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Grand Cayman

$95+ 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:26 pmORD - GCM
1 stop21h 19mSpirit Airlines
Thu 1/82:49 pmGCM - ORD
1 stop7h 14mSpirit Airlines
Deal found 12/3$293
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/313:26 pmORD - GCM
1 stop21h 19mMultiple Airlines
Thu 1/82:49 pmGCM - ORD
2 stops24h 42mMultiple Airlines
Deal found 12/3$321
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/178:00 amORD - GCM
2 stops28h 45mMultiple Airlines
Sun 12/212:40 pmGCM - ORD
1 stop10h 46mMultiple Airlines
Deal found 12/4$333
This Mytrip deal was found by Cheapflights users on 12/2. 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.
Wed 12/249:09 pmORD - GCM
2 stops15h 36mSpirit Airlines
Sun 12/282:40 pmGCM - ORD
1 stop10h 50mSpirit Airlines
Deal found 12/2$345
This Expedia deal was found by Cheapflights users on 12/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/255:00 amORD - GCM
1 stop7h 45mSpirit Airlines
Sat 1/102:34 pmGCM - ORD
1 stop7h 29mSpirit Airlines
Deal found 12/3$352
This Expedia deal was found by Cheapflights users on 12/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/75:00 amORD - GCM
1 stop7h 45mSpirit Airlines
Sun 12/142:40 pmGCM - ORD
1 stop10h 29mSpirit Airlines
Deal found 12/3$354
This Mytrip deal was found by Cheapflights users on 12/2. 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.
Wed 12/246:05 pmORD - GCM
1 stop16h 30mMultiple Airlines
Sun 12/282:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Deal found 12/2$360
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2012:39 pmORD - GCM
2 stops24h 06mMultiple Airlines
Thu 12/252:40 pmGCM - ORD
1 stop10h 50mMultiple Airlines
Deal found 12/3$379
This FlightHub deal was found by Cheapflights users on 12/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:00 amORD - GCM
1 stop7h 45mSpirit Airlines
Sat 12/275:56 pmGCM - ORD
1 stop7h 34mSpirit Airlines
Deal found 12/2$382
This Mytrip deal was found by Cheapflights users on 12/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/93:26 pmORD - GCM
3 stops23h 39mMultiple Airlines
Thu 12/112:40 pmGCM - ORD
1 stop10h 29mMultiple Airlines
Deal found 12/3$394
This Kiwi.com deal was found by Cheapflights users on 12/2. 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.
Tue 12/167:44 amMDW - GCM
2 stops12h 31mMultiple Airlines
Tue 12/234:45 pmGCM - MDW
1 stop22h 52mMultiple Airlines
Deal found 12/2$417
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/72:59 pmMDW - GCM
1 stop19h 36mMultiple Airlines
Sun 12/142:40 pmGCM - MDW
2 stops43h 06mMultiple Airlines
Deal found 12/3$432

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 December 4, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$245
(Expedia)

One-way from

$95
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$803
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. 7% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($14 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 4, 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

MDW - GCM

MDWGCM

Chicago Midway

Mon 1/12

3:01 pm-4:05 pm

1 stop24h 04m

George Town Owen Roberts Intl

Sat 1/17

2:34 pm-8:03 am

2 stops18h 29m

$331

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 3/5

6:30 am-9:15 pm

1 stop13h 45m

George Town Owen Roberts Intl

Mon 3/9

7:00 am-3:33 pm

1 stop8h 33m

$409

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 3/13

8:00 am-10:05 pm

1 stop14h 05m

George Town Owen Roberts Intl

Thu 3/19

7:00 am-3:33 pm

1 stop8h 33m

$427

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Wed 12/31

5:05 am-12:35 pm

1 stop6h 30m

George Town Owen Roberts Intl

Thu 1/8

1:50 pm-10:05 pm

2 stops9h 15m

$434

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/31

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Thu 1/8

2:50 pm-6:04 pm

Nonstop4h 14m

$438

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 3/25

7:35 am-3:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Wed 4/1

1:50 pm-6:13 pm

Nonstop4h 23m

$442

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Fri 1/30

5:00 am-12:55 pm

1 stop6h 55m

George Town Owen Roberts Intl

Mon 2/2

1:50 pm-9:00 pm

1 stop8h 10m

$446

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 5/3

5:05 am-11:55 am

1 stop6h 50m

George Town Owen Roberts Intl

Sat 5/9

1:15 pm-8:25 pm

1 stop7h 10m

$446

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

5:30 am-2:27 pm

1 stop7h 57m

George Town Owen Roberts Intl

Wed 12/31

1:52 pm-12:02 am

1 stop11h 10m

$452

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 4/26

6:00 am-11:24 am

1 stop5h 24m

George Town Owen Roberts Intl

Wed 4/29

12:45 pm-11:55 pm

1 stop11h 10m

$452

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 42 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, December is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $339). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $650). 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 December 4, 2025.

A simple way to save on the total cost of your ticket is to fly from Chicago to Grand Cayman at noon. If you’re flexible enough to do this you can expect to save up to 40% on your trip compared to booking a flight in the morning.

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 December 4, 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
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,250 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,011 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,066 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,047 reviews
Southwest
8.0
Very good
4,250 reviews

Crew

8.6

Food

7.0

Comfort

8.0

Overall

8.0

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 4h. Southwest provides one of the quickest options available for as low as $438. The distance between Chicago and Grand Cayman is about 1613 mi. This flight may include one or multiple stops.

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

    On average you can expect to pay $596 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $339 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $245.

  • 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 $339). Flying from Chicago to Grand Cayman in September is currently the most expensive (average of $650). 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 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$341Average$697FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$467Average$720FlexibilityNo cancel feeOn-time71%

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