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Cheap flights from Chicago (CHI) to the Cayman Islands from $163

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 6/5. 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
May 1 — May 81
From?
To?
Wed 5/1
Wed 5/8
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 Air Canada flights from Chicago to Cayman Islands

Explore cheap flight options specifically provided by Air Canada 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 3,068,701 searches. Data last updated April 26, 2024.
Consider these cheap Air Canada flights we've found departing from Chicago to Cayman Islands. Make sure to double check the flight details before booking.
Wed 5/1511:00 amORD - GCM
1 stop27h 35mAir Canada
Thu 5/233:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 4/24$535
Thu 7/256:00 amORD - GCM
1 stop8h 35mAir Canada
Thu 8/83:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 4/24$552
Thu 6/276:00 amORD - GCM
1 stop8h 35mAir Canada
Thu 7/43:45 pmGCM - ORD
1 stop18h 09mAir Canada
Deal found 4/24$555
Wed 7/246:34 pmORD - GCM
2 stops20h 01mAir Canada
Sun 7/283:45 pmGCM - ORD
2 stops18h 16mAir Canada
Deal found 4/24$556
Sun 6/306:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 7/73:45 pmGCM - ORD
1 stop28h 59mAir Canada
Deal found 4/25$574
Sun 7/286:00 amORD - GCM
1 stop8h 35mAir Canada
Sun 8/43:45 pmGCM - ORD
2 stops16h 13mAir Canada
Deal found 4/25$639
Sat 6/294:00 pmORD - GCM
1 stop22h 35mAir Canada
Sun 7/73:45 pmGCM - ORD
2 stops18h 16mAir Canada
Deal found 4/25$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 3,068,701 searches. Data last updated April 26, 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.
Mon 6/247:50 pmORD - GCM
1 stop16h 45mUnited Airlines
Sun 6/302:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/24$593
Sun 7/288:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sun 8/41:40 pmGCM - ORD
1 stop7h 18mUnited Airlines
Deal found 4/25$599
Sun 5/268:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Tue 6/41:40 pmGCM - ORD
1 stop9h 19mUnited Airlines
Deal found 4/24$664
Mon 7/19:15 pmORD - GCM
1 stop15h 20mUnited Airlines
Mon 7/84:15 pmGCM - ORD
1 stop15h 25mUnited Airlines
Deal found 4/24$668
Sun 7/218:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/271:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/25$669
Sun 7/216:00 amORD - GCM
1 stop6h 35mUnited Airlines
Sat 7/271:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/25$673
Sun 6/308:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sun 7/72:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/24$679
Mon 7/16:00 amORD - GCM
1 stop6h 35mUnited Airlines
Sun 7/72:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/24$683
Sat 6/299:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Fri 7/54:15 pmGCM - ORD
1 stop15h 25mUnited Airlines
Deal found 4/24$689

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 3,068,701 searches. Prices were last updated on April 26, 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.
Tue 5/149:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
1 stop21h 15mMultiple Airlines
Deal found 4/24$406
Tue 5/149:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
2 stops11h 59mMultiple Airlines
Deal found 4/24$419
Tue 5/149:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/24$430
Wed 5/159:15 pmORD - GCM
1 stop24h 05mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
2 stops11h 59mMultiple Airlines
Deal found 4/24$470
Wed 5/158:09 pmORD - GCM
1 stop25h 11mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
1 stop10h 26mMultiple Airlines
Deal found 4/24$480
Thu 5/167:00 amORD - GCM
2 stops28h 40mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
1 stop10h 26mMultiple Airlines
Deal found 4/24$491
Sat 4/278:35 pmORD - GCM
1 stop15h 35mMultiple Airlines
Wed 5/111:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/24$494
Thu 5/96:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Tue 5/1411:30 amGCM - ORD
2 stops11h 59mMultiple Airlines
Deal found 4/24$509
Thu 5/26:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Thu 5/94:45 pmGCM - ORD
1 stop16h 10mMultiple Airlines
Deal found 4/25$510

