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Grand Cayman

$163+ 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 3/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$601
(Kiwi.com)

One-way from

$163
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$660
Provider with most accurate pricing for Chicago (CHI)-George Town Owen Roberts Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago (CHI)-George Town Owen Roberts Intl flights.
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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. 8% potential increase in price ($63 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/305:01 amMDW - GCM
1 stop11h 09mMultiple Airlines
Sun 4/61:50 pmGCM - MDW
1 stop20h 30mMultiple Airlines
Deal found 2/18$601
This American Airlines deal was found by Cheapflights users on 2/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/236:30 pmORD - GCM
1 stop17h 15mAmerican Airlines
Thu 4/312:00 pmGCM - ORD
1 stop12h 20mAmerican Airlines
Deal found 2/20$610
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/252:00 pmORD - GCM
1 stop21h 55mMultiple Airlines
Sat 5/3111:30 amGCM - ORD
3 stops34h 58mMultiple Airlines
Deal found 2/19$615
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/118:45 pmMDW - GCM
2 stops15h 05mSouthwest
Wed 6/2512:45 pmGCM - MDW
2 stops8h 55mSouthwest
Deal found 2/20$616
This United Airlines deal was found by Cheapflights users on 2/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/68:45 amORD - GCM
Nonstop3h 55mUnited Airlines
Sun 4/131:45 pmGCM - ORD
Nonstop4h 22mUnited Airlines
Deal found 2/20$620
This Priceline deal was found by Cheapflights users on 2/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/226:15 pmORD - GCM
2 stops17h 40mAir Canada
Thu 6/2612:50 pmGCM - ORD
2 stops19h 05mAir Canada
Deal found 2/20$632
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/146:00 amMDW - GCM
1 stop5h 38mDelta
Tue 3/181:03 pmGCM - MDW
1 stop9h 20mDelta
Deal found 2/19$725
This Southwest deal was found by Cheapflights users on 2/20. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/155:25 pmORD - GCM
2 stops18h 25mSouthwest
Fri 6/2012:45 pmGCM - ORD
2 stops20h 40mSouthwest
Deal found 2/20$730
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/55:45 amORD - GCM
1 stop5h 53mDelta
Wed 3/191:03 pmGCM - ORD
1 stop10h 53mDelta
Deal found 2/19$740
This WestJet deal was found by Cheapflights users on 2/20. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/612:48 pmMDW - GCM
2 stops23h 55mWestJet
Sun 4/131:50 pmGCM - MDW
2 stops43h 17mWestJet
Deal found 2/20$3,164

Find flights from Chicago to Grand Cayman within your budget

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 February 20, 2025.

Fly from

Chicago

Fly to

Grand Cayman

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/30

5:01 am-4:10 pm

1 stop11h 09m

George Town Owen Roberts Intl

Sun 4/6

1:50 pm-10:20 am

1 stop20h 30m

$601

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/23

6:30 pm-11:45 am

1 stop17h 15m

George Town Owen Roberts Intl

Thu 4/3

12:00 pm-12:20 am

1 stop12h 20m

$610

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 6/11

8:45 pm-11:50 am

2 stops15h 05m

George Town Owen Roberts Intl

Wed 6/25

12:45 pm-9:40 pm

2 stops8h 55m

$616

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 3/20

9:57 pm-11:40 am

2 stops13h 43m

George Town Owen Roberts Intl

Thu 3/27

2:00 pm-11:37 pm

1 stop9h 37m

$616

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/6

8:45 am-12:40 pm

Nonstop3h 55m

George Town Owen Roberts Intl

Sun 4/13

1:45 pm-6:07 pm

Nonstop4h 22m

$620

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 4/12

3:35 pm-1:30 pm

2 stops21h 55m

George Town Owen Roberts Intl

Thu 4/17

2:30 pm-8:00 pm

2 stops29h 30m

$670

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 3/14

6:00 am-11:38 am

1 stop5h 38m

George Town Owen Roberts Intl

Tue 3/18

1:03 pm-10:23 pm

1 stop9h 20m

$725

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 3/5

5:45 am-12:38 pm

1 stop5h 53m

George Town Owen Roberts Intl

Wed 3/19

1:03 pm-11:56 pm

1 stop10h 53m

$740

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/6

4:45 pm-12:43 pm

2 stops19h 58m

George Town Owen Roberts Intl

Sun 4/13

1:50 pm-3:56 pm

2 stops26h 06m

$1,652

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 4/6

12:48 pm-12:43 pm

2 stops23h 55m

George Town Owen Roberts Intl

Sun 4/13

1:50 pm-9:07 am

2 stops43h 17m

$3,164

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

Showing 1-10 of 17 results
1
2

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.

Travel insights for flights from Chicago to Grand Cayman

Get recent, data-driven insights about flights from Chicago to Grand Cayman including ideal travel times, pricing trends, and more.

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 February 20, 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 February 20, 2025.
Get a feel of what it's like to fly with Southwest, Delta and United Airlines from Chicago to Grand Cayman by reading reviews from past customers. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,219 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,765 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

WestJet
7.2
Good
2,801 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Entertainment

7.6

Food

7.1

Overall

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $211. Users have also found prices from $217 and $293 on Southwest and Delta, respectively.

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

    On average you can expect to pay $578 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 $450.

  • 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

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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
St. Louis to George Town flights
Midway 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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$424Average$583FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$468Average$662FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$514Average$703FlexibilityNo cancel feeOn-time69%
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