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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 2/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jan 11 — Jan 181
Sat 1/11
Sat 1/18
1 adult, Economy
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Cheap flight deals from Chicago to Cayman Islands

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Cayman Islands (KY0). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 6, 2025.

Round-trip from

$576
(Southwest)

One-way from

$168
(Kiwi.com)
From Chicago (CHI) to Cayman Islands
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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 January 6, 2025.

This Southwest deal was found by Cheapflights users on 1/5. 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.
Fri 2/288:35 pmMDW - GCM
2 stops15h 45mSouthwest
Tue 3/41:50 pmGCM - MDW
2 stops20h 30mSouthwest
Deal found 1/5$576
This Kiwi.com deal was found by Cheapflights users on 1/4. 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 4/178:10 amORD - GCM
1 stop10h 35mMultiple Airlines
Sun 4/272:00 pmGCM - ORD
2 stops31h 06mMultiple Airlines
Deal found 1/4$576
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Fri 1/245:30 amMDW - GCM
1 stop9h 15mMultiple Airlines
Mon 1/277:00 amGCM - MDW
2 stops34h 16mMultiple Airlines
Deal found 1/6$583
This United Airlines deal was found by Cheapflights users on 1/5. 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.
Mon 3/178:48 amORD - GCM
Nonstop3h 57mUnited Airlines
Fri 3/211:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 1/5$589
This Delta deal was found by Cheapflights users on 1/6. 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 3/256:00 amMDW - GCM
1 stop5h 25mDelta
Tue 4/112:50 pmGCM - MDW
1 stop9h 37mDelta
Deal found 1/6$600
This Air Canada deal was found by Cheapflights users on 1/6. 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.
Sun 6/13:40 pmORD - GCM
2 stops20h 15mAir Canada
Thu 6/512:45 pmGCM - ORD
2 stops21h 07mAir Canada
Deal found 1/6$600
This American Airlines deal was found by Cheapflights users on 1/6. 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 2/265:00 amORD - GCM
1 stop6h 00mAmerican Airlines
Wed 3/51:00 pmGCM - ORD
2 stops9h 40mAmerican Airlines
Deal found 1/6$604
This Southwest deal was found by Cheapflights users on 1/6. 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.
Fri 3/74:20 pmORD - GCM
2 stops17h 55mSouthwest
Sat 3/151:10 pmGCM - ORD
2 stops20h 15mSouthwest
Deal found 1/6$606
This Delta deal was found by Cheapflights users on 1/5. 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 2/15:45 amORD - GCM
1 stop7h 19mDelta
Wed 2/52:04 pmGCM - ORD
1 stop7h 42mDelta
Deal found 1/5$635
This Kiwi.com deal was found by Cheapflights users on 1/6. 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.
Fri 1/312:02 pmORD - CYB
1 stop22h 18mMultiple Airlines
Thu 2/66:20 pmCYB - ORD
2 stops24h 00mMultiple Airlines
Deal found 1/6$646
This Flysmarter deal was found by Cheapflights users on 1/5. 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/108:48 amORD - GCM
Nonstop3h 57mLufthansa
Thu 3/131:50 pmGCM - ORD
Nonstop4h 16mLufthansa
Deal found 1/5$676
This Mytrip deal was found by Cheapflights users on 1/5. 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.
Sun 2/21:26 pmMDW - GCM
2 stops23h 17mWestJet
Sun 2/92:50 pmGCM - MDW
2 stops27h 53mWestJet
Deal found 1/5$861

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 January 6, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 2/28

8:35 pm-1:20 pm

2 stops15h 45m

George Town Owen Roberts Intl

Tue 3/4

1:50 pm-9:20 am

2 stops20h 30m

$576

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 4/17

8:10 am-6:45 pm

1 stop10h 35m

George Town Owen Roberts Intl

Sun 4/27

2:00 pm-9:06 pm

2 stops31h 06m

$576

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 1/24

5:30 am-3:45 pm

1 stop9h 15m

George Town Owen Roberts Intl

Mon 1/27

7:00 am-4:16 pm

2 stops34h 16m

$583

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 3/17

8:48 am-12:45 pm

Nonstop3h 57m

George Town Owen Roberts Intl

Fri 3/21

1:50 pm-6:06 pm

Nonstop4h 16m

$589

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 3/25

6:00 am-11:25 am

1 stop5h 25m

George Town Owen Roberts Intl

Tue 4/1

12:50 pm-10:27 pm

1 stop9h 37m

$600

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

3:40 pm-11:55 am

2 stops20h 15m

George Town Owen Roberts Intl

Thu 6/5

12:45 pm-9:52 am

2 stops21h 07m

$600

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/26

5:00 am-12:00 pm

1 stop6h 00m

George Town Owen Roberts Intl

Wed 3/5

1:00 pm-9:40 pm

2 stops9h 40m

$604

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 3/7

4:20 pm-11:15 am

2 stops17h 55m

George Town Owen Roberts Intl

Sat 3/15

1:10 pm-9:25 am

2 stops20h 15m

$606

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/1

5:45 am-2:04 pm

1 stop7h 19m

George Town Owen Roberts Intl

Wed 2/5

2:04 pm-8:46 pm

1 stop7h 42m

$635

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Fri 1/31

2:02 pm-1:20 pm

1 stop22h 18m

Cayman Brac Gerrard-Smith

Thu 2/6

6:20 pm-5:20 pm

2 stops24h 00m

$646

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 23 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 January 6, 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 January 6, 2025.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about Southwest, Delta and American 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
4,663 reviews

Boarding

8.2

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,663 reviews
Southwest
8.1
Very good
4,663 reviews

Boarding

8.2

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,513 reviews
Southwest
8.1
Very good
4,663 reviews

Boarding

8.2

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,940 reviews
Southwest
8.1
Very good
4,663 reviews

Boarding

8.2

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,663 reviews

Boarding

8.2

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,816 reviews
Southwest
8.1
Very good
4,663 reviews

Boarding

8.2

Food

7.2

Entertainment

7.7

Crew

8.7

Overall

8.1

Comfort

8.1

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 $216. 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 $589 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $312 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $484.

  • 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 January 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$501FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$371Average$618FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$445Average$687FlexibilityNo cancel feeOn-time69%
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