Cheap flights from Chicago (CHI) to the Cayman Islands from $152

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 4/30. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — GCM
Apr 16 — Apr 231

How far in advance should I book a flight from Chicago to Cayman Islands?

Find a great deal and save up to 50% by booking at least 34 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Chicago to Cayman Islands within the next two weeks, with the cheapest ticket starting at $655.

What is the cheapest month to fly from Chicago to Cayman Islands?

January is one of the best times of the year to fly to Cayman Islands from Chicago. Prices for January average $629 per person but you can even find prices for as low as $230. The most expensive prices can be found in the month of December. Opting for a January flight can save you 41% on your journey compared to booking in December

When is the cheapest time to fly from Chicago to Cayman Islands (CHI - KY)?

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.

Cheap American Airlines flights from Chicago to Cayman Islands

Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Cayman Islands. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
Consider these cheap American Airlines flights we've found departing from Chicago to Cayman Islands. Make sure to double check the flight details before booking.
Sat 6/298:32 pmORD - GCM
1 stop15h 07mAmerican Airlines
Fri 7/512:35 pmGCM - ORD
1 stop11h 20mAmerican Airlines
Deal found 4/11$575
Sat 5/256:45 pmORD - GCM
1 stop16h 10mAmerican Airlines
Wed 5/292:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Deal found 4/10$577
Wed 8/145:30 amORD - GCM
2 stops7h 17mAmerican Airlines
Wed 8/211:20 pmGCM - ORD
2 stops8h 14mAmerican Airlines
Deal found 4/10$580
Sat 5/118:37 pmORD - GCM
2 stops14h 18mAmerican Airlines
Wed 5/1512:15 pmGCM - ORD
2 stops9h 14mAmerican Airlines
Deal found 4/9$581
Fri 9/65:30 amORD - GCM
1 stop7h 36mAmerican Airlines
Fri 9/132:53 pmGCM - ORD
1 stop6h 41mAmerican Airlines
Deal found 4/10$600
Fri 9/65:30 amORD - GCM
1 stop7h 36mAmerican Airlines
Fri 9/131:20 pmGCM - ORD
2 stops10h 16mAmerican Airlines
Deal found 4/10$605
Sat 5/188:37 pmORD - GCM
2 stops14h 18mAmerican Airlines
Sat 5/252:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Deal found 4/10$606
Thu 5/167:30 amORD - GCM
1 stop6h 00mAmerican Airlines
Mon 5/202:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Deal found 4/10$625
Thu 5/167:30 amORD - GCM
1 stop6h 00mAmerican Airlines
Mon 5/2012:15 pmGCM - ORD
2 stops9h 39mAmerican Airlines
Deal found 4/10$671

Cheap Delta flights from Chicago to Cayman Islands

Explore cheap flight options specifically provided by Delta for the route between Chicago and Cayman Islands. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
To aid your search, here are some of the cheapest Delta flights we've found from Chicago to Cayman Islands. Deals frequently update to provide users with more options.
Wed 8/147:55 pmORD - GCM
1 stop15h 35mDelta
Fri 8/2312:50 pmGCM - ORD
1 stop11h 09mDelta
Deal found 4/10$578
Wed 8/145:55 pmORD - GCM
2 stops17h 35mDelta
Fri 8/2312:50 pmGCM - ORD
1 stop8h 21mDelta
Deal found 4/10$583
Sat 8/176:00 amORD - GCM
1 stop5h 30mDelta
Thu 8/2212:50 pmGCM - ORD
1 stop11h 09mDelta
Deal found 4/10$603
Sat 8/176:00 amORD - GCM
1 stop5h 30mDelta
Thu 8/2212:50 pmGCM - ORD
2 stops18h 32mDelta
Deal found 4/10$608
Tue 10/85:59 pmMDW - GCM
2 stops41h 31mDelta
Sun 10/1312:50 pmGCM - MDW
1 stop8h 54mDelta
Deal found 4/9$618
Fri 9/66:00 amMDW - GCM
1 stop5h 30mDelta
Fri 9/1312:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 4/10$620
Thu 8/156:00 amORD - GCM
1 stop5h 30mDelta
Sat 8/2412:50 pmGCM - ORD
1 stop6h 58mDelta
Deal found 4/10$628
Thu 6/206:00 amORD - GCM
1 stop5h 40mDelta
Mon 6/241:05 pmGCM - ORD
2 stops18h 27mDelta
Deal found 4/10$633
Sat 9/76:00 amMDW - GCM
1 stop5h 30mDelta
Sun 9/1512:50 pmGCM - MDW
2 stops19h 55mDelta
Deal found 4/10$643

