HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Islands

$168+ Cheap flights from Chicago (CHI) to the Cayman Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
avr. 7 — avr. 141
lun. 4/7
lun. 4/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Cayman Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Chicago to Cayman Islands

Keep the following information in mind while searching for Chicago to Cayman Islands flight deals. Data was last updated avril 2, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$492
(Mytrip)

One-way from

$168
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$641

Good round-trip deal

$735 or less

Good one-way deal

$453 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Chicago (CHI) to Cayman Islands
Search Deals
One-way flight from Chicago (CHI) to Cayman Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($62 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2025
Search Deals
Price to beat on a round-trip flight from Chicago (CHI) to Cayman Islands.
Search Deals
Price to beat on a one-way flight from Chicago (CHI) to Cayman Islands.
Search Deals

Find flight deals from Chicago to Cayman Islands

Cheapest flights from Chicago to Cayman Islands
Explore the most affordable flight options available from Chicago to Cayman Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on avril 2, 2025.

This Mytrip deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/35:55 amORD - GCM
2 stops29h 45mMultiple Airlines
sam. 5/108:50 amGCM - ORD
1 stop8h 51mMultiple Airlines
Deal found 4/1$492
This Air Canada deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
jeu. 6/512:50 pmGCM - ORD
2 stops21h 02mAir Canada
Deal found 4/1$518
This Kiwi.com deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/14:00 pmMDW - GCM
1 stop23h 45mMultiple Airlines
jeu. 5/812:40 pmGCM - MDW
1 stop10h 00mMultiple Airlines
Deal found 4/1$522
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/125:05 amMDW - GCM
1 stop6h 30mSouthwest
dim. 11/161:30 pmGCM - MDW
2 stops12h 20mSouthwest
Deal found 3/31$602
This American Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 5/285:00 amORD - GCM
1 stop6h 20mAmerican Airlines
mar. 6/32:10 pmGCM - ORD
2 stops10h 01mAmerican Airlines
Deal found 4/1$614
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/155:30 amORD - GCM
1 stop5h 50mDelta
jeu. 5/2212:35 pmGCM - ORD
1 stop8h 45mDelta
Deal found 4/1$635
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 8/306:00 amMDW - GCM
1 stop5h 31mDelta
jeu. 9/412:50 pmGCM - MDW
1 stop8h 57mDelta
Deal found 4/2$635
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 5/39:26 amORD - GCM
Nonstop4h 04mUnited Airlines
sam. 5/101:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/1$645
This WestJet deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 7/315:30 pmORD - GCM
2 stops43h 15mWestJet
mar. 8/51:45 pmGCM - ORD
2 stops26h 59mWestJet
Deal found 4/1$885

Cheapflights Fare Finder

Customize your flight search to find flights from Chicago to Cayman Islands 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, Cheapflights users made 2,558,603 searches. Data last updated avril 2, 2025.
Use the filters below to find and compare flights from Chicago to the Cayman Islands that are best for you.

Fly from

Chicago

Fly to

Cayman Islands

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sam. 5/3

5:55 am-11:40 am

2 stops29h 45m

George Town Owen Roberts Intl

sam. 5/10

8:50 am-5:41 pm

1 stop8h 51m

$492

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dim. 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

