HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Grand Cayman

$104+ 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 12/11. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Grand Cayman with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 14, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$342
(United Airlines)

One-way from

$104
(Priceline)

Popular in

December

Cheapest in

October

Average price

$539
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. 10% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

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 October 14, 2025.

This United Airlines deal was found by Cheapflights users on 10/13. 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.
Mon 12/157:35 amORD - GCM
1 stop7h 55mUnited Airlines
Fri 12/192:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 10/13$342
This Travelocity deal was found by Cheapflights users on 10/14. 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.
Sun 11/306:05 pmORD - GCM
2 stops41h 20mMultiple Airlines
Sat 12/65:56 pmGCM - ORD
1 stop7h 23mMultiple Airlines
Deal found 10/14$344
This Travelocity deal was found by Cheapflights users on 10/13. 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.
Sun 11/307:20 amORD - GCM
2 stops52h 05mMultiple Airlines
Sun 12/72:35 pmGCM - ORD
1 stop6h 26mMultiple Airlines
Deal found 10/13$348
This Mytrip deal was found by Cheapflights users on 10/12. 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 12/34:58 pmORD - GCM
2 stops19h 47mSpirit Airlines
Sun 12/72:40 pmGCM - ORD
1 stop6h 21mSpirit Airlines
Deal found 10/12$362
This Priceline deal was found by Cheapflights users on 10/12. 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.
Wed 10/2910:00 amORD - GCM
1 stop25h 25mAir Canada
Fri 10/3112:30 pmGCM - ORD
1 stop9h 35mAir Canada
Deal found 10/12$367
This American Airlines deal was found by Cheapflights users on 10/12. 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 12/147:00 amORD - GCM
1 stop6h 44mAmerican Airlines
Sun 12/213:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 10/12$372
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Thu 11/277:10 amORD - GCM
1 stop8h 20mUnited Airlines
Thu 12/45:45 pmGCM - ORD
1 stop17h 17mUnited Airlines
Deal found 10/12$374
This United Airlines deal was found by Cheapflights users on 10/12. 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.
Tue 11/118:50 amORD - GCM
1 stop6h 40mUnited Airlines
Tue 11/185:45 pmGCM - ORD
1 stop7h 30mUnited Airlines
Deal found 10/12$375
This American Airlines deal was found by Cheapflights users on 10/13. 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.
Sat 12/67:07 pmORD - GCM
1 stop16h 03mAmerican Airlines
Sat 12/131:01 pmGCM - ORD
1 stop8h 33mAmerican Airlines
Deal found 10/13$377
This Delta deal was found by Cheapflights users on 10/12. 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.
Thu 11/276:00 amMDW - GCM
1 stop5h 35mDelta
Thu 12/41:50 pmGCM - MDW
1 stop10h 59mDelta
Deal found 10/12$377
This Southwest deal was found by Cheapflights users on 10/14. 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 11/95:50 amMDW - GCM
1 stop5h 45mSouthwest
Tue 11/111:30 pmGCM - MDW
1 stop7h 00mSouthwest
Deal found 10/14$463
This Kiwi.com deal was found by Cheapflights users on 10/13. 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 12/318:00 amMDW - GCM
2 stops26h 35mMultiple Airlines
Tue 1/611:30 amGCM - MDW
1 stop28h 17mMultiple Airlines
Deal found 10/13$478

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 October 14, 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 12/3

7:35 am-4:30 pm

1 stop7h 55m

George Town Owen Roberts Intl

Wed 12/10

5:45 pm-12:15 am

1 stop7h 30m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/21

5:50 am-12:35 pm

1 stop5h 45m

George Town Owen Roberts Intl

Sun 1/25

2:00 pm-11:54 pm

1 stop10h 54m

$365

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Thu 11/13

7:10 am-4:30 pm

1 stop8h 20m

George Town Owen Roberts Intl

Tue 11/18

5:45 pm-12:15 am

1 stop7h 30m

$375

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Thu 11/27

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 12/4

1:50 pm-11:49 pm

1 stop10h 59m

$377

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sun 11/16

6:00 am-4:30 pm

1 stop9h 30m

George Town Owen Roberts Intl

Sun 11/23

5:45 pm-12:15 am

1 stop7h 30m

$400

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 1/21

1:35 pm-1:40 pm

3 stops23h 05m

George Town Owen Roberts Intl

Sun 1/25

2:35 pm-11:42 pm

1 stop10h 07m

$402

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Mon 1/26

4:25 pm-12:55 pm

2 stops19h 30m

George Town Owen Roberts Intl

Fri 1/30

1:50 pm-9:50 pm

1 stop9h 00m

$424

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

Sun 3/1

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

Thu 3/5

2:00 pm-9:46 pm

1 stop8h 46m

$430

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Sat 1/17

5:50 am-1:47 pm

1 stop6h 57m

George Town Owen Roberts Intl

Sat 1/24

12:25 pm-8:38 pm

2 stops9h 13m

$434

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

Wed 12/24

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

Wed 12/31

2:50 pm-6:04 pm

Nonstop4h 14m

$442

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Showing 1-10 of 29 results
1
2
3

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 $394). 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 October 14, 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 41% 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 October 14, 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
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,975 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,976 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,042 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 5h 45m. United Airlines provides one of the quickest options available for as low as $365. The distance between Chicago and Grand Cayman is about 1613 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 Spirit Airlines. According to our data, you can fly for as low as $108. Users have also found prices from $136 and $157 on Air Canada and Southwest, respectively.

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

    On average you can expect to pay $555 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $220 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $326.

  • 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 $394). 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

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

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 October 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$500Average$706FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$503Average$728FlexibilityNo cancel feeOn-time69%
DeltaCheapest$564Average$798FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.