Cheap Chicago to Cayman Islands flights in April & May 2024

Find cheap flight options from Chicago to Cayman Islands specifically for the months of April and May 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,194,136 searches. Prices were last updated on April 11, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in April and May 2024. More deals are always being added, so be sure to check back regularly.
Sat 5/119:35 pmORD - GCM
1 stop21h 05mMultiple Airlines
Wed 5/1511:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/9$429
Wed 5/297:23 pmMDW - GCM
1 stop25h 57mMultiple Airlines
Tue 6/411:30 amGCM - MDW
1 stop20h 02mMultiple Airlines
Deal found 4/10$435
Wed 5/17:50 pmORD - GCM
1 stop25h 30mMultiple Airlines
Mon 5/64:45 pmGCM - ORD
1 stop15h 43mMultiple Airlines
Deal found 4/9$438
Fri 4/199:20 pmORD - GCM
1 stop20h 30mMultiple Airlines
Mon 4/229:30 amGCM - ORD
2 stops25h 17mMultiple Airlines
Deal found 4/10$439
Wed 5/295:19 pmORD - GCM
1 stop19h 41mMultiple Airlines
Tue 6/411:30 amGCM - ORD
1 stop20h 59mMultiple Airlines
Deal found 4/10$442
Sat 5/113:54 pmMDW - GCM
1 stop26h 46mMultiple Airlines
Wed 5/1511:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/9$445
Fri 4/199:20 pmORD - GCM
1 stop20h 30mMultiple Airlines
Mon 4/229:30 amGCM - ORD
1 stop22h 58mMultiple Airlines
Deal found 4/10$448
Wed 5/18:59 pmORD - GCM
1 stop24h 21mMultiple Airlines
Mon 5/64:45 pmGCM - ORD
2 stops18h 02mMultiple Airlines
Deal found 4/9$454
Tue 5/289:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Sun 6/25:10 pmGCM - ORD
1 stop28h 36mMultiple Airlines
Deal found 4/10$457

Chicago to Cayman Islands 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Cayman Islands in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in April and May 2024. More deals are always being added, so be sure to check back regularly.
Sat 5/119:35 pmORD - GCM
1 stop21h 05mMultiple Airlines
Wed 5/1511:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/9$429
Wed 5/297:23 pmMDW - GCM
1 stop25h 57mMultiple Airlines
Tue 6/411:30 amGCM - MDW
1 stop20h 02mMultiple Airlines
Deal found 4/10$435
Wed 5/17:50 pmORD - GCM
1 stop25h 30mMultiple Airlines
Mon 5/64:45 pmGCM - ORD
1 stop15h 43mMultiple Airlines
Deal found 4/9$438
Fri 4/199:20 pmORD - GCM
1 stop20h 30mMultiple Airlines
Mon 4/229:30 amGCM - ORD
2 stops25h 17mMultiple Airlines
Deal found 4/10$439
Wed 5/295:19 pmORD - GCM
1 stop19h 41mMultiple Airlines
Tue 6/411:30 amGCM - ORD
1 stop20h 59mMultiple Airlines
Deal found 4/10$442
Sat 5/113:54 pmMDW - GCM
1 stop26h 46mMultiple Airlines
Wed 5/1511:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/9$445
Tue 6/49:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Tue 6/1811:30 amGCM - ORD
1 stop20h 59mMultiple Airlines
Deal found 4/9$447
Fri 4/199:20 pmORD - GCM
1 stop20h 30mMultiple Airlines
Mon 4/229:30 amGCM - ORD
1 stop22h 58mMultiple Airlines
Deal found 4/10$448
Wed 5/18:59 pmORD - GCM
1 stop24h 21mMultiple Airlines
Mon 5/64:45 pmGCM - ORD
2 stops18h 02mMultiple Airlines
Deal found 4/9$454

