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Cheap flights from the Cayman Islands to Chicago from $376

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Cayman Islands to Chicago departing on 9/17. 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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0 bags

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Find the cheapest flights from the Cayman Islands to Chicago

Recent round-trip flight deals from the Cayman Islands to Chicago

Enter your travel dates to find the best prices.
Southwest Logo
12:50 pm - 9:25 pm
GCM
-
MDW
8h 35m
1 stop
Southwest Logo
8:45 pm - 12:05 pm
MDW
-
GCM
15h 20m
2 stops
$572Southwest
Mon, Jul 27 - Fri, Aug 14
Southwest Logo
12:50 pm - 11:00 pm
GCM
-
MDW
10h 10m
2 stops
Southwest Logo
8:45 pm - 12:05 pm
MDW
-
GCM
15h 20m
2 stops
$594Southwest
Mon, Jul 27 - Fri, Aug 14
Southwest Logo
1:05 pm - 10:25 pm
GCM
-
MDW
9h 20m
1 stop
Southwest Logo
5:10 pm - 10:30 am
MDW
-
GCM
17h 20m
2 stops
$617Southwest
Sat, Jun 20 - Fri, Jul 10
Southwest Logo
1:05 pm - 10:25 pm
GCM
-
MDW
9h 20m
1 stop
Southwest Logo
6:30 am - 11:55 am
MDW
-
GCM
5h 25m
1 stop
$641Southwest
Sat, Jun 20 - Fri, Jul 10
Delta Logo
12:56 pm - 12:38 pm
GCM
-
MDW
23h 42m
2 stops
Delta Logo
6:42 pm - 11:39 am
MDW
-
GCM
16h 57m
2 stops
$652Delta
Wed, Jul 29 - Tue, Aug 11
Southwest Logo
12:50 pm - 10:00 pm
GCM
-
MDW
9h 10m
1 stop
Southwest Logo
6:55 pm - 11:55 am
MDW
-
GCM
17h 00m
2 stops
$665Southwest
Wed, Jun 17 - Wed, Jun 24
Delta Logo
12:56 pm - 12:38 pm
GCM
-
MDW
23h 42m
2 stops
Delta Logo
6:05 am - 11:39 am
MDW
-
GCM
5h 34m
1 stop
$687Delta
Wed, Jul 29 - Fri, Aug 14
Delta Logo
12:56 pm - 9:08 am
GCM
-
MDW
20h 12m
2 stops
Delta Logo
9:24 am - 11:39 am
MDW
-
GCM
26h 15m
2 stops
$702Delta
Fri, Jul 24 - Mon, Aug 17
Multiple Airlines Logo
1:45 pm - 9:40 am
GCM
-
MDW
19h 55m
1 stop
Multiple Airlines Logo
6:05 am - 9:15 pm
MDW
-
GCM
15h 10m
2 stops
$752Multiple Airlines
Sat, Jul 25 - Mon, Aug 17
Delta Logo
12:56 pm - 10:15 pm
GCM
-
MDW
9h 19m
1 stop
Delta Logo
6:00 am - 11:31 am
MDW
-
GCM
5h 31m
1 stop
$762Delta
Tue, Jul 7 - Sat, Jul 11

Delta flights from Cayman Islands to Chicago Midway Airport

Our best Delta deals on Cayman Islands to Chicago Midway Airport flight tickets
Delta
Jul 29
GCM12:56 pmGeorge Town Owen Roberts Intl
23h 42m
2 stops
MDW12:38 pmChicago Midway
Aug 11
MDW6:42 pmChicago Midway
16h 57m
2 stops
GCM11:39 amGeorge Town Owen Roberts Intl
$652
Delta
Jul 29
GCM12:56 pmGeorge Town Owen Roberts Intl
23h 42m
2 stops
MDW12:38 pmChicago Midway
Aug 14
MDW6:05 amChicago Midway
5h 34m
1 stop
GCM11:39 amGeorge Town Owen Roberts Intl
$687
Delta
Jul 24
GCM12:56 pmGeorge Town Owen Roberts Intl
23h 42m
2 stops
MDW12:38 pmChicago Midway
Aug 11
MDW6:42 pmChicago Midway
16h 57m
2 stops
GCM11:39 amGeorge Town Owen Roberts Intl
$702

