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Grand Cayman

$101+ 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 1/31. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — GCM
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
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 noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$272
(Priceline)

One-way from

$101
(Expedia)

Popular in

December

Cheapest in

October

Average price

$804
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. 9% potential increase in price ($72 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in November 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 noviembre 6, 2025.

This Priceline deal was found by Cheapflights users on 11/5. 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.
sáb. 12/67:10 amORD - GCM
1 stop8h 45mSpirit Airlines
sáb. 12/135:56 pmGCM - ORD
1 stop7h 13mSpirit Airlines
Deal found 11/5$272
This Priceline deal was found by Cheapflights users on 11/5. 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.
sáb. 12/67:10 amORD - GCM
1 stop8h 45mSpirit Airlines
jue. 12/112:40 pmGCM - ORD
1 stop6h 21mSpirit Airlines
Deal found 11/5$286
This Expedia deal was found by Cheapflights users on 11/5. 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.
dom. 12/145:00 amORD - GCM
1 stop7h 45mSpirit Airlines
jue. 12/182:40 pmGCM - ORD
1 stop10h 50mSpirit Airlines
Deal found 11/5$305
This Kiwi.com deal was found by Cheapflights users on 11/6. 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.
mié. 12/107:10 amORD - GCM
1 stop29h 35mSpirit Airlines
sáb. 12/135:56 pmGCM - ORD
1 stop7h 13mSpirit Airlines
Deal found 11/6$319
This United Airlines deal was found by Cheapflights users on 11/5. 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.
sáb. 11/298:45 amORD - GCM
Nonstop4h 00mUnited Airlines
sáb. 12/62:50 pmGCM - ORD
Nonstop4h 14mUnited Airlines
Deal found 11/5$338
This American Airlines deal was found by Cheapflights users on 11/5. 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.
dom. 12/145:00 amORD - GCM
1 stop6h 00mAmerican Airlines
dom. 12/213:35 pmGCM - ORD
Nonstop4h 10mAmerican Airlines
Deal found 11/5$347
This United Airlines deal was found by Cheapflights users on 11/6. 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.
sáb. 11/298:45 amORD - GCM
Nonstop4h 00mUnited Airlines
mié. 12/35:45 pmGCM - ORD
1 stop7h 30mUnited Airlines
Deal found 11/6$348
This Delta deal was found by Cheapflights users on 11/5. 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.
sáb. 12/66:00 amMDW - GCM
1 stop5h 30mDelta
mié. 12/101:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 11/5$352
This Delta deal was found by Cheapflights users on 11/5. 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.
sáb. 12/136:00 amMDW - GCM
1 stop5h 30mDelta
mié. 12/171:50 pmGCM - MDW
1 stop10h 57mDelta
Deal found 11/5$385
This Delta deal was found by Cheapflights users on 11/4. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/116:00 amMDW - GCM
1 stop5h 35mDelta
jue. 11/131:50 pmGCM - MDW
1 stop10h 50mDelta
Deal found 11/4$414
This Delta deal was found by Cheapflights users on 11/5. 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.
dom. 12/216:00 amMDW - GCM
1 stop5h 36mDelta
dom. 12/281:52 pmGCM - MDW
1 stop9h 30mDelta
Deal found 11/5$443
This Kiwi.com deal was found by Cheapflights users on 11/5. 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.
vie. 12/128:42 pmMDW - GCM
2 stops19h 13mMultiple Airlines
mar. 12/165:50 pmGCM - MDW
1 stop17h 15mMultiple Airlines
Deal found 11/5$471

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 noviembre 6, 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

jue. 12/25

8:50 am-4:35 pm

1 stop6h 45m

George Town Owen Roberts Intl

mié. 12/31

2:50 pm-6:04 pm

Nonstop4h 14m

$342

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

dom. 12/14

6:00 am-12:35 pm

1 stop5h 35m

George Town Owen Roberts Intl

mié. 12/24

3:42 pm-10:22 pm

1 stop7h 40m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

sáb. 12/13

8:45 am-4:35 pm

1 stop6h 50m

George Town Owen Roberts Intl

mié. 12/17

5:45 pm-12:15 am

1 stop7h 30m

$352

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 11/27

5:23 am-12:35 pm

1 stop6h 12m

George Town Owen Roberts Intl

mié. 12/3

1:50 pm-10:00 am

2 stops21h 10m

$357

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

mié. 11/26

8:02 pm-12:35 pm

1 stop15h 33m

George Town Owen Roberts Intl

mié. 12/3

1:50 pm-8:04 am

2 stops19h 14m

$357

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 1/22

5:33 am-12:40 pm

1 stop6h 07m

George Town Owen Roberts Intl

mié. 1/28

2:05 pm-9:40 am

2 stops20h 35m

$361

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 12/13

6:00 am-12:30 pm

1 stop5h 30m

George Town Owen Roberts Intl

jue. 12/18

1:50 pm-11:47 pm

1 stop10h 57m

$385

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 12/13

6:00 am-12:30 pm

1 stop5h 30m

George Town Owen Roberts Intl

mié. 12/17

1:50 pm-11:47 pm

1 stop10h 57m

$385

ChicagoGeorge Town

ORD - GCM

ORDGCM

Chicago O'Hare Intl

jue. 12/25

8:45 am-1:45 pm

Nonstop4h 00m

George Town Owen Roberts Intl

jue. 1/1

5:45 pm-12:14 am

1 stop7h 29m

$387

ChicagoGeorge Town

MDW - GCM

MDWGCM

Chicago Midway

sáb. 1/24

6:00 am-2:00 pm

1 stop7h 00m

George Town Owen Roberts Intl

sáb. 1/31

3:25 pm-10:26 pm

1 stop8h 01m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/5

Showing 1-10 of 38 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, January is the cheapest month in which you can book a flight from Chicago to Grand Cayman (average of $356). 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 noviembre 6, 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 noviembre 6, 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
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
7.9
Good
8,001 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Overall

8.0

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 35m. United Airlines provides one of the quickest options available for as low as $352. The distance between Chicago and Grand Cayman is about 1598 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 $641 for a flight from Chicago to Grand Cayman. The cheapest flight overall is $341 while the most popular route, (Chicago O'Hare Intl - George Town Owen Roberts Intl) is currently priced at $272.

  • 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 $356). 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 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 noviembre 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$434Average$721FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$488Average$707FlexibilityNo cancel feeOn-time71%
DeltaCheapest$564Average$694FlexibilityNo cancel feeOn-timeN/A

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