Non-stop flights to Cayman Islands from Chicago

Discover non-stop flight options from Chicago to Cayman Islands. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
For a quicker trip, book one of these direct flights from Chicago to Cayman Islands. Search for alternative flights from Chicago to Cayman Islands by utilizing the search form above.
Sat 6/19:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/81:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/10$614
Sat 6/19:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/81:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/10$635
Sat 6/89:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/151:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/11$704
Sat 6/299:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/61:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/11$744
Sat 7/69:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/131:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/10$1,034

Chicago to Cayman Islands flights leaving soon

Find last-minute flight options from Chicago to Cayman Islands for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
Book one of these great deals on flights from Chicago to Cayman Islands. It's wise to confirm all flight details are correct before booking.
Fri 4/199:20 pmORD - GCM
1 stop20h 30mMultiple Airlines
Mon 4/229:30 amGCM - ORD
2 stops25h 17mMultiple Airlines
Deal found 4/10$439
Fri 4/199:20 pmORD - GCM
1 stop20h 30mMultiple Airlines
Mon 4/229:30 amGCM - ORD
1 stop22h 58mMultiple Airlines
Deal found 4/10$448
Wed 4/174:56 pmMDW - GCM
2 stops28h 24mMultiple Airlines
Wed 4/2411:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/11$481
Wed 4/1710:00 pmORD - GCM
2 stops23h 20mMultiple Airlines
Wed 4/2411:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/11$529
Wed 4/177:50 pmORD - GCM
1 stop25h 30mMultiple Airlines
Wed 4/2411:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/11$606
Fri 4/197:03 amORD - GCM
3 stops34h 47mMultiple Airlines
Mon 4/229:30 amGCM - ORD
3 stops35h 15mMultiple Airlines
Deal found 4/10$620
Fri 4/196:21 pmORD - GCM
2 stops23h 29mMultiple Airlines
Mon 4/229:30 amGCM - ORD
3 stops35h 15mMultiple Airlines
Deal found 4/10$638
Fri 4/197:03 amORD - GCM
3 stops34h 47mMultiple Airlines
Mon 4/229:30 amGCM - ORD
1 stop7h 03mMultiple Airlines
Deal found 4/10$648
Wed 4/179:25 pmORD - GCM
3 stops18h 15mMultiple Airlines
Wed 4/244:00 pmGCM - ORD
1 stop14h 03mMultiple Airlines
Deal found 4/11$816

One-way flights to Cayman Islands from Chicago

Search for one-way flight options from Chicago to Cayman Islands. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,194,136 searches. Data last updated April 11, 2024.
Users in need of a one-way flight from Chicago to Cayman Islands can choose from these deals. Users can also find round-trip Chicago to Cayman Islands flights by using the search form above.
Tue 4/307:27 amORD - GCM
1 stop8h 43mMultiple Airlines
Deal found 4/10$152
Tue 4/307:03 amORD - GCM
2 stops33h 07mMultiple Airlines
Deal found 4/10$177
Sat 5/184:00 pmORD - GCM
1 stop22h 35mAir Canada
Deal found 4/10$200
Tue 4/3011:47 amORD - GCM
3 stops28h 23mMultiple Airlines
Deal found 4/10$206
Wed 4/1710:12 amMDW - GCM
2 stops35h 08mMultiple Airlines
Deal found 4/11$209
Sun 5/1910:49 pmMDW - GCM
2 stops41h 21mMultiple Airlines
Deal found 4/10$219
Wed 4/1710:00 pmORD - GCM
2 stops37h 40mMultiple Airlines
Deal found 4/11$221
Sat 5/185:45 pmMDW - GCM
1 stop22h 25mMultiple Airlines
Deal found 4/10$223
Sun 5/196:00 amORD - GCM
1 stop8h 35mAir Canada
Deal found 4/10$225

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 3,194,136 searches. Data last updated April 11, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$429 - $593

