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Grand Cayman

$169+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jan 27 — Feb 31
Mon 1/27
Mon 2/3
1 adult, Economy
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Cheap flight deals from Chicago to Grand Cayman

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Grand Cayman (zzLAW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 22, 2025.

Round-trip from

$590
(Southwest)

One-way from

$169
(Southwest)
From Chicago (CHI) to Grand Cayman
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One-way flight from Chicago (CHI) to Grand Cayman
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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 January 22, 2025.

This Southwest deal was found by Cheapflights users on 1/20. 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 3/125:00 pmMDW - GCM
2 stops18h 45mSouthwest
Wed 3/1912:40 pmGCM - MDW
2 stops20h 40mSouthwest
Deal found 1/20$576
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Fri 3/75:05 amORD - GCM
1 stop9h 40mMultiple Airlines
Fri 3/144:45 pmGCM - ORD
1 stop28h 48mMultiple Airlines
Deal found 1/21$578
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Wed 3/125:15 amORD - GCM
1 stop10h 10mUnited Airlines
Wed 3/191:50 pmGCM - ORD
Nonstop4h 16mUnited Airlines
Deal found 1/20$590
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Sat 2/154:19 pmMDW - GCM
1 stop22h 51mMultiple Airlines
Wed 2/1911:30 amGCM - MDW
1 stop28h 43mMultiple Airlines
Deal found 1/21$595
This American Airlines deal was found by Cheapflights users on 1/21. 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 3/236:58 pmORD - GCM
1 stop16h 02mAmerican Airlines
Thu 3/273:00 pmGCM - ORD
1 stop9h 18mAmerican Airlines
Deal found 1/21$600
This Delta deal was found by Cheapflights users on 1/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/126:00 amMDW - GCM
1 stop5h 38mDelta
Wed 3/191:03 pmGCM - MDW
1 stop9h 20mDelta
Deal found 1/20$600
This CheapOair deal was found by Cheapflights users on 1/21. 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.
Sun 6/18:25 pmORD - GCM
1 stop15h 30mAir Canada
Thu 6/512:45 pmGCM - ORD
2 stops19h 20mAir Canada
Deal found 1/21$603
This Delta deal was found by Cheapflights users on 1/21. 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 2/265:45 amORD - GCM
1 stop5h 53mDelta
Tue 3/111:03 pmGCM - ORD
1 stop10h 53mDelta
Deal found 1/21$610
This Mytrip deal was found by Cheapflights users on 1/21. 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 2/2310:19 amMDW - GCM
2 stops26h 24mWestJet
Sun 3/22:50 pmGCM - MDW
3 stops22h 52mWestJet
Deal found 1/21$1,012

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 January 22, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 3/12

5:00 pm-11:45 am

2 stops18h 45m

George Town Owen Roberts Intl

Wed 3/19

12:40 pm-9:20 am

2 stops20h 40m

$576

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 3/7

5:05 am-3:45 pm

1 stop9h 40m

George Town Owen Roberts Intl

Fri 3/14

4:45 pm-9:33 pm

1 stop28h 48m

$578

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 3/12

5:15 am-3:25 pm

1 stop10h 10m

George Town Owen Roberts Intl

Wed 3/19

1:50 pm-6:06 pm

Nonstop4h 16m

$590

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sat 2/15

4:19 pm-4:10 pm

1 stop22h 51m

George Town Owen Roberts Intl

Wed 2/19

11:30 am-3:13 pm

1 stop28h 43m

$595

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 3/23

6:58 pm-11:00 am

1 stop16h 02m

George Town Owen Roberts Intl

Thu 4/3

3:00 pm-8:25 am

1 stop17h 25m

$600

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 3/12

6:00 am-11:38 am

1 stop5h 38m

George Town Owen Roberts Intl

Wed 3/19

1:03 pm-10:23 pm

1 stop9h 20m

$600

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 6/1

3:40 pm-11:55 am

2 stops20h 15m

George Town Owen Roberts Intl

Thu 6/5

12:45 pm-8:05 am

2 stops19h 20m

$603

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 2/26

5:45 am-12:38 pm

1 stop5h 53m

George Town Owen Roberts Intl

Tue 3/11

1:03 pm-11:56 pm

1 stop10h 53m

$610

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Fri 3/7

7:10 pm-11:15 am

2 stops15h 05m

George Town Owen Roberts Intl

Sat 3/15

1:10 pm-9:25 am

2 stops20h 15m

$800

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/23

10:25 am-12:43 pm

3 stops26h 18m

George Town Owen Roberts Intl

Mon 3/31

1:50 pm-6:18 pm

2 stops28h 28m

$826

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 22 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.

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 January 22, 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 January 22, 2025.
Get a feel of what it's like to fly with Southwest, American Airlines and Delta 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
4,654 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,654 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,512 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,975 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

WestJet
7.2
Good
2,829 reviews
Southwest
8.1
Very good
4,654 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Food

7.2

Overall

8.1

Entertainment

7.7

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Southwest. According to our data, you can fly for as low as $169. Users have also found prices from $189 and $231 on Sun Country Air and Air Canada, respectively.

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

    On average you can expect to pay $575 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 $462.

  • 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
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 January 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$373Average$532FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$436Average$633FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$461Average$697FlexibilityNo cancel feeOn-time69%
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