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Cheap flights from Chicago (CHI) to the Cayman Islands from $204

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 5/4. 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 21 — Apr 281
From?
To?
Sun 4/21
Sun 4/28
1 adult, Economy
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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 3,165,818 searches. Data last updated April 16, 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.
Wed 6/125:30 amORD - GCM
1 stop6h 09mAmerican Airlines
Tue 6/1812:40 pmGCM - ORD
1 stop6h 50mAmerican Airlines
Deal found 4/15$575
Sat 5/256:45 pmORD - GCM
1 stop16h 10mAmerican Airlines
Wed 5/292:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Deal found 4/15$577
Wed 6/125:30 amORD - GCM
1 stop6h 09mAmerican Airlines
Tue 6/1812:15 pmGCM - ORD
2 stops11h 43mAmerican Airlines
Deal found 4/15$580
Fri 9/65:30 amORD - GCM
1 stop7h 36mAmerican Airlines
Fri 9/131:20 pmGCM - ORD
2 stops10h 16mAmerican Airlines
Deal found 4/15$605
Mon 7/295:28 amORD - GCM
1 stop6h 06mAmerican Airlines
Sun 8/411:55 amGCM - ORD
1 stop21h 10mAmerican Airlines
Deal found 4/15$619
Thu 5/165:15 amORD - GCM
1 stop8h 15mAmerican Airlines
Mon 5/202:30 pmGCM - ORD
1 stop6h 59mAmerican Airlines
Deal found 4/15$625
Sat 6/85:07 amORD - GCM
2 stops8h 53mAmerican Airlines
Sat 6/155:35 pmGCM - ORD
1 stop15h 08mAmerican Airlines
Deal found 4/15$631
Fri 8/236:25 pmORD - GCM
1 stop16h 41mAmerican Airlines
Wed 8/282:53 pmGCM - ORD
1 stop8h 43mAmerican Airlines
Deal found 4/15$640
Fri 8/235:30 amORD - GCM
1 stop7h 36mAmerican Airlines
Wed 8/283:18 pmGCM - ORD
2 stops8h 18mAmerican Airlines
Deal found 4/15$645

Cheap United Airlines flights from Chicago to Cayman Islands

Explore cheap flight options specifically provided by United 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 3,165,818 searches. Data last updated April 16, 2024.
To aid your search, here are some of the cheapest United Airlines flights we've found from Chicago to Cayman Islands. Deals frequently update to provide users with more options.
Tue 6/118:45 pmORD - GCM
1 stop15h 50mUnited Airlines
Sun 6/162:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/16$593
Mon 5/138:48 amORD - GCM
1 stop6h 12mUnited Airlines
Mon 5/274:15 pmGCM - ORD
1 stop15h 25mUnited Airlines
Deal found 4/14$668
Sun 6/168:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/221:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/15$669
Sun 6/166:00 amORD - GCM
1 stop6h 35mUnited Airlines
Sat 6/221:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/15$673
Mon 7/299:15 pmORD - GCM
1 stop15h 20mUnited Airlines
Sun 8/42:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/15$683
Sat 5/259:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Wed 5/294:15 pmGCM - ORD
1 stop15h 25mUnited Airlines
Deal found 4/15$689
Fri 5/178:48 amORD - GCM
1 stop6h 12mUnited Airlines
Mon 5/274:15 pmGCM - ORD
1 stop15h 25mUnited Airlines
Deal found 4/14$693
Mon 7/112:45 pmORD - GCM
1 stop23h 50mUnited Airlines
Sun 7/72:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/14$702
Sat 6/89:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/151:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/15$704

