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Grand Cayman

$156+ 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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
1 adult, Economy
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Cheap 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 July 3, 2025.

Round-trip from

$452
(Orbitz)

One-way from

$156
(Trip.com)

Popular in

March

Cheapest in

September

Average price

$603
From Chicago (CHI) to Grand Cayman
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One-way flight from Chicago (CHI) to Grand Cayman
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Highest demand for flights based on searches. 11% potential increase in price ($82 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($20 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Find 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 July 3, 2025.

This Orbitz deal was found by Cheapflights users on 7/2. 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.
Fri 10/246:06 pmORD - GCM
2 stops41h 14mAir Canada
Fri 10/3112:30 pmGCM - ORD
1 stop28h 58mAir Canada
Deal found 7/2$452
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Wed 7/238:09 amORD - GCM
1 stop27h 31mMultiple Airlines
Mon 7/284:45 pmGCM - ORD
1 stop23h 26mMultiple Airlines
Deal found 7/2$460
This Southwest deal was found by Cheapflights users on 7/1. 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.
Mon 11/36:05 amORD - GCM
1 stop5h 30mSouthwest
Fri 11/141:30 pmGCM - ORD
1 stop9h 20mSouthwest
Deal found 7/1$493
This Delta deal was found by Cheapflights users on 7/3. 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.
Wed 12/245:40 amORD - GCM
1 stop5h 50mDelta
Wed 12/313:45 pmGCM - ORD
1 stop9h 13mDelta
Deal found 7/3$520
This Delta deal was found by Cheapflights users on 7/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/51:08 pmMDW - GCM
2 stops22h 34mDelta
Thu 10/91:02 pmGCM - MDW
2 stops19h 43mDelta
Deal found 7/1$524
This American Airlines deal was found by Cheapflights users on 7/2. 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.
Wed 10/155:20 amORD - GCM
2 stops7h 50mAmerican Airlines
Wed 10/2212:25 pmGCM - ORD
1 stop8h 45mAmerican Airlines
Deal found 7/2$525
This Southwest deal was found by Cheapflights users on 7/1. 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.
Thu 7/175:00 amMDW - GCM
1 stop6h 50mSouthwest
Tue 7/2212:45 pmGCM - MDW
1 stop6h 40mSouthwest
Deal found 7/1$573
This Mytrip deal was found by Cheapflights users on 7/2. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/161:43 pmMDW - GCM
3 stops27h 37mMultiple Airlines
Sat 8/231:45 pmGCM - MDW
3 stops23h 18mMultiple Airlines
Deal found 7/2$996

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 July 3, 2025.
Use the filters below to find and compare flights from Chicago to Grand Cayman that are best for you.

Fly from

Chicago

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 7/23

8:09 am-11:40 am

1 stop27h 31m

George Town Owen Roberts Intl

Mon 7/28

4:45 pm-4:11 pm

1 stop23h 26m

$460

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 9/13

3:35 pm-11:55 am

2 stops44h 20m

George Town Owen Roberts Intl

Thu 9/25

12:50 pm-5:33 pm

1 stop28h 43m

$479

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 10/1

7:10 am-11:36 am

2 stops28h 26m

George Town Owen Roberts Intl

Thu 10/9

1:02 pm-7:26 am

2 stops18h 24m

$524

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 10/5

1:08 pm-11:42 am

2 stops22h 34m

George Town Owen Roberts Intl

Thu 10/9

1:02 pm-8:45 am

2 stops19h 43m

$524

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 7/17

5:00 am-11:50 am

1 stop6h 50m

George Town Owen Roberts Intl

Tue 7/22

12:45 pm-7:25 pm

1 stop6h 40m

$573

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 8/16

1:43 pm-5:20 pm

3 stops27h 37m

George Town Owen Roberts Intl

Sat 8/23

1:45 pm-1:03 pm

3 stops23h 18m

$996

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 7/23

8:09 am-4:10 pm

1 stop8h 01m

$156

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 10/1

8:40 am-11:55 am

2 stops27h 15m

$168

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 8/3

5:05 am-11:50 am

1 stop6h 45m

$208

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 7/27

3:58 pm-5:20 pm

1 stop25h 22m

$235

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

Showing 1-10 of 15 results
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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, January is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $467). Flying from Chicago to Grand Cayman in March is currently the most expensive (average of $594). 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 July 3, 2025.

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 July 3, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United 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.
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,270 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,970 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,845 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Air Canada
7.1
Good
9,678 reviews
Southwest
8.0
Very good
4,270 reviews

Entertainment

7.6

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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.

  • 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 $168. Users have also found prices from $208 and $293 on Southwest and Delta, respectively.

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

    On average you can expect to pay $537 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $288 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $460.

  • 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, January is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $467). Flying from Chicago to Grand Cayman in March is currently the most expensive (average of $594). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Grand Cayman

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Town flights
Midway to George Town flights
St. Louis to George Town flights
Moline to George Town flights
O'Hare Intl to Cayman Brac flights

Top 3 airlines flying from Chicago to Grand Cayman

Discover the top 3 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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$463Average$628FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$478Average$669FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$535Average$722FlexibilityNo cancel feeOn-time69%

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