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Cheap flights from Chicago Midway Airport to the Cayman Islands from $198

1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Chicago Midway Airport to the Cayman Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:45 am - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 10m1 stop Orlando
Southwest Logo
1:50 pm - 10:50 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 00m1 stop Orlando
$474Southwest
Tue, Feb 2 - Wed, Feb 10
Southwest Logo
7:55 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
16h 00m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
1:50 pm - 10:25 amGCM  George Town Owen Roberts Intl-MDW Chicago Midway
21h 35m2 stops Orlando Denver Intl
$479Southwest
Tue, Feb 2 - Wed, Feb 10
Southwest Logo
7:55 pm - 12:55 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
16h 00m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
1:50 pm - 10:50 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 00m1 stop Orlando
$479Southwest
Tue, Feb 2 - Wed, Feb 10
Southwest Logo
5:20 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 15m1 stop Orlando
Southwest Logo
1:30 pm - 8:35 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
8h 05m1 stop Orlando
$519Southwest
Tue, Nov 3 - Fri, Nov 13
Southwest Logo
5:20 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 15m1 stop Orlando
Southwest Logo
4:10 pm - 11:00 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
7h 50m1 stop Baltimore/Washington
$523Southwest
Mon, Dec 14 - Sat, Dec 19
Southwest Logo
5:20 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 15m1 stop Orlando
Southwest Logo
4:10 pm - 11:00 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
7h 50m1 stop Baltimore/Washington
$523Southwest
Mon, Dec 14 - Sat, Dec 19
Southwest Logo
5:10 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 25m1 stop Orlando
Southwest Logo
1:50 pm - 11:00 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 10m2 stops Orlando Dallas Love Field
$523Southwest
Mon, Jan 4 - Mon, Jan 11
Southwest Logo
8:25 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
15h 10m2 stops Baltimore/Washington Orlando
Southwest Logo
1:50 pm - 11:00 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 10m2 stops Orlando Dallas Love Field
$523Southwest
Mon, Jan 4 - Mon, Jan 11
Southwest Logo
8:50 pm - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
14h 45m2 stops Phoenix Sky Harbor Intl Orlando
Southwest Logo
1:30 pm - 8:20 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
7h 50m2 stops Orlando Lambert-St Louis
$524Southwest
Tue, Nov 3 - Fri, Nov 13
Southwest Logo
5:20 am - 12:35 pmMDW  Chicago Midway-GCM George Town Owen Roberts Intl
6h 15m1 stop Orlando
Southwest Logo
1:30 pm - 11:05 pmGCM  George Town Owen Roberts Intl-MDW Chicago Midway
10h 35m2 stops Orlando Baltimore/Washington
$524Southwest
Tue, Nov 3 - Fri, Nov 13

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Delta flights from Chicago Midway Airport to Cayman Islands

Our best Delta deals on Chicago Midway Airport to Cayman Islands flight tickets
Delta
Jan 3
MDW6:00 amChicago Midway
7h 30m
1 stop
GCM2:30 pmGeorge Town Owen Roberts Intl
Jan 13
GCM2:05 pmGeorge Town Owen Roberts Intl
9h 05m
1 stop
MDW10:10 pmChicago Midway
$631
Delta
Jan 3
MDW6:00 amChicago Midway
7h 30m
1 stop
GCM2:30 pmGeorge Town Owen Roberts Intl
Jan 13
GCM2:05 pmGeorge Town Owen Roberts Intl
9h 05m
1 stop
MDW10:10 pmChicago Midway
$656
Delta
Nov 14
MDW6:00 amChicago Midway
5h 25m
1 stop
GCM12:25 pmGeorge Town Owen Roberts Intl
Nov 21
GCM1:50 pmGeorge Town Owen Roberts Intl
10h 06m
1 stop
MDW10:56 pmChicago Midway
$681