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 3,165,818 searches. Prices were last updated on April 16, 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.
Wed 5/157:17 pmMDW - GCM
1 stop26h 03mMultiple Airlines
Wed 5/2211:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/15$419
Wed 5/159:15 pmORD - GCM
1 stop24h 05mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/15$438
Mon 4/296:55 amMDW - GCM
2 stops33h 15mMultiple Airlines
Wed 5/111:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/16$449
Wed 5/159:25 pmORD - GCM
2 stops23h 55mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/15$468
Sun 5/56:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Mon 5/64:45 pmGCM - ORD
1 stop15h 43mMultiple Airlines
Deal found 4/14$471
Tue 4/307:27 amORD - GCM
1 stop8h 43mMultiple Airlines
Wed 5/111:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/16$488
Wed 5/1510:58 amORD - GCM
3 stops34h 22mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/15$490
Thu 4/257:13 pmMDW - GCM
1 stop16h 27mMultiple Airlines
Wed 5/111:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/16$492
Thu 5/162:28 pmMDW - GCM
2 stops21h 12mMultiple Airlines
Thu 5/234:45 pmGCM - MDW
1 stop25h 42mMultiple Airlines
Deal found 4/16$493

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 3,165,818 searches. Data last updated April 16, 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.
Wed 5/157:17 pmMDW - GCM
1 stop26h 03mMultiple Airlines
Wed 5/2211:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/15$419
Wed 5/159:15 pmORD - GCM
1 stop24h 05mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/15$438
Mon 4/296:55 amMDW - GCM
2 stops33h 15mMultiple Airlines
Wed 5/111:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/16$449
Wed 5/159:25 pmORD - GCM
2 stops23h 55mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/15$468
Sun 5/56:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Mon 5/64:45 pmGCM - ORD
1 stop15h 43mMultiple Airlines
Deal found 4/14$471
Tue 4/307:27 amORD - GCM
1 stop8h 43mMultiple Airlines
Wed 5/111:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/16$488
Wed 5/1510:58 amORD - GCM
3 stops34h 22mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/15$490
Thu 4/257:13 pmMDW - GCM
1 stop16h 27mMultiple Airlines
Wed 5/111:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/16$492
Thu 5/162:28 pmMDW - GCM
2 stops21h 12mMultiple Airlines
Thu 5/234:45 pmGCM - MDW
1 stop25h 42mMultiple Airlines
Deal found 4/16$493

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 3,165,818 searches. Data last updated April 16, 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.
Sun 6/168:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/221:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/15$669
Sat 6/89:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/151:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/16$704
Sat 6/299:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/61:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/16$744
Sat 6/299:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/61:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/15$789
Sat 4/278:45 amORD - GCM
Nonstop3h 55mUnited Airlines
Sun 4/283:30 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/16$964
Sat 8/39:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 8/101:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/15$1,294

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 3,165,818 searches. Data last updated April 16, 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.
Thu 4/257:13 pmMDW - GCM
1 stop16h 27mMultiple Airlines
Wed 5/111:30 amGCM - MDW
1 stop6h 57mMultiple Airlines
Deal found 4/16$492
Tue 4/237:27 amORD - GCM
1 stop8h 43mMultiple Airlines
Wed 5/111:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/16$495
Mon 4/225:25 pmORD - GCM
1 stop22h 45mMultiple Airlines
Tue 4/3011:30 amGCM - ORD
1 stop20h 58mMultiple Airlines
Deal found 4/16$497
Mon 4/225:25 pmORD - GCM
1 stop22h 45mMultiple Airlines
Wed 5/111:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/16$498
Thu 4/257:13 pmMDW - GCM
1 stop16h 27mMultiple Airlines
Tue 4/3011:30 amGCM - MDW
1 stop6h 53mMultiple Airlines
Deal found 4/16$503
Tue 4/237:27 amORD - GCM
1 stop8h 43mMultiple Airlines
Mon 4/299:30 amGCM - ORD
1 stop22h 58mMultiple Airlines
Deal found 4/16$511
Mon 4/225:25 pmORD - GCM
1 stop22h 45mMultiple Airlines
Sun 4/282:00 pmGCM - ORD
1 stop19h 18mMultiple Airlines
Deal found 4/16$513
Wed 4/248:59 pmORD - GCM
1 stop24h 21mMultiple Airlines
Sun 4/282:00 pmGCM - ORD
1 stop19h 18mMultiple Airlines
Deal found 4/16$516
Thu 4/259:24 amORD - GCM
1 stop11h 56mMultiple Airlines
Wed 5/111:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/16$518