Route

Depart

Return

Price

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 5/11

1 stop21h 05m

George Town Owen Roberts Intl

Wed 5/15

1 stop7h 07m

$429

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Wed 5/29

1 stop25h 57m

George Town Owen Roberts Intl

Tue 6/4

1 stop20h 02m

$435

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/1

1 stop25h 30m

George Town Owen Roberts Intl

Mon 5/6

1 stop15h 43m

$438

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/29

1 stop19h 41m

George Town Owen Roberts Intl

Tue 6/4

1 stop20h 59m

$442

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/29

1 stop22h 35m

George Town Owen Roberts Intl

Sun 6/2

2 stops18h 16m

$495

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 9/7

2 stops19h 55m

George Town Owen Roberts Intl

Sun 9/15

1 stop8h 03m

$505

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 6/29

1 stop15h 07m

George Town Owen Roberts Intl

Fri 7/5

1 stop11h 20m

$575

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 8/14

1 stop15h 35m

George Town Owen Roberts Intl

Fri 8/23

1 stop11h 09m

$578

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/28

1 stop15h 04m

George Town Owen Roberts Intl

Sun 6/2

Nonstop4h 10m

$593

Flights are sorted by cheapest first

Deals found on 4/9

No data available for this route at this time. Please check back soon.

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 April 11, 2024.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about American Airlines, 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.
8.1
Very good
11,206 reviews

Boarding

8.2

Food

7.5

Comfort

7.9

Entertainment

8.0

Overall

8.1

Crew

8.6

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

8.1
Very good
11,206 reviews
8.1
Very good
11,206 reviews

Boarding

8.2

Food

7.5

Comfort

7.9

Entertainment

8.0

Overall

8.1

Crew

8.6

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

7.5
Good
3,007 reviews
8.1
Very good
11,206 reviews

Boarding

8.2

Food

7.5

Comfort

7.9

Entertainment

8.0

Overall

8.1

Crew

8.6

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

7.4
Good
11,391 reviews
8.1
Very good
11,206 reviews

Boarding

8.2

Food

7.5

Comfort

7.9

Entertainment

8.0

Overall

8.1

Crew

8.6

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

7.3
Good
15,011 reviews
8.1
Very good
11,206 reviews

Boarding

8.2

Food

7.5

Comfort

7.9

Entertainment

8.0

Overall

8.1

Crew

8.6

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

7.0
Good
6,809 reviews
8.1
Very good
11,206 reviews

Boarding

8.2

Food

7.5

Comfort

7.9

Entertainment

8.0

Overall

8.1

Crew

8.6

Reviews

1 / 10

I love the seamless way that delta ensures that my luggage is on board the plane, I get a notification that it's on board. I love boarding process, orderly and on time. Lots of room in Comfort plus and getting upgraded to first class was everything!

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 $429, but on average you can expect to pay $466.

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

    Cheapflights has at least 5 direct flights from Chicago to Cayman Islands under $700. A good price for a nonstop flight from Chicago to Cayman Islands is less than $746.

  • Are there last-minute flights available from Chicago to Cayman Islands for under $500?

    There are currently 12+ open flights from Chicago to Cayman Islands within the next 7 days for less than $500.

  • 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 $200. However, be on the lookout for offers from Delta and United Airlines, 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?

  • What are the most popular airlines that fly from Chicago to Cayman Islands?

  • What are the cheapest flights from Chicago to Cayman Islands?

    On average you can expect to pay $523 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $297 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $439.

  • 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 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 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 see available direct flights.

  • 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 do 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 4/10.

See more FAQs

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Top 4 airlines flying from Chicago to Cayman Islands

Discover the top 4 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 3,194,136 searches. Data last updated April 11, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$354Average$546FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$372Average$584FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
United AirlinesCheapest$401Average$644FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Linear Air TaxiCheapest$18,288Average$51,983FlexibilityNo cancel feeOn-timeN/A
Search Linear Air Taxi flights

Search flights from Chicago to Cayman Islands by cabin class

Find flights from Chicago to Cayman Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Chicago to Cayman Islands?

Cheapflights makes it easy to find Chicago to Cayman Islands flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Cayman Islands?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Cayman Islands from Chicago.

Can Cheapflights find flights from Chicago to Cayman Islands with no change fees?

Certainly. Search results for flights to Cayman Islands from Chicago shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Chicago to Cayman Islands become cheaper?

Yes, Cheapflights offers price alerts on Chicago to Cayman Islands flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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