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Cayman Islands

$151+ 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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Feb 28 — Mar 71
Fri 2/28
Fri 3/7
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 February 23, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$606
(Southwest)

One-way from

$151
(Mytrip)

Popular in

March

Cheapest in

September

Average price

$660

Good round-trip deal

$654 or less

Good one-way deal

$293 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 ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 23, 2025.

This Southwest deal was found by Cheapflights users on 2/22. 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.
Sat 5/37:55 pmMDW - GCM
2 stops15h 55mSouthwest
Sat 5/101:10 pmGCM - MDW
1 stop7h 15mSouthwest
Deal found 2/22$606
This Mytrip deal was found by Cheapflights users on 2/22. 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.
Wed 4/95:10 amORD - GCM
2 stops31h 33mMultiple Airlines
Sat 4/127:05 pmGCM - ORD
3 stops35h 28mMultiple Airlines
Deal found 2/22$608
This American Airlines deal was found by Cheapflights users on 2/23. 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.
Wed 4/97:00 amORD - GCM
1 stop5h 59mAmerican Airlines
Wed 4/1612:35 pmGCM - ORD
1 stop10h 04mAmerican Airlines
Deal found 2/23$609
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Thu 3/275:01 amMDW - GCM
1 stop13h 39mMultiple Airlines
Mon 3/312:00 pmGCM - MDW
1 stop7h 04mMultiple Airlines
Deal found 2/22$642
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Sat 4/129:26 amORD - GCM
Nonstop4h 04mUnited Airlines
Sat 4/191:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 2/22$645
This Air Canada deal was found by Cheapflights users on 2/23. 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.
Thu 3/206:13 pmORD - GCM
2 stops19h 47mAir Canada
Thu 3/273:00 pmGCM - ORD
1 stop18h 01mAir Canada
Deal found 2/23$660
This Delta deal was found by Cheapflights users on 2/22. 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.
Sat 4/126:00 amMDW - GCM
1 stop7h 20mDelta
Sat 4/1912:47 pmGCM - MDW
1 stop9h 35mDelta
Deal found 2/22$660
This Delta deal was found by Cheapflights users on 2/22. 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.
Tue 3/255:45 amORD - GCM
1 stop5h 53mDelta
Tue 4/11:03 pmGCM - ORD
1 stop10h 53mDelta
Deal found 2/22$695
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Sat 5/247:00 amORD - CYB
1 stop6h 20mMultiple Airlines
Mon 6/210:55 amCYB - ORD
2 stops20h 45mMultiple Airlines
Deal found 2/22$714
This WestJet deal was found by Cheapflights users on 2/22. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2111:48 amMDW - GCM
2 stops25h 01mWestJet
Mon 12/292:50 pmGCM - MDW
2 stops27h 54mWestJet
Deal found 2/22$3,499

Find flights from Chicago to Cayman Islands within your budget

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 February 23, 2025.

Fly from

Chicago

Fly to

Cayman Islands

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 5/3

7:55 pm-11:50 am

2 stops15h 55m

George Town Owen Roberts Intl

Sat 5/10

1:10 pm-8:25 pm

1 stop7h 15m

$606

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/9

5:10 am-12:43 pm

2 stops31h 33m

George Town Owen Roberts Intl

Sat 4/12

7:05 pm-6:33 am

3 stops35h 28m

$608

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 4/9

7:00 am-12:59 pm

1 stop5h 59m

George Town Owen Roberts Intl

Wed 4/16

12:35 pm-10:39 pm

1 stop10h 04m

$609

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 3/27

5:01 am-6:40 pm

1 stop13h 39m

George Town Owen Roberts Intl

Mon 3/31

2:00 pm-9:04 pm

1 stop7h 04m

$642

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 4/12

9:26 am-1:30 pm

Nonstop4h 04m

George Town Owen Roberts Intl

Sat 4/19

1:45 pm-6:07 pm

Nonstop4h 22m

$645

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 3/20

6:13 pm-2:00 pm

2 stops19h 47m

George Town Owen Roberts Intl

Thu 3/27

3:00 pm-9:01 am

1 stop18h 01m

$660

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 4/12

6:00 am-1:20 pm

1 stop7h 20m

George Town Owen Roberts Intl

Sat 4/19

12:47 pm-10:22 pm

1 stop9h 35m

$660

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/25

5:45 am-11:38 am

1 stop5h 53m

George Town Owen Roberts Intl

Tue 4/1

1:03 pm-11:56 pm

1 stop10h 53m

$695

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Sat 5/24

7:00 am-1:20 pm

1 stop6h 20m

Cayman Brac Gerrard-Smith

Mon 6/2

10:55 am-7:40 am

2 stops20h 45m

$714

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 4/11

7:05 pm-6:04 pm

1 stop22h 59m

$151

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

Showing 1-10 of 21 results
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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.

Travel insights for flights from Chicago to Cayman Islands

Get recent, data-driven insights about flights from Chicago to Cayman Islands including ideal travel times, pricing trends, and more.

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 February 23, 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 February 23, 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
8.1
Very good
4,385 reviews

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,385 reviews
Southwest
8.1
Very good
4,385 reviews

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,385 reviews

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,385 reviews

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,385 reviews

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,796 reviews
Southwest
8.1
Very good
4,385 reviews

Crew

8.7

Food

7.1

Boarding

8.2

Comfort

8.1

Entertainment

7.6

Overall

8.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 Sun Country Air, with whom users have recently found tickets for as low as $151. However, be on the lookout for offers from Air Canada and Southwest, 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 $578 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 $436.

  • 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.

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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 February 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$424Average$583FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$662FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$514Average$703FlexibilityNo cancel feeOn-time69%
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