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 3,165,818 searches. Data last updated April 16, 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.
Sat 5/42:15 pmORD - GCM
1 stop24h 20mAir Canada
Deal found 4/14$204
Sun 6/29:53 pmMDW - GCM
2 stops42h 17mMultiple Airlines
Deal found 4/15$213
Sat 5/43:45 pmORD - GCM
2 stops22h 50mAir Canada
Deal found 4/14$229
Wed 6/196:15 pmORD - CYB
2 stops37h 50mMultiple Airlines
Deal found 4/14$238
Sun 6/26:21 pmMDW - GCM
1 stop24h 19mMultiple Airlines
Deal found 4/15$242
Sat 5/48:25 amORD - GCM
3 stops31h 45mMultiple Airlines
Deal found 4/14$266
Sun 6/210:03 amORD - GCM
1 stop8h 37mMultiple Airlines
Deal found 4/15$273
Sun 6/27:35 amORD - GCM
2 stops29h 25mMultiple Airlines
Deal found 4/15$275
Sun 6/210:57 pmORD - GCM
3 stops41h 13mMultiple Airlines
Deal found 4/15$306

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 3,165,818 searches. Data last updated April 16, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$419 - $603

Route

Depart

Return

Price

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Wed 5/15

1 stop26h 03m

George Town Owen Roberts Intl

Wed 5/22

1 stop6h 57m

$419

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/15

1 stop24h 05m

George Town Owen Roberts Intl

Wed 5/22

1 stop7h 07m

$438

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Mon 4/29

2 stops33h 15m

George Town Owen Roberts Intl

Wed 5/1

1 stop6h 57m

$449

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/15

2 stops23h 55m

George Town Owen Roberts Intl

Wed 5/22

1 stop7h 07m

$468

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 5/9

1 stop8h 35m

George Town Owen Roberts Intl

Sun 5/12

1 stop18h 09m

$527

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 5/9

1 stop8h 35m

George Town Owen Roberts Intl

Sun 5/12

2 stops18h 21m

$530

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 6/12

1 stop6h 09m

George Town Owen Roberts Intl

Tue 6/18

1 stop6h 50m

$575

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 6/11

1 stop15h 50m

George Town Owen Roberts Intl

Sun 6/16

Nonstop4h 10m

$593

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 5/13

1 stop14h 41m

George Town Owen Roberts Intl

Sun 5/26

1 stop11h 04m

$603

Flights are sorted by cheapest first

Deals found on 4/15

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 16, 2024.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about American Airlines, United Airlines and Delta. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.1
Very good
11,123 reviews
Check prices

Food

7.5

Overall

8.1

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

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!

Delta
8.1
Very good
11,123 reviews
Delta
8.1
Very good
11,123 reviews
Check prices

Food

7.5

Overall

8.1

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

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!

WestJet
7.5
Good
3,007 reviews
Delta
8.1
Very good
11,123 reviews
Check prices

Food

7.5

Overall

8.1

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

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!

United Airlines
7.4
Good
11,360 reviews
Delta
8.1
Very good
11,123 reviews
Check prices

Food

7.5

Overall

8.1

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

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!

American Airlines
7.3
Good
14,952 reviews
Delta
8.1
Very good
11,123 reviews
Check prices

Food

7.5

Overall

8.1

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

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!

Air Canada
7.0
Good
6,833 reviews
Delta
8.1
Very good
11,123 reviews
Check prices

Food

7.5

Overall

8.1

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

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 $419, but on average you can expect to pay $498.

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

    Cheapflights has at least 6 direct flights from Chicago to Cayman Islands under $700. A good price for a nonstop flight from Chicago to Cayman Islands is less than $860.

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

    There are currently 20+ 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 $204. However, be on the lookout for offers from United Airlines and WestJet, 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 most popular airlines that fly from Chicago to Cayman Islands?

    The most popular airlines flying from Chicago to Cayman Islands are American Airlines, Delta and Linear Air Taxi. Something to consider prior to booking your flight.

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

    On average you can expect to pay $483 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 $438.

  • 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 4/16.

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 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 3,165,818 searches. Data last updated April 16, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$353Average$546FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$372Average$581FlexibilityNo 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
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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.
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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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