Southwest flights from Chicago Midway Airport to Cayman Islands

Our best Southwest deals on Chicago Midway Airport to Cayman Islands flight tickets
Southwest
Feb 2
MDW5:45 amChicago Midway
6h 10m
1 stop
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 10
GCM1:50 pmGeorge Town Owen Roberts Intl
10h 00m
1 stop
MDW10:50 pmChicago Midway
$474
Southwest
Feb 2
MDW7:55 pmChicago Midway
16h 00m
2 stops
GCM12:55 pmGeorge Town Owen Roberts Intl
Feb 10
GCM1:50 pmGeorge Town Owen Roberts Intl
21h 35m
2 stops
MDW10:25 amChicago Midway
$479
Southwest
Nov 3
MDW5:20 amChicago Midway
6h 15m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
Nov 13
GCM1:30 pmGeorge Town Owen Roberts Intl
8h 05m
1 stop
MDW8:35 pmChicago Midway
$519

momondo Fare Finder

 
Use the filters below to find and compare flights from Chicago Midway Airport to the Cayman Islands that are best for you.

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Route

Depart

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Price

Cheapest round-trip

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Tue 2/2

5:45 am-12:55 pm

1 stop6h 10m

George Town Owen Roberts Intl

Wed 2/10

1:50 pm-10:50 pm

1 stop10h 00m

$474

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Tue 2/2

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

Wed 2/10

1:50 pm-10:25 am

2 stops21h 35m

$479

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Tue 2/2

7:55 pm-12:55 pm

2 stops16h 00m

George Town Owen Roberts Intl

Wed 2/10

1:50 pm-10:50 pm

1 stop10h 00m

$479

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Tue 11/3

5:20 am-12:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

Fri 11/13

1:30 pm-8:35 pm

1 stop8h 05m

$519
Quickest round-trip

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Mon 12/14

5:20 am-12:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

Sat 12/19

4:10 pm-11:00 pm

1 stop7h 50m

$523

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Mon 12/14

5:20 am-12:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

Sat 12/19

4:10 pm-11:00 pm

1 stop7h 50m

$523

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Mon 1/4

5:10 am-12:35 pm

1 stop6h 25m

George Town Owen Roberts Intl

Mon 1/11

1:50 pm-11:00 pm

2 stops10h 10m

$523

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Mon 1/4

8:25 pm-12:35 pm

2 stops15h 10m

George Town Owen Roberts Intl

Mon 1/11

1:50 pm-11:00 pm

2 stops10h 10m

$523

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Tue 11/3

8:50 pm-12:35 pm

2 stops14h 45m

George Town Owen Roberts Intl

Fri 11/13

1:30 pm-8:20 pm

2 stops7h 50m

$524

ChicagoGeorge Town

MDW Chicago Midway - GCM George Town Owen Roberts Intl

MDWGCM

Chicago Midway

Tue 11/3

5:20 am-12:35 pm

1 stop6h 15m

George Town Owen Roberts Intl

Fri 11/13

1:30 pm-11:05 pm

2 stops10h 35m

$524

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 resultsSorted by cheapest first
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See travel insights to the Cayman Islands from

How to get the cheapest flight ticket from Chicago Midway Airport to Cayman Islands

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 Chicago Midway to Cayman Islands?

Southwest is the most popular carrier operating from Chicago Midway to Cayman Islands

Cheap Chicago Midway Airport to Cayman Islands flight deals and tips

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

Best Price Found

$198

Fastest flight time

5h 25m

Direct flights

None
The best one-way flight to Cayman Islands from Chicago Midway Airport in the past 72 hours is $198. The best round-trip flight deal from Chicago Midway Airport to Cayman Islands found on momondo in the last 72 hours is $474.
The fastest flight from Chicago Midway Airport to Cayman Islands takes 5h 25m
There are no direct flights from Chicago Midway Airport to Cayman Islands. There are no popular flight routes from Chicago Midway Airport to Cayman Islands.
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to the Cayman Islands

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

    Prices for flights from Chicago Midway Airport to Cayman Islands are updated daily.

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

    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 Chicago Midway Airport to Cayman Islands.

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

    The travel and health documents required for your trip to Cayman Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Cayman Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Why use momondo?

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

Finding the right flight to Cayman Islands from Chicago 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 Cayman Islands quick and easy, saving you time and money.

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

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

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

Once you have performed a search for Chicago to Cayman Islands flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

Yes momondo offers price alerts on flights to Cayman Islands from Chicago. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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