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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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Apr 21 — Apr 281
Tue 4/21
Tue 4/28
1 adult, Economy
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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 March 22, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Sun 4/263:57 pm
ORD
-
GCM
1 stop19h 38m
Multiple Airlines
Wed 5/2711:30 am
GCM
-
ORD
1 stop25h 35m
Multiple Airlines
Deal found 3/17$486
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Tue 4/74:51 pm
ORD
-
GCM
1 stop23h 14m
Multiple Airlines
Sun 4/121:52 pm
GCM
-
ORD
1 stop21h 25m
Multiple Airlines
Deal found 3/20$487
This Kiwi.com deal was found by Cheapflights users on 3/20. 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.
Tue 5/196:55 am
ORD
-
GCM
2 stops33h 10m
Multiple Airlines
Wed 5/2711:30 am
GCM
-
ORD
1 stop25h 35m
Multiple Airlines
Deal found 3/20$488
This Orbitz deal was found by Cheapflights users on 3/18. 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.
Sun 5/38:20 pm
ORD
-
GCM
1 stop15h 05m
Air Canada
Thu 5/712:25 pm
GCM
-
ORD
1 stop26h 30m
Air Canada
Deal found 3/18$489
This Expedia deal was found by Cheapflights users on 3/19. 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.
Mon 4/208:31 am
ORD
-
GCM
1 stop29h 27m
Multiple Airlines
Fri 4/2411:10 am
GCM
-
ORD
1 stop28h 05m
Multiple Airlines
Deal found 3/19$490
This Mytrip deal was found by Cheapflights users on 3/18. 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.
Sun 5/38:20 pm
ORD
-
GCM
1 stop15h 05m
Multiple Airlines
Thu 5/77:00 am
GCM
-
ORD
3 stops26h 31m
Multiple Airlines
Deal found 3/18$492
This Air Canada deal was found by Cheapflights users on 3/19. 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.
Sun 5/246:22 pm
ORD
-
GCM
2 stops17h 03m
Air Canada
Sat 5/3010:55 am
GCM
-
ORD
1 stop8h 30m
Air Canada
Deal found 3/19$494
This Mytrip deal was found by Cheapflights users on 3/22. 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 5/26:40 am
ORD
-
GCM
2 stops8h 10m
Multiple Airlines
Sat 5/98:50 am
GCM
-
ORD
2 stops12h 22m
Multiple Airlines
Deal found 3/22$496
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Mon 4/277:50 am
ORD
-
GCM
1 stop13h 25m
Multiple Airlines
Wed 5/2711:30 am
GCM
-
ORD
1 stop25h 35m
Multiple Airlines
Deal found 3/17$497
This Southwest deal was found by Cheapflights users on 3/17. 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 5/115:35 am
MDW
-
GCM
1 stop6h 35m
Southwest
Fri 5/151:05 pm
GCM
-
MDW
1 stop11h 00m
Southwest
Deal found 3/17$498
This Travelocity deal was found by Cheapflights users on 3/20. 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.
Sat 3/288:40 pm
ORD
-
GCM
1 stop14h 15m
Multiple Airlines
Sat 4/41:15 pm
GCM
-
ORD
1 stop6h 36m
Multiple Airlines
Deal found 3/20$499
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/296:08 pm
ORD
-
GCM
2 stops17h 27m
Multiple Airlines
Wed 5/2711:30 am
GCM
-
ORD
1 stop25h 35m
Multiple Airlines
Deal found 3/17$500

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 March 22, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$486
(Kiwi.com)

One-way from

$94
(FlightHub)

Popular in

December

Cheapest in

February

Average price

$685
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
Search Deals
From Chicago (CHI) to Grand Cayman
Search Deals
One-way flight from Chicago (CHI) to Grand Cayman
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($25 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2026
Search Deals

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 March 22, 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

MDW - GCM

MDWGCM

Chicago Midway

Mon 5/11

5:35 am-12:10 pm

1 stop6h 35m

George Town Owen Roberts Intl

Fri 5/15

1:05 pm-12:05 am

1 stop11h 00m

$498

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 5/1

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Fri 5/8

1:05 pm-9:55 pm

1 stop8h 50m

$537

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 5/2

7:45 am-3:00 pm

2 stops7h 15m

George Town Owen Roberts Intl

Sat 5/9

1:05 pm-8:25 pm

1 stop7h 20m

$584

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 5/27

5:55 am-12:10 pm

1 stop6h 15m

George Town Owen Roberts Intl

Tue 6/2

1:05 pm-9:55 pm

1 stop8h 50m

$603

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 4/4

9:35 pm-12:00 pm

2 stops14h 25m

George Town Owen Roberts Intl

Thu 4/9

1:05 pm-12:05 am

1 stop11h 00m

$603

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 5/28

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Mon 6/1

1:05 pm-9:55 pm

1 stop8h 50m

$607

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Tue 4/7

6:00 am-12:10 pm

1 stop6h 10m

George Town Owen Roberts Intl

Tue 4/14

1:05 pm-7:45 pm

1 stop6h 40m

$623

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 5/28

5:30 am-12:10 pm

2 stops6h 40m

George Town Owen Roberts Intl

Mon 6/1

1:05 pm-12:05 am

1 stop11h 00m

$648

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 5/3

9:55 pm-12:10 pm

2 stops14h 15m

George Town Owen Roberts Intl

Sun 5/10

12:50 pm-11:40 pm

2 stops10h 50m

$648

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Mon 6/15

8:50 pm-11:50 am

2 stops15h 00m

George Town Owen Roberts Intl

Sat 6/20

1:05 pm-10:25 pm

1 stop9h 20m

$648

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/21

Showing 1-10 of 34 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 March 22, 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.

Weekly flight availability from Chicago to Grand Cayman

Explore weekly flight availability from Chicago to Grand Cayman. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 22, 2026.

The most flights from CHI to zzLAW are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

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 March 22, 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.
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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.
Southwest
8.0
Very good
4,324 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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.
Delta
7.9
Good
8,314 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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.
United Airlines
7.4
Good
9,455 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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.
American Airlines
7.1
Good
11,489 reviews
Southwest
8.0
Very good
4,324 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Crew

8.6

Comfort

8.0

Entertainment

7.5

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 6h 35m. Southwest provides one of the quickest options available for as low as $498. The distance between Chicago and Grand Cayman is about 1598 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 $599 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 $293.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Complete your trip

Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
George Town Owen Roberts Intl Airport car rentals
George Town car rentals

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 March 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$597FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$429Average$668FlexibilityNo cancel feeOn-time71%

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