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Cayman Islands

$180+ 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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Nov 26 — Dec 31
Tue 11/26
Tue 12/3
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 November 21, 2024.

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 November 21, 2024.

This Mytrip deal was found by Cheapflights users on 11/20. 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 12/116:37 pmORD - GCM
1 stop17h 23mMultiple Airlines
Sun 12/154:00 pmGCM - ORD
1 stop17h 57mMultiple Airlines
Deal found 11/20$562
This Southwest deal was found by Cheapflights users on 11/19. 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.
Mon 12/96:00 amMDW - GCM
1 stop5h 55mSouthwest
Thu 12/121:50 pmGCM - MDW
2 stops9h 30mSouthwest
Deal found 11/19$575
This United Airlines deal was found by Cheapflights users on 11/19. 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.
Wed 12/187:35 amORD - GCM
1 stop7h 50mUnited Airlines
Wed 12/252:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 11/19$608
This Priceline deal was found by Cheapflights users on 11/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/57:19 amORD - GCM
1 stop29h 21mAir Canada
Sun 12/84:00 pmGCM - ORD
1 stop28h 32mAir Canada
Deal found 11/20$617
This Delta deal was found by Cheapflights users on 11/21. 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 12/246:00 amMDW - GCM
1 stop7h 32mDelta
Tue 12/313:47 pmGCM - MDW
1 stop7h 19mDelta
Deal found 11/21$618
This American Airlines deal was found by Cheapflights users on 11/21. 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.
Tue 12/316:55 pmORD - GCM
1 stop16h 05mAmerican Airlines
Tue 1/71:40 pmGCM - ORD
1 stop6h 46mAmerican Airlines
Deal found 11/21$618
This Delta deal was found by Cheapflights users on 11/20. 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.
Thu 12/195:40 amORD - GCM
1 stop7h 52mDelta
Thu 12/261:52 pmGCM - ORD
1 stop8h 28mDelta
Deal found 11/20$643
This Kiwi.com deal was found by Cheapflights users on 11/20. 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 12/196:00 amMDW - GCM
1 stop14h 20mMultiple Airlines
Thu 12/264:45 pmGCM - MDW
2 stops21h 39mMultiple Airlines
Deal found 11/20$669
This CheapOair deal was found by Cheapflights users on 11/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/228:25 pmORD - CYB
2 stops20h 25mMultiple Airlines
Sat 12/283:40 pmCYB - ORD
2 stops42h 17mMultiple Airlines
Deal found 11/21$1,086
This CheapOair deal was found by Cheapflights users on 11/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/112:15 pmMDW - GCM
2 stops22h 34mWestJet
Sun 12/152:50 pmGCM - MDW
2 stops23h 41mWestJet
Deal found 11/20$3,094

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 2,612,795 searches. Data last updated November 21, 2024.

Fly from

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Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 2/19

7:25 am-4:10 pm

1 stop7h 45m

George Town Owen Roberts Intl

Fri 2/28

4:45 pm-8:44 am

1 stop16h 59m

$488

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 1/10

1:34 pm-9:20 pm

1 stop6h 46m

George Town Owen Roberts Intl

Fri 1/17

4:45 pm-12:29 pm

1 stop20h 44m

$505

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 2/25

5:45 am-12:55 pm

1 stop6h 10m

George Town Owen Roberts Intl

Sat 3/1

2:10 pm-11:15 pm

2 stops10h 05m

$532

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 3/18

8:48 am-12:45 pm

Nonstop3h 57m

George Town Owen Roberts Intl

Tue 3/25

1:50 pm-6:06 pm

Nonstop4h 16m

$574

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 2/23

6:00 am-12:44 pm

1 stop5h 44m

George Town Owen Roberts Intl

Fri 2/28

2:09 pm-10:20 pm

1 stop9h 11m

$588

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/1

6:30 pm-12:35 pm

1 stop17h 05m

George Town Owen Roberts Intl

Wed 2/5

3:15 pm-9:53 pm

1 stop7h 38m

$588

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 2/22

7:05 am-2:04 pm

1 stop5h 59m

George Town Owen Roberts Intl

Wed 2/26

2:09 pm-11:59 pm

1 stop10h 50m

$613

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 12/5

7:19 am-1:40 pm

1 stop29h 21m

George Town Owen Roberts Intl

Sun 12/8

4:00 pm-7:32 pm

1 stop28h 32m

$617

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Sun 12/22

8:25 pm-5:50 pm

2 stops20h 25m

Cayman Brac Gerrard-Smith

Sat 12/28

3:40 pm-8:57 am

2 stops42h 17m

$1,086

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 1/5

11:48 am-1:49 pm

2 stops25h 01m

George Town Owen Roberts Intl

Sun 1/12

2:50 pm-5:47 pm

2 stops27h 57m

$1,630

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/20

Showing 1-10 of 20 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 June is currently the most expensive (average of $560). 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 November 21, 2024.

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 November 21, 2024.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about Delta, American Airlines 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
5,005 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very good
5,005 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very good
8,755 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,172 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

WestJet
7.3
Good
2,811 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
5,005 reviews

Entertainment

7.7

Crew

8.7

Food

7.2

Boarding

8.2

Overall

8.1

Comfort

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 $240. However, be on the lookout for offers from Sun Country Air 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 $570 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $296 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $462.

  • 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 June is currently the most expensive (average of $560). 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 2,612,795 searches. Data last updated November 21, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$348Average$476FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$368Average$606FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$420Average$671FlexibilityNo cancel feeOn-time69%
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