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Cayman Islands

$178+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
abr. 27 — may. 41
dom. 4/27
dom. 5/4
1 adult, Economy
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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 abril 22, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$491
(Air Canada)

One-way from

$185
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$648

Good round-trip deal

$670 or less

Good one-way deal

$313 or less
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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From Chicago (CHI) to Cayman Islands
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One-way flight from Chicago (CHI) to Cayman Islands
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Highest demand for flights based on searches. 8% potential increase in price ($62 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Chicago (CHI) to Cayman Islands.
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Price to beat on a one-way flight from Chicago (CHI) to Cayman Islands.
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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 abril 22, 2025.

This Air Canada deal was found by Cheapflights users on 4/22. 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.
dom. 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
jue. 6/512:50 pmGCM - ORD
1 stop19h 09mAir Canada
Deal found 4/22$491
This Mytrip deal was found by Cheapflights users on 4/22. 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.
mar. 5/67:00 pmORD - GCM
1 stop21h 10mMultiple Airlines
vie. 5/94:45 pmGCM - ORD
2 stops27h 22mMultiple Airlines
Deal found 4/22$492
This Southwest deal was found by Cheapflights users on 4/22. 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.
lun. 11/175:05 amMDW - GCM
1 stop6h 30mSouthwest
sáb. 11/223:40 pmGCM - MDW
1 stop8h 40mSouthwest
Deal found 4/22$538
This Southwest deal was found by Cheapflights users on 4/22. 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.
lun. 11/174:25 pmORD - GCM
2 stops19h 10mSouthwest
sáb. 11/222:15 pmGCM - ORD
1 stop8h 35mSouthwest
Deal found 4/22$576
This Delta deal was found by Cheapflights users on 4/22. 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.
mié. 7/25:35 amORD - GCM
1 stop5h 50mDelta
mar. 7/812:50 pmGCM - ORD
1 stop8h 31mDelta
Deal found 4/22$610
This Delta deal was found by Cheapflights users on 4/22. 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.
mié. 5/286:00 amMDW - GCM
1 stop5h 20mDelta
mar. 6/312:35 pmGCM - MDW
1 stop8h 52mDelta
Deal found 4/22$610
This American Airlines deal was found by Cheapflights users on 4/22. 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.
mié. 5/285:00 amORD - GCM
1 stop6h 10mAmerican Airlines
mar. 6/312:10 pmGCM - ORD
2 stops11h 46mAmerican Airlines
Deal found 4/22$614
This Kiwi.com deal was found by Cheapflights users on 4/22. 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.
dom. 6/154:06 pmMDW - GCM
1 stop25h 14mMultiple Airlines
dom. 6/2212:40 pmGCM - MDW
1 stop9h 52mMultiple Airlines
Deal found 4/22$681
This United Airlines deal was found by Cheapflights users on 4/22. 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.
sáb. 5/179:26 amORD - GCM
Nonstop4h 04mUnited Airlines
sáb. 5/241:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 4/22$690

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 abril 22, 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

dom. 6/1

8:25 pm-11:55 am

1 stop15h 30m

George Town Owen Roberts Intl

jue. 6/5

12:50 pm-7:59 am

1 stop19h 09m

$491

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 5/6

7:00 pm-4:10 pm

1 stop21h 10m

George Town Owen Roberts Intl

vie. 5/9

4:45 pm-8:07 pm

2 stops27h 22m

$492

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 5/17

6:35 am-2:50 pm

2 stops8h 15m

George Town Owen Roberts Intl

sáb. 5/24

3:50 pm-8:40 am

2 stops16h 50m

$566

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 7/2

5:35 am-11:25 am

1 stop5h 50m

George Town Owen Roberts Intl

mar. 7/8

12:50 pm-9:21 pm

1 stop8h 31m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 5/28

6:00 am-11:20 am

1 stop5h 20m

George Town Owen Roberts Intl

mar. 6/3

12:35 pm-9:27 pm

1 stop8h 52m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 5/28

5:00 am-11:10 am

1 stop6h 10m

George Town Owen Roberts Intl

mar. 6/3

12:10 pm-11:56 pm

2 stops11h 46m

$614

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 6/15

4:06 pm-5:20 pm

1 stop25h 14m

George Town Owen Roberts Intl

dom. 6/22

12:40 pm-10:32 pm

1 stop9h 52m

$681

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 5/17

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

sáb. 5/24

1:45 pm-6:07 pm

Nonstop4h 22m

$690

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 7/22

7:00 am-4:10 pm

1 stop9h 10m

$178

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 5/25

8:25 pm-11:55 am

1 stop15h 30m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 17 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 abril 22, 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 abril 22, 2025.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about Southwest, Delta and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,683 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Air Canada
7.0
Good
9,179 reviews
Southwest
8.0
Very good
4,287 reviews

Comfort

8.0

Food

7.1

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.6

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $197. 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 $574 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $465.

  • 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

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Alternative routes for Chicago to Cayman Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 abril 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$668FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$659FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$502Average$707FlexibilityNo cancel feeOn-time69%

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