00 pmChicago Midway
17h 35m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 19
GCM1:30 pmGeorge Town Owen Roberts Intl
9h 15m
2 stops
MDW9:45 pmChicago Midway
$472
Find similar
Southwest
Nov 30
MDW5:25 amChicago Midway
6h 10m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Dec 5
GCM1:30 pmGeorge Town Owen Roberts Intl
7h 00m
1 stop
MDW7:30 pmChicago Midway
$520
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 August 27, 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

Mon 12/15

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

Fri 12/19

1:30 pm-8:35 pm

1 stop8h 05m

$468

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 12/15

6:00 pm-12:35 pm

2 stops17h 35m

George Town Owen Roberts Intl

Fri 12/19

1:30 pm-9:45 pm

2 stops9h 15m

$472

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 11/30

5:25 am-12:35 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 12/5

1:30 pm-7:30 pm

1 stop7h 00m

$520

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 12/15

8:20 pm-12:35 pm

2 stops15h 15m

George Town Owen Roberts Intl

Fri 12/19

1:30 pm-9:45 pm

2 stops9h 15m

$524

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 12/15

6:00 am-12:37 pm

1 stop5h 37m

George Town Owen Roberts Intl

Fri 12/26

1:55 pm-10:05 pm

1 stop9h 10m

$530

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 1/10

7:40 pm-12:55 pm

2 stops16h 15m

George Town Owen Roberts Intl

Sat 1/17

1:25 pm-7:40 pm

1 stop7h 15m

$542

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 1/13

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Sun 1/18

2:00 pm-9:46 pm

1 stop8h 46m

$545

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 2/6

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Fri 2/13

2:00 pm-9:46 pm

1 stop8h 46m

$555

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 10/20

9:45 am-5:20 pm

1 stop7h 35m

George Town Owen Roberts Intl

Sat 10/25

1:45 pm-10:05 am

1 stop20h 20m

$558

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 12/16

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

Fri 12/26

1:30 pm-8:35 pm

1 stop8h 05m

$567

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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

Direct flights

None
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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  • 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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