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 3,068,701 searches. Data last updated April 26, 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.
Tue 5/149:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
1 stop21h 15mMultiple Airlines
Deal found 4/24$406
Tue 5/149:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
2 stops11h 59mMultiple Airlines
Deal found 4/24$419
Tue 5/149:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
Wed 5/2211:30 amGCM - ORD
1 stop7h 07mMultiple Airlines
Deal found 4/24$430
Wed 5/159:15 pmORD - GCM
1 stop24h 05mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
2 stops11h 59mMultiple Airlines
Deal found 4/24$470
Wed 5/158:09 pmORD - GCM
1 stop25h 11mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
1 stop10h 26mMultiple Airlines
Deal found 4/24$480
Sat 8/108:13 pmMDW - GCM
1 stop22h 27mMultiple Airlines
Wed 8/1411:30 amGCM - MDW
1 stop7h 48mMultiple Airlines
Deal found 4/24$483
Thu 5/167:00 amORD - GCM
2 stops28h 40mMultiple Airlines
Tue 5/2111:30 amGCM - ORD
1 stop10h 26mMultiple Airlines
Deal found 4/24$491
Sat 4/278:35 pmORD - GCM
1 stop15h 35mMultiple Airlines
Wed 5/111:30 amGCM - ORD
1 stop7h 30mMultiple Airlines
Deal found 4/24$494
Thu 5/96:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Tue 5/1411:30 amGCM - ORD
2 stops11h 59mMultiple Airlines
Deal found 4/24$509

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 3,068,701 searches. Data last updated April 26, 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 7/218:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/271:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/25$669
Sun 6/308:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sun 7/72:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/24$679
Sat 6/89:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/151:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/24$704
Sat 6/299:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/61:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/24$744
Sat 5/189:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 5/251:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/24$749
Sun 6/308:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 7/61:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/24$759
Sun 7/288:53 amORD - GCM
Nonstop4h 02mUnited Airlines
Sun 8/42:05 pmGCM - ORD
Nonstop4h 10mUnited Airlines
Deal found 4/25$1,139
Sat 5/119:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 5/181:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/23$1,169
Sat 6/229:28 amORD - GCM
Nonstop4h 02mUnited Airlines
Sat 6/291:50 pmGCM - ORD
Nonstop4h 12mUnited Airlines
Deal found 4/25$1,597

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 3,068,701 searches. Data last updated April 26, 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 5/26:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Thu 5/94:45 pmGCM - ORD
1 stop16h 10mMultiple Airlines
Deal found 4/25$510
Wed 5/17:17 pmMDW - GCM
1 stop26h 03mMultiple Airlines
Sat 5/411:30 amGCM - MDW
2 stops21h 01mMultiple Airlines
Deal found 4/23$520
Thu 5/26:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Thu 5/94:45 pmGCM - ORD
2 stops18h 23mMultiple Airlines
Deal found 4/25$534
Thu 5/26:00 amORD - GCM
1 stop8h 35mMultiple Airlines
Thu 5/94:45 pmGCM - ORD
3 stops30h 44mMultiple Airlines
Deal found 4/25$542
Wed 5/17:50 pmORD - GCM
1 stop25h 30mMultiple Airlines
Sat 5/411:30 amGCM - ORD
2 stops12h 50mMultiple Airlines
Deal found 4/23$556
Thu 5/27:40 amORD - GCM
2 stops13h 40mMultiple Airlines
Thu 5/94:45 pmGCM - ORD
3 stops30h 44mMultiple Airlines
Deal found 4/25$571
Wed 5/17:17 pmMDW - GCM
1 stop26h 03mMultiple Airlines
Sat 5/49:10 amGCM - MDW
1 stop14h 21mMultiple Airlines
Deal found 4/23$575
Wed 5/14:00 pmORD - GCM
1 stop22h 35mMultiple Airlines
Sat 5/49:10 amGCM - ORD
1 stop11h 23mMultiple Airlines
Deal found 4/23$582
Wed 5/19:25 pmORD - GCM
3 stops23h 55mMultiple Airlines
Sat 5/49:10 amGCM - ORD
1 stop11h 23mMultiple Airlines
Deal found 4/23$630

