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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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
nov. 9 — nov. 161
1 adult
sáb. 11/9
sáb. 11/16
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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 noviembre 4, 2024.

This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
mar. 12/38:02 pmORD - GCM
1 stop19h 08mMultiple Airlines
jue. 12/511:30 amGCM - ORD
2 stops13h 21mMultiple Airlines
Deal found 11/3$477
This Gotogate deal was found by Cheapflights users on 11/4. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 12/154:00 pmORD - GCM
1 stop20h 40mAir Canada
dom. 12/224:00 pmGCM - ORD
1 stop28h 32mAir Canada
Deal found 11/4$567
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/246:00 amMDW - GCM
1 stop5h 27mDelta
mar. 12/313:47 pmGCM - MDW
1 stop7h 19mDelta
Deal found 11/4$578
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/245:40 amORD - GCM
1 stop5h 47mDelta
mar. 12/313:47 pmGCM - ORD
1 stop9h 09mDelta
Deal found 11/4$578
This American Airlines deal was found by Cheapflights users on 11/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/315:02 amORD - GCM
2 stops8h 28mAmerican Airlines
mar. 1/71:00 pmGCM - ORD
2 stops10h 04mAmerican Airlines
Deal found 11/4$583
This Southwest deal was found by Cheapflights users on 11/4. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 12/246:00 amMDW - GCM
1 stop5h 55mSouthwest
dom. 12/291:50 pmGCM - MDW
2 stops11h 30mSouthwest
Deal found 11/4$619
This United Airlines deal was found by Cheapflights users on 11/3. 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. 12/78:39 amORD - GCM
Nonstop3h 56mUnited Airlines
sáb. 12/142:40 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 11/3$644
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
jue. 11/212:31 pmMDW - GCM
1 stop24h 14mMultiple Airlines
lun. 11/257:00 amGCM - MDW
1 stop10h 21mMultiple Airlines
Deal found 11/3$661
This FlightHub deal was found by Cheapflights users on 11/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 12/219:50 amORD - CYB
2 stops31h 00mMultiple Airlines
vie. 12/2710:55 amCYB - ORD
2 stops23h 02mMultiple Airlines
Deal found 11/4$1,216
This CheapOair deal was found by Cheapflights users on 11/3. 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.
mar. 12/37:17 pmMDW - GCM
2 stops41h 32mWestJet
dom. 12/82:50 pmGCM - MDW
2 stops23h 41mWestJet
Deal found 11/3$3,234

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 2,455,398 searches. Data last updated noviembre 4, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 12/4

8:02 pm-9:20 pm

1 stop24h 18m

$168

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 1/1

5:59 pm-3:00 pm

2 stops20h 01m

$241

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 1/3

6:55 pm-11:20 am

1 stop15h 25m

$252

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mié. 12/25

6:00 am-12:27 pm

1 stop5h 27m

$292

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 12/27

7:33 pm-6:58 pm

1 stop22h 25m

$321

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 1/5

8:48 am-1:45 pm

Nonstop3h 57m

$333

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 1/19

11:20 am-1:49 pm

2 stops25h 29m

$337

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

lun. 1/20

7:45 am-4:10 pm

1 stop7h 25m

$176

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 12/28

8:10 pm-12:55 pm

2 stops15h 45m

$451

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 1/20

5:45 am-12:44 pm

1 stop5h 59m

$292

Flights are sorted by cheapest first

Deals found on 11/3

Showing 1-10 of 24 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 noviembre 4, 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 noviembre 4, 2024.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about Southwest, United Airlines 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
5,089 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Reviews

1 / 10

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

Southwest
8.1
Very good
5,089 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Reviews

1 / 10

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

Delta
8.0
Very good
8,829 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Reviews

1 / 10

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

JetBlue
7.5
Good
3,493 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Reviews

1 / 10

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

United Airlines
7.4
Good
9,226 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

Reviews

1 / 10

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

WestJet
7.3
Good
2,803 reviews
Southwest
8.1
Very good
5,089 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Food

7.2

Boarding

8.3

Entertainment

7.7

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.

  • Can I find flights from Chicago to Cayman Islands for under $500 on Cheapflights?

    Yes, there are multiple flights from Chicago to Cayman Islands for under $500. The cheapest flight booked recently is on Multiple Airlines for just $477, but on average you can expect to pay $831.

  • Are there nonstop flights from Chicago to Cayman Islands for under $700 on Cheapflights?

    Cheapflights has at least 2 direct flights from Chicago to Cayman Islands under $700. A good price for a nonstop flight from Chicago to Cayman Islands is less than $629.

  • Are there last-minute flights available from Chicago to Cayman Islands for under $900?

    There are currently 3+ open flights from Chicago to Cayman Islands within the next 7 days for less than $900.

  • 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 $241. However, be on the lookout for offers from JetBlue 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 $577 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $307 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $471.

  • What does ORD to GCM mean?

    Great question - ORD to GCM just means Chicago O'Hare Intl Airport to George Town Owen Roberts Intl Airport. Now you’ll know what these unique codes when you look for flights! Cayman Brac Gerrard-Smith Airport (CYB), Little Cayman Airport (LYB) are other airports near this flight route and their unique identifiers/IATA codes.

  • Can I find deals for flights from Chicago to Cayman Islands that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Cayman Islands flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Cayman Islands with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Cayman Islands flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • 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.

  • Can I find deals for flights from Chicago to Cayman Islands that allow pets onboard?

    Many airlines flying from Chicago to Cayman Islands offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Cayman Islands?

    Yes, you can often find last-minute deals on Chicago to Cayman Islands flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Cayman Islands flight deals updated?

    The Chicago to Cayman Islands flight deals you see on this page were last updated on 11/4.

  • 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.

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 2,455,398 searches. Data last updated noviembre 4, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$550FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$368Average$597FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$405Average$650FlexibilityNo cancel feeOn-time69%
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