Grand Cayman

$94+ Cheap flights from Chicago (CHI) to Grand Cayman

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 4/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
may. 2 — may. 91
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Cheap flight deals from Chicago to Grand Cayman

Cheapest flights from Chicago to Grand Cayman
Explore the most affordable flight options available from Chicago to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 2, 2026.

This Travelocity deal was found by Cheapflights users on 4/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/206:04 pm
ORD
-
GCM
2 stops41h 21m
Air Canada
jue. 6/2512:25 pm
GCM
-
ORD
1 stop28h 32m
Air Canada
Deal found 4/1$338
This FlightHub deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/45:05 am
ORD
-
GCM
1 stop7h 15m
Spirit Airlines
jue. 4/91:52 pm
GCM
-
ORD
1 stop9h 25m
Spirit Airlines
Deal found 3/30$339
This Expedia deal was found by Cheapflights users on 3/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/59:55 am
ORD
-
GCM
1 stop24h 05m
Air Canada
lun. 6/812:25 pm
GCM
-
ORD
1 stop20h 40m
Air Canada
Deal found 3/31$345
This Expedia deal was found by Cheapflights users on 3/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/125:05 am
ORD
-
GCM
1 stop7h 52m
Multiple Airlines
jue. 4/1611:55 am
GCM
-
ORD
1 stop25h 10m
Multiple Airlines
Deal found 3/28$346
This Travelocity deal was found by Cheapflights users on 3/30. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/218:40 pm
ORD
-
GCM
1 stop14h 45m
Air Canada
lun. 6/2912:25 pm
GCM
-
ORD
1 stop24h 57m
Air Canada
Deal found 3/30$360
This Air Canada deal was found by Cheapflights users on 3/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/298:20 pm
ORD
-
GCM
1 stop13h 40m
Air Canada
jue. 6/412:25 pm
GCM
-
ORD
1 stop20h 40m
Air Canada
Deal found 3/31$363
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/286:00 am
MDW
-
GCM
1 stop6h 10m
Southwest
mar. 5/51:05 pm
GCM
-
MDW
2 stops18h 30m
Southwest
Deal found 3/29$507
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/198:55 pm
MDW
-
GCM
2 stops15h 15m
Southwest
mar. 4/281:05 pm
GCM
-
MDW
2 stops8h 45m
Southwest
Deal found 3/29$528
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/15:35 am
MDW
-
GCM
1 stop6h 35m
Southwest
vie. 5/81:05 pm
GCM
-
MDW
1 stop7h 35m
Southwest
Deal found 3/31$530
This Kiwi.com deal was found by Cheapflights users on 3/28. 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.
lun. 5/116:00 am
MDW
-
GCM
2 stops15h 15m
Multiple Airlines
sáb. 5/161:45 pm
GCM
-
MDW
1 stop20h 00m
Multiple Airlines
Deal found 3/28$552
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/235:35 am
MDW
-
GCM
1 stop6h 35m
Southwest
mié. 4/291:05 pm
GCM
-
MDW
1 stop8h 20m
Southwest
Deal found 4/1$575

Find flight deals from Chicago to Grand Cayman

Keep the following information in mind while searching for Chicago to Grand Cayman flight deals. Data was last updated abril 2, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$345
(Expedia)

One-way from

$94
(Priceline)

Popular in

December

Cheapest in

February

Average price

$637
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
From Chicago (CHI) to Grand Cayman
One-way flight from Chicago (CHI) to Grand Cayman
Highest demand for flights based on searches. 3% potential increase in price ($25 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in April 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Grand Cayman 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 2,558,603 searches. Data last updated abril 2, 2026.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 5/13

7:15 pm-12:10 pm

2 stops16h 55m

George Town Owen Roberts Intl

mié. 5/20

1:05 pm-9:55 pm

1 stop8h 50m

$497

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

mar. 4/28

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

mar. 5/5

1:05 pm-7:45 pm

1 stop6h 40m

$516

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

vie. 5/1

5:35 am-12:10 pm

1 stop6h 35m

George Town Owen Roberts Intl

vie. 5/8

1:05 pm-8:40 pm

1 stop7h 35m

$530

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

vie. 5/1

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

vie. 5/8

1:05 pm-9:55 pm

1 stop8h 50m

$544

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 4/23

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

mié. 4/29

1:05 pm-9:55 pm

1 stop8h 50m

$565

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 5/3

6:38 pm-12:00 pm

2 stops17h 22m

George Town Owen Roberts Intl

vie. 5/29

1:19 pm-8:43 am

2 stops19h 24m

$600

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 5/3

7:45 pm-12:00 pm

1 stop16h 15m

George Town Owen Roberts Intl

vie. 5/29

1:19 pm-10:29 am

2 stops21h 10m

$600

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

jue. 5/14

5:35 am-12:10 pm

1 stop6h 35m

George Town Owen Roberts Intl

jue. 5/21

1:05 pm-8:40 pm

1 stop7h 35m

$603

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 5/3

6:38 pm-12:00 pm

2 stops17h 22m

George Town Owen Roberts Intl

dom. 5/31

1:19 pm-9:09 pm

1 stop7h 50m

$625

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

dom. 5/3

7:43 pm-12:00 pm

2 stops16h 17m

George Town Owen Roberts Intl

dom. 5/31

1:19 pm-9:53 pm

1 stop8h 34m

$625

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/28

Showing 1-10 of 36 resultsSorted by cheapest first
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Best time to book a flight from Chicago to Grand Cayman

Have a flexible travel schedule? Discover the best time to fly to Grand Cayman 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.

Cheapflights Insights

Everything you need to know about your flight from Chicago to Grand Cayman

What is the cheapest month to book a flight from Chicago to Grand Cayman?

Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $322). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $661). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CHI to LAW?

Find hourly flight availability from Chicago to Grand Cayman. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 2, 2026.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Grand Cayman as you normally would.

Reviews of airlines servicing Grand Cayman

Get insights into the airlines that provide service to Grand Cayman. 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 Grand Cayman. Reviews last updated abril 2, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Chicago to Grand Cayman. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Entertainment

7.5

Comfort

8.0

Food

7.0

Overall

8.0

Boarding

8.1

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Chicago to Grand Cayman?

    A quick flight from Chicago to Grand Cayman can take about 16h 55m. Southwest provides one of the quickest options available for as low as $497. The distance between Chicago and Grand Cayman is about 1613 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Chicago to Grand Cayman one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $137. Users have also found prices from $230 and $288 on American Airlines and United Airlines, respectively.

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

    On average you can expect to pay $603 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $230 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $429.

  • Can I find deals for flights from Chicago to Grand Cayman that include hotel bookings?

    Yes. In addition to deals on Chicago to Grand Cayman flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Grand Cayman?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Grand Cayman.

  • Can I find deals for business class flights from Chicago to Grand Cayman?

    Yes. Cheapflights offers flight deals from Chicago to Grand Cayman by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Grand Cayman?

    Currently, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $322). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $661). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Complete your trip

Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.

Top 2 airlines flying from Chicago to Grand Cayman

Discover the top 2 airlines that operate flights from Chicago to Grand Cayman. 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 2,558,603 searches. Data last updated abril 2, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$601FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$429Average$669FlexibilityNo cancel feeOn-time71%

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