jeu. 6/5

12:50 pm-9:52 am

2 stops21h 02m

$518

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jeu. 5/1

4:00 pm-3:45 pm

1 stop23h 45m

George Town Owen Roberts Intl

jeu. 5/8

12:40 pm-10:40 pm

1 stop10h 00m

$522

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mer. 5/28

5:00 am-11:20 am

1 stop6h 20m

George Town Owen Roberts Intl

mar. 6/3

2:10 pm-12:11 am

2 stops10h 01m

$614

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

ven. 6/13

5:00 am-11:50 am

1 stop6h 50m

George Town Owen Roberts Intl

mar. 6/17

12:45 pm-7:25 pm

1 stop6h 40m

$616

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jeu. 5/15

5:30 am-11:20 am

1 stop5h 50m

George Town Owen Roberts Intl

jeu. 5/22

12:35 pm-9:20 pm

1 stop8h 45m

$635

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sam. 8/30

6:00 am-11:31 am

1 stop5h 31m

George Town Owen Roberts Intl

jeu. 9/4

12:50 pm-9:47 pm

1 stop8h 57m

$635

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sam. 5/3

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

sam. 5/10

1:45 pm-6:07 pm

Nonstop4h 22m

$645

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jeu. 7/31

5:30 pm-12:45 pm

2 stops43h 15m

George Town Owen Roberts Intl

mar. 8/5

1:45 pm-4:44 pm

2 stops26h 59m

$885

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jeu. 5/1

4:00 pm-3:45 pm

1 stop23h 45m

$206

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/1

Showing 1-10 of 19 results
1
2

Best time to book a flight from Chicago to Cayman Islands

Have a flexible travel schedule? Discover the best time to fly to Cayman Islands from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Chicago to the Cayman Islands

What is the cheapest month to book a flight from Chicago to Cayman Islands?

Currently, January is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $467). Flying from Chicago to Cayman Islands in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to KY?

Find hourly flight availability from Chicago to Cayman Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated avril 2, 2025.

When flying from Chicago to Cayman Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Cayman Islands

Get insights into the airlines that provide service to Cayman Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Cayman Islands. Reviews last updated avril 2, 2025.
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
WestJet
7.2
Good
2,789 reviews
Southwest
8.0
Very good
4,272 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Cayman Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Chicago to Cayman Islands one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $213. However, be on the lookout for offers from Southwest and Delta, as they are both options that can get you from Chicago to Cayman Islands for a low price.

  • What are the most popular routes from Chicago to Cayman Islands?

    When deciding which route to take from Chicago to Cayman Islands consider Chicago O'Hare Intl - George Town Owen Roberts Intl, Chicago Midway - George Town Owen Roberts Intl or Chicago O'Hare Intl - Cayman Brac Gerrard-Smith as they are the most popular.

  • What are the cheapest flights from Chicago to Cayman Islands?

    On average you can expect to pay $717 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $313 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $470.

  • Can I find deals for flights from Chicago to Cayman Islands that include hotel bookings?

    Yes. In addition to deals on Chicago to Cayman Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Cayman Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Cayman Islands.

  • Can I find deals for business class flights from Chicago to Cayman Islands?

    Yes. Cheapflights offers flight deals from Chicago to Cayman Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Cayman Islands?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Cayman Islands (average of $467). Flying from Chicago to Cayman Islands in March is currently the most expensive (average of $594). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Montego Bay flights
O'Hare Intl to Oranjestad flights
Midway to Punta Cana flights
Midway to Montego Bay flights
O'Hare Intl to Nassau flights
O'Hare Intl to Saint Thomas Island flights
Midway to Oranjestad flights
St. Louis to Luis Munoz Marin Intl flights
O'Hare Intl to Simpson Bay flights
O'Hare Intl to Santo Domingo flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Castries flights
St. Louis to Punta Cana flights
O'Hare Intl to Christiansted flights
Midway to Nassau flights
St. Louis to Saint Thomas Island flights
O'Hare Intl to George Town flights
St. Louis to Montego Bay flights
O'Hare Intl to Puerto Plata flights
Midway to Saint Thomas Island flights
Midway to Santo Domingo flights
O'Hare Intl to Providenciales flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Kingston flights
O'Hare Intl to Ponce flights
St. Louis to Nassau flights
Midway to Providenciales flights
St. Louis to Providenciales flights
Moline to Montego Bay flights
St. Louis to Oranjestad flights
St. Louis to George Town flights
St. Louis to Christiansted flights
O'Hare Intl to Road Town flights
Midway to Simpson Bay flights
St. Louis to Castries flights
O'Hare Intl to St. John's flights
O'Hare Intl to Gregory Town flights
Midway to George Town flights
O'Hare Intl to Santiago de los Caballeros flights
O'Hare Intl to Port of Spain flights
St. Louis to Simpson Bay flights
O'Hare Intl to Basseterre flights
O'Hare Intl to St. George's flights
Moline to Punta Cana flights
O'Hare Intl to Freeport flights
O'Hare Intl to Castries flights
St. Louis to Willemstad flights

Top 3 airlines flying from Chicago to Cayman Islands

Discover the top 3 airlines that operate flights from Chicago to Cayman Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated avril 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$660FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$504Average$702FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.