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 3,068,701 searches. Data last updated April 26, 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.
Wed 6/58:27 amMDW - GCM
1 stop7h 43mMultiple Airlines
Deal found 4/25$163
Wed 6/58:50 pmORD - GCM
1 stop24h 30mMultiple Airlines
Deal found 4/25$163
Wed 5/89:25 pmORD - GCM
2 stops23h 55mMultiple Airlines
Deal found 4/25$177
Wed 5/87:00 amORD - GCM
3 stops38h 20mMultiple Airlines
Deal found 4/25$199
Wed 5/84:00 pmORD - GCM
1 stop22h 35mAir Canada
Deal found 4/25$204
Wed 6/511:00 amORD - GCM
1 stop27h 35mAir Canada
Deal found 4/24$205
Wed 6/51:43 pmMDW - GCM
2 stops28h 57mMultiple Airlines
Deal found 4/25$256
Sun 6/238:04 pmORD - GCM
1 stop22h 36mMultiple Airlines
Deal found 4/24$271
Sun 6/237:30 pmORD - GCM
2 stops16h 05mDelta
Deal found 4/24$283

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 3,068,701 searches. Data last updated April 26, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$406 - $593

Route

Depart

Return

Price

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/14

1 stop18h 55m

George Town Owen Roberts Intl

Tue 5/21

1 stop21h 15m

$406

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/14

1 stop18h 55m

George Town Owen Roberts Intl

Tue 5/21

2 stops11h 59m

$419

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Tue 5/14

1 stop18h 55m

George Town Owen Roberts Intl

Wed 5/22

1 stop7h 07m

$430

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

Tue 5/21

2 stops11h 59m

$470

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/15

1 stop27h 35m

George Town Owen Roberts Intl

Thu 5/23

1 stop18h 09m

$535

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 7/25

1 stop8h 35m

George Town Owen Roberts Intl

Thu 8/8

1 stop18h 09m

$552

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

Sun 7/7

1 stop16h 41m

George Town Owen Roberts Intl

Tue 7/16

1 stop8h 51m

$578

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 8/14

1 stop7h 36m

George Town Owen Roberts Intl

Tue 8/20

2 stops10h 16m

$580

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 6/24

1 stop16h 45m

George Town Owen Roberts Intl

Sun 6/30

Nonstop4h 10m

$593

Flights are sorted by cheapest first

Deals found on 4/24

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 26, 2024.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about Air Canada, 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.
Delta
8.1
Very good
10,975 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Delta
8.1
Very good
10,975 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

WestJet
7.5
Good
2,985 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

United Airlines
7.4
Good
11,234 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

American Airlines
7.3
Good
14,898 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

Air Canada
7.0
Good
6,862 reviews
Delta
8.1
Very good
10,975 reviews
Check prices

Entertainment

8.0

Overall

8.1

Comfort

7.9

Food

7.4

Boarding

8.2

Crew

8.6

Reviews

1 / 10

Terrible flight crew that skipped our row for service multiple times.

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 $406, but on average you can expect to pay $502.

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

    Cheapflights has at least 9 direct flights from Chicago to Cayman Islands under $700. A good price for a nonstop flight from Chicago to Cayman Islands is less than $912.

  • Are there last-minute flights available from Chicago to Cayman Islands for under $600?

    There are currently 13+ open flights from Chicago to Cayman Islands within the next 7 days for less than $600.

  • What days are nonstop flights available from Chicago to Cayman Islands?

    Nonstop flights are available for this route on the following days: Friday, Saturday.

  • How many flights depart from Chicago to Cayman Islands on average per day?

    Per day, 2 flights depart from Chicago to Cayman Islands on average.
    Morning (6am - Noon) - 100% of flight departures

  • How long is the flight from Chicago to Cayman Islands?

    A quick flight from Chicago to Cayman Islands can take about 27h 35m. Air Canada provides one of the quickest options available for as low as $535. Airlines will cover a distance of 1622 mi.

  • 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 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?

    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 $480 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 $405.

  • 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 4/25.

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 3,068,701 searches. Data last updated April 26, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$352Average$546FlexibilityNo cancel feeOn-timeN/A
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American AirlinesCheapest$372Average$583FlexibilityNo cancel feeOn-time71%
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United AirlinesCheapest$400Average$644FlexibilityNo cancel feeOn-time69%
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Linear Air TaxiCheapest$18,288Average$51,983FlexibilityNo cancel feeOn-timeN/A
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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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