Southwest flights from Cayman Islands to Chicago Midway Airport

Our best Southwest deals on Cayman Islands to Chicago Midway Airport flight tickets
Southwest
Jul 27
GCM12:50 pmGeorge Town Owen Roberts Intl
8h 35m
1 stop
MDW9:25 pmChicago Midway
Aug 14
MDW8:45 pmChicago Midway
15h 20m
2 stops
GCM12:05 pmGeorge Town Owen Roberts Intl
$572
Southwest
Jul 27
GCM12:50 pmGeorge Town Owen Roberts Intl
10h 10m
2 stops
MDW11:00 pmChicago Midway
Aug 14
MDW8:45 pmChicago Midway
15h 20m
2 stops
GCM12:05 pmGeorge Town Owen Roberts Intl
$594
Southwest
Jun 20
GCM1:05 pmGeorge Town Owen Roberts Intl
9h 20m
1 stop
MDW10:25 pmChicago Midway
Jul 10
MDW5:10 pmChicago Midway
17h 20m
2 stops
GCM10:30 amGeorge Town Owen Roberts Intl
$617

momondo Fare Finder

 
Customize your flight search to find flights from Cayman Islands to Chicago Midway Airport 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 May 23, 2026.
Use the filters below to find and compare flights from the Cayman Islands to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 7/27

12:50 pm-9:25 pm

1 stop8h 35m

Chicago Midway

Fri 8/14

8:45 pm-12:05 pm

2 stops15h 20m

$572

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 7/27

12:50 pm-11:00 pm

2 stops10h 10m

Chicago Midway

Fri 8/14

8:45 pm-12:05 pm

2 stops15h 20m

$594

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 6/20

1:05 pm-10:25 pm

1 stop9h 20m

Chicago Midway

Fri 7/10

5:10 pm-10:30 am

2 stops17h 20m

$617
Quickest round-trip

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 6/20

1:05 pm-10:25 pm

1 stop9h 20m

Chicago Midway

Fri 7/10

6:30 am-11:55 am

1 stop5h 25m

$641

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 7/29

12:56 pm-12:38 pm

2 stops23h 42m

Chicago Midway

Tue 8/11

6:42 pm-11:39 am

2 stops16h 57m

$652

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 6/17

12:50 pm-10:00 pm

1 stop9h 10m

Chicago Midway

Wed 6/24

6:55 pm-11:55 am

2 stops17h 00m

$665

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 7/29

12:56 pm-12:38 pm

2 stops23h 42m

Chicago Midway

Fri 8/14

6:05 am-11:39 am

1 stop5h 34m

$687

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Fri 7/24

12:56 pm-9:08 am

2 stops20h 12m

Chicago Midway

Mon 8/17

9:24 am-11:39 am

2 stops26h 15m

$702

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 7/25

1:45 pm-9:40 am

1 stop19h 55m

Chicago Midway

Mon 8/17

6:05 am-9:15 pm

2 stops15h 10m

$752

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 7/7

12:56 pm-10:15 pm

1 stop9h 19m

Chicago Midway

Sat 7/11

6:00 am-11:31 am

1 stop5h 31m

$762

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

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 Cayman Islands to Chicago Midway?

Southwest and Delta are the most popular carriers operating from Cayman Islands to Chicago Midway

Cheap Cayman Islands to Chicago Midway Airport flight deals and tips

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

Fastest flight time

8h 35m

Direct flights

None
The fastest flight from Cayman Islands to Chicago Midway Airport takes 8h 35m
There are no direct flights from Cayman Islands to Chicago Midway Airport. There are no popular flight routes from Cayman Islands to Chicago Midway Airport.
Search flight deals

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

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

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

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

    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 Cayman Islands to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport 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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

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

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

Yes. momondo enables you to select and highlight flights to Chicago from Cayman Islands with this policy.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Cayman Islands.

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

Price alerts on flights to Chicago from Cayman Islands 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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