Latest deals
Insights
FAQs
Price Alerts

Cheap flights from the Cayman Islands to Chicago from $315

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 12/29. 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

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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.
Delta Logo
1:50 pm - 11:47 pmGCM-MDW
10h 57m1 stop
Delta Logo
6:00 am - 2:27 pmMDW-GCM
7h 27m1 stop
$376Delta
Find Deal
Thu, Dec 18 - Thu, Dec 25
Southwest Logo
1:55 pm - 10:35 pmGCM-MDW
9h 40m1 stop
Southwest Logo
5:05 am - 12:35 pmMDW-GCM
6h 30m1 stop
$585Southwest
Find Deal
Sat, Dec 6 - Tue, Dec 9
Southwest Logo
1:55 pm - 7:55 pmGCM-MDW
7h 00m1 stop
Southwest Logo
6:00 pm - 12:35 pmMDW-GCM
17h 35m2 stops
$590Southwest
Find Deal
Sat, Dec 6 - Tue, Dec 9
Multiple Airlines Logo
2:50 pm - 10:05 amGCM-MDW
20h 15m1 stop
Multiple Airlines Logo
8:42 pm - 4:55 pmMDW-GCM
19h 13m2 stops
$613Multiple Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
Southwest Logo
1:30 pm - 7:35 pmGCM-MDW
7h 05m1 stop
Southwest Logo
5:50 am - 12:35 pmMDW-GCM
5h 45m1 stop
$712Southwest
Find Deal
Mon, Dec 8 - Fri, Dec 12
Southwest Logo
1:30 pm - 10:35 pmGCM-MDW
10h 05m2 stops
Southwest Logo
9:05 pm - 1:00 pmMDW-GCM
14h 55m2 stops
$741Southwest
Find Deal
Mon, Dec 8 - Fri, Dec 12

Delta flights from Cayman Islands to Chicago Midway Airport

Our best Delta deals on Cayman Islands to Chicago Midway Airport flight tickets
Delta
Dec 18
GCM1:50 pmGeorge Town Owen Roberts Intl
10h 57m
1 stop
MDW11:47 pmChicago Midway
Dec 25
MDW6:00 amChicago Midway
7h 27m
1 stop
GCM2:27 pmGeorge Town Owen Roberts Intl
$376
Find similar
Delta
Nov 7
GCM2:00 pmGeorge Town Owen Roberts Intl
9h 14m
1 stop
MDW10:14 pmChicago Midway
Nov 9
MDW6:00 amChicago Midway
5h 35m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
$505
Find similar

Southwest flights from Cayman Islands to Chicago Midway Airport

Our best Southwest deals on Cayman Islands to Chicago Midway Airport flight tickets
Southwest
Dec 6
GCM1:55 pmGeorge Town Owen Roberts Intl
9h 40m
1 stop
MDW10:35 pmChicago Midway
Dec 9
MDW5:05 amChicago Midway
6h 30m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
$585
Find similar
Southwest
Dec 6
GCM1:55 pmGeorge Town Owen Roberts Intl
7h 00m
1 stop
MDW7:55 pmChicago Midway
Dec 9
MDW6:00 pmChicago Midway
17h 35m
2 stops
GCM12:35 pmGeorge Town Owen Roberts Intl
$590
Find similar
Southwest
Nov 7
GCM1:40 pmGeorge Town Owen Roberts Intl
11h 30m
2 stops
MDW12:10 amChicago Midway
Nov 9
MDW5:50 amChicago Midway
5h 45m
1 stop
GCM12:35 pmGeorge Town Owen Roberts Intl
$617
Find similar

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 November 5, 2025.
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

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Thu 12/18

1:50 pm-11:47 pm

1 stop10h 57m

Chicago Midway

Thu 12/25

6:00 am-2:27 pm

1 stop7h 27m

$376

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 12/6

1:55 pm-10:35 pm

1 stop9h 40m

Chicago Midway

Tue 12/9

5:05 am-12:35 pm

1 stop6h 30m

$585

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Sat 12/6

1:55 pm-7:55 pm

1 stop7h 00m

Chicago Midway

Tue 12/9

6:00 pm-12:35 pm

2 stops17h 35m

$590

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 12/8

2:50 pm-10:05 am

1 stop20h 15m

Chicago Midway

Fri 12/12

8:42 pm-4:55 pm

2 stops19h 13m

$613

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 12/8

1:30 pm-7:35 pm

1 stop7h 05m

Chicago Midway

Fri 12/12

5:50 am-12:35 pm

1 stop5h 45m

$712

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 12/8

1:30 pm-10:35 pm

2 stops10h 05m

Chicago Midway

Fri 12/12

9:05 pm-1:00 pm

2 stops14h 55m

$741

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Mon 12/29

7:00 am-2:05 pm

1 stop8h 05m

$315

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Tue 11/25

11:30 am-6:20 pm

2 stops31h 50m

$324

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 11/26

1:30 pm-11:05 pm

2 stops10h 35m

$350

George TownChicago

GCM - MDW

GCMMDW

George Town Owen Roberts Intl

Wed 11/26

11:30 am-4:57 pm

1 stop6h 27m

$366

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

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

Direct flights

None
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

  • 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
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.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 12/5
Fri 12/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago