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$166+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
jul. 30 — ago. 61
From?
To?
mar. 7/30
mar. 8/6
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 82% by booking at least 22 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 $671.

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

October is one of the best times of the year to fly to Cayman Islands from Chicago. Prices for October average $569 per person but you can even find prices for as low as $384. The most expensive prices can be found in the month of March. Opting for a October flight can save you 25% on your journey compared to booking in March

What is the cheapest time of day to fly from CHI to 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 Chicago to Cayman Islands flights in July & August 2024

Find cheap flight options from Chicago to Cayman Islands specifically for the months of July and August 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,752,877 searches. Prices were last updated on julio 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in July and August 2024. More deals are always being added, so be sure to check back regularly.
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
sáb. 8/246:50 amORD - GCM
2 stops8h 00mMultiple Airlines
sáb. 8/319:10 amGCM - ORD
1 stop9h 31mMultiple Airlines
Deal found 7/25$477
This Kiwi.com deal was found by Cheapflights users on 7/25. 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. 8/157:31 pmORD - GCM
1 stop16h 09mMultiple Airlines
lun. 8/199:30 amGCM - ORD
1 stop24h 20mMultiple Airlines
Deal found 7/25$481
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
vie. 8/237:31 pmORD - GCM
2 stops19h 19mMultiple Airlines
mié. 8/2811:30 amGCM - ORD
1 stop7h 11mMultiple Airlines
Deal found 7/25$482
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
vie. 8/236:50 amORD - GCM
1 stop14h 30mMultiple Airlines
mié. 8/2811:30 amGCM - ORD
1 stop7h 11mMultiple Airlines
Deal found 7/25$494
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/157:31 pmORD - GCM
1 stop16h 09mMultiple Airlines
lun. 8/199:30 amGCM - ORD
3 stops30h 33mMultiple Airlines
Deal found 7/25$504
This Delta deal was found by Cheapflights users on 7/25. 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.
jue. 8/227:59 pmORD - GCM
1 stop15h 31mDelta
jue. 8/2912:50 pmGCM - ORD
1 stop8h 27mDelta
Deal found 7/25$513
This Delta deal was found by Cheapflights users on 7/25. 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.
jue. 8/227:20 pmORD - GCM
2 stops16h 10mDelta
jue. 8/2912:50 pmGCM - ORD
1 stop11h 04mDelta
Deal found 7/25$518
This mytrip.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/157:55 amORD - GCM
3 stops27h 45mMultiple Airlines
lun. 8/199:30 amGCM - ORD
3 stops30h 33mMultiple Airlines
Deal found 7/25$523
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
mié. 8/147:31 pmORD - GCM
1 stop25h 49mMultiple Airlines
dom. 8/182:00 pmGCM - ORD
1 stop19h 50mMultiple Airlines
Deal found 7/24$535

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 2,752,877 searches. Data last updated julio 25, 2024.
The lowest fares we've come across on flights traveling from Chicago to Cayman Islands in July and August 2024. More deals are always being added, so be sure to check back regularly.
This Delta deal was found by Cheapflights users on 7/23. 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.
dom. 11/106:00 amORD - GCM
1 stop5h 30mDelta
mar. 11/191:55 pmGCM - ORD
1 stop11h 04mDelta
Deal found 7/23$438
This Delta deal was found by Cheapflights users on 7/23. 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.
dom. 11/106:00 amMDW - GCM
1 stop5h 30mDelta
mar. 11/191:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 7/23$438
This Delta deal was found by Cheapflights users on 7/24. 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.
lun. 9/166:00 amORD - GCM
1 stop5h 31mDelta
jue. 9/1912:53 pmGCM - ORD
2 stops18h 33mDelta
Deal found 7/24$443
This Delta deal was found by Cheapflights users on 7/23. 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.
lun. 11/111:10 pmMDW - GCM
2 stops22h 20mDelta
vie. 11/151:55 pmGCM - MDW
1 stop8h 49mDelta
Deal found 7/23$443
This American Airlines deal was found by Cheapflights users on 7/24. 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. 12/318:20 amORD - GCM
1 stop6h 35mAmerican Airlines
mar. 1/74:17 pmGCM - ORD
1 stop20h 50mAmerican Airlines
Deal found 7/24$450
This American Airlines deal was found by Cheapflights users on 7/23. 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.
sáb. 12/146:54 pmORD - GCM
1 stop15h 56mAmerican Airlines
sáb. 12/213:44 pmGCM - ORD
Nonstop4h 11mAmerican Airlines
Deal found 7/23$453
This American Airlines deal was found by Cheapflights users on 7/24. 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. 12/316:35 amORD - GCM
2 stops8h 20mAmerican Airlines
mar. 1/74:17 pmGCM - ORD
1 stop20h 50mAmerican Airlines
Deal found 7/24$455
This American Airlines deal was found by Cheapflights users on 7/23. 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.
lun. 12/166:54 pmORD - GCM
1 stop15h 56mAmerican Airlines
lun. 12/231:45 pmGCM - ORD
1 stop6h 47mAmerican Airlines
Deal found 7/23$462
This Delta deal was found by Cheapflights users on 7/23. 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.
jue. 11/76:00 amORD - GCM
1 stop5h 30mDelta
vie. 11/151:55 pmGCM - ORD
1 stop8h 09mDelta
Deal found 7/23$463

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 2,752,877 searches. Data last updated julio 25, 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.
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
mié. 7/317:50 pmORD - GCM
1 stop25h 30mMultiple Airlines
mié. 8/75:10 pmGCM - ORD
1 stop14h 44mMultiple Airlines
Deal found 7/24$558
This CheapOair deal was found by Cheapflights users on 7/23. 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.
dom. 8/46:00 amORD - GCM
1 stop8h 35mAir Canada
dom. 8/113:45 pmGCM - ORD
2 stops27h 10mAir Canada
Deal found 7/23$560
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
mié. 7/317:50 pmORD - GCM
1 stop25h 30mMultiple Airlines
mié. 8/75:10 pmGCM - ORD
2 stops25h 20mMultiple Airlines
Deal found 7/24$576
This Orbitz deal was found by Cheapflights users on 7/23. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/46:00 amORD - GCM
1 stop8h 35mAir Canada
dom. 8/113:45 pmGCM - ORD
1 stop23h 09mAir Canada
Deal found 7/23$600
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/316:19 pmORD - GCM
3 stops27h 01mMultiple Airlines
mié. 8/75:10 pmGCM - ORD
1 stop14h 44mMultiple Airlines
Deal found 7/24$621
This Kiwi.com deal was found by Cheapflights users on 7/24. 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. 7/309:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
lun. 8/59:30 amGCM - ORD
1 stop23h 06mMultiple Airlines
Deal found 7/24$677
This Kiwi.com deal was found by Cheapflights users on 7/24. 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. 7/309:15 pmORD - GCM
1 stop18h 55mMultiple Airlines
lun. 8/59:30 amGCM - ORD
1 stop23h 06mMultiple Airlines
Deal found 7/24$680
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 7/3011:13 amORD - GCM
3 stops28h 57mMultiple Airlines
lun. 8/59:30 amGCM - ORD
1 stop7h 00mMultiple Airlines
Deal found 7/24$685
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
vie. 8/210:02 amORD - GCM
1 stop11h 18mMultiple Airlines
lun. 8/59:30 amGCM - ORD
1 stop23h 06mMultiple Airlines
Deal found 7/24$689

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 2,752,877 searches. Data last updated julio 25, 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.
This mytrip.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure mytrip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/246:50 amORD - GCM
2 stops8h 00mMultiple Airlines
Deal found 7/24$166
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
mié. 8/217:31 pmORD - GCM
1 stop25h 49mMultiple Airlines
Deal found 7/24$167
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
mié. 8/217:31 pmORD - GCM
1 stop25h 49mMultiple Airlines
Deal found 7/25$168
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
mié. 10/237:00 amORD - GCM
1 stop9h 10mMultiple Airlines
Deal found 7/24$174
This Kiwi.com deal was found by Cheapflights users on 7/24. 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. 9/247:00 amORD - GCM
1 stop9h 10mMultiple Airlines
Deal found 7/24$175
This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
sáb. 9/217:00 amORD - GCM
1 stop9h 10mMultiple Airlines
Deal found 7/23$176
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
sáb. 9/147:00 amORD - GCM
1 stop9h 10mMultiple Airlines
Deal found 7/25$179
This Kiwi.com deal was found by Cheapflights users on 7/25. 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.
sáb. 9/147:00 amORD - GCM
2 stops7h 50mMultiple Airlines
Deal found 7/25$180
This Kiwi.com deal was found by Cheapflights users on 7/24. 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. 8/227:31 pmORD - GCM
1 stop16h 09mMultiple Airlines
Deal found 7/24$184

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 2,752,877 searches. Data last updated julio 25, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$438 - $542

Route

Depart

Return

Price

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 11/10

1 stop5h 30m

George Town Owen Roberts Intl

vie. 11/15

1 stop8h 09m

$438

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

dom. 11/10

1 stop5h 30m

George Town Owen Roberts Intl

vie. 11/15

1 stop8h 49m

$438

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

lun. 9/16

1 stop5h 31m

George Town Owen Roberts Intl

jue. 9/19

2 stops18h 33m

$443

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mar. 12/31

1 stop6h 35m

George Town Owen Roberts Intl

mar. 1/7

1 stop20h 50m

$450

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 1/4

1 stop13h 53m

George Town Owen Roberts Intl

sáb. 1/11

Nonstop4h 11m

$453

Chicago MidwayGeorge Town Owen Roberts Intl

MDW - GCM

MDWGCM

Chicago Midway

sáb. 11/2

1 stop22h 27m

George Town Owen Roberts Intl

sáb. 11/9

1 stop11h 08m

$471

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 8/23

2 stops19h 19m

George Town Owen Roberts Intl

mié. 8/28

1 stop7h 11m

$482

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 11/6

1 stop6h 35m

George Town Owen Roberts Intl

sáb. 11/16

Nonstop4h 16m

$498

Chicago O'Hare IntlGeorge Town Owen Roberts Intl

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 12/5

2 stops22h 40m

George Town Owen Roberts Intl

jue. 12/12

2 stops21h 14m

$542

Flights are sorted by cheapest first

Deals found on 7/23

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

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.

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 julio 25, 2024.
To help decide which airline to fly from Chicago to Cayman Islands, see what other customers have to say about Delta, 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
8.0
Very good
9,630 reviews

Boarding

8.2

Food

7.4

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Delta
8.0
Very good
9,630 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Food

7.4

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

United Airlines
7.4
Good
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Food

7.4

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

WestJet
7.4
Good
2,761 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Food

7.4

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

American Airlines
7.3
Good
10,000 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Food

7.4

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

Air Canada
6.9
Okay
7,353 reviews
Delta
8.0
Very good
9,630 reviews

Boarding

8.2

Food

7.4

Comfort

7.9

Overall

8.0

Entertainment

8.0

Crew

8.6

Reviews

1 / 10

One of the worst flights ever. I got to the airport early for my 6:48 pm flight and tried to get on the 4:30 ish flight. The gate agent was one of the worst customer service people in my 20 yrs of flying Delta. Very rude and wouldn’t even talk to me about riding standby. Then flight took off 3 hrs late and when Landed in Atlanta, the gate people wouldn’t even try to get me on the plane. It was still there but door was closed. For all of my almost 2 million miles, the worst experience from Delta. I am highly disappointed as it was not my fault I have to sleep in Atlanta and not Jacksonville Florida

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 Delta for just $438, but on average you can expect to pay $462.

  • Are there nonstop flights from Chicago to Cayman Islands for under $500 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Cayman Islands under $500. A good price for a nonstop flight from Chicago to Cayman Islands is less than $1,051.

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

    There are currently 20+ open flights from Chicago to Cayman Islands within the next 7 days for less than $600.

  • 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 $572 for a flight from Chicago to Cayman Islands. The cheapest flight overall is $453 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 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 7/24.

  • 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 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 $454). Flying from Chicago to Cayman Islands in June is currently the most expensive (average of $558). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Alternative routes for Chicago to Cayman Islands
See prices for flight routes from nearby airports that may be better suited for you.

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Top 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 2,752,877 searches. Data last updated julio 25, 2024.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$351Average$527FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$371Average$576FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$403Average$643FlexibilityNo cancel feeOn-time69%
Linear Air TaxiCheapest$18,288Average$51,983FlexibilityNo cancel feeOn-timeN/A
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