$138+ Cheap flights from O'Hare Intl (ORD) 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — GCM
Jul 11 — Jul 181
Round-trip
1 adult, Economy
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Cheapest flights from O'Hare Intl to Grand CaymanExplore the most affordable flight options available from O'Hare Intl to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.
Explore the most affordable flight options available from O'Hare Intl to Grand Cayman. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 11, 2026.
This Expedia deal was found by Cheapflights users on 6/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/53:40 pm
ORD
- GCM
2 stops43h 45m
Air Canada
Sat 9/1212:25 pm
GCM
- ORD
1 stop28h 33m
Air Canada
Deal found 6/6![Air Canada logo]()
$409
This Justfly.com deal was found by Cheapflights users on 6/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/122:00 pm
ORD
- GCM
1 stop20h 00m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 6/8![Air Canada logo]()
$423
This Expedia deal was found by Cheapflights users on 6/7. 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 10/182:15 pm
ORD
- GCM
1 stop21h 15m
Air Canada
Sat 10/2412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 6/7![Air Canada logo]()
$427
This Expedia deal was found by Cheapflights users on 6/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Sat 10/2412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 6/6![Air Canada logo]()
$430
This Orbitz deal was found by Cheapflights users on 6/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/318:00 am
ORD
- GCM
1 stop28h 00m
Air Canada
Sat 11/71:10 pm
GCM
- ORD
1 stop24h 46m
Air Canada
Deal found 6/8![Air Canada logo]()
$432
This Expedia deal was found by Cheapflights users on 6/10. 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 10/228:45 am
ORD
- GCM
2 stops50h 45m
Air Canada
Mon 10/2612:10 pm
GCM
- ORD
1 stop20h 50m
Air Canada
Deal found 6/10![Air Canada logo]()
$436
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/213:40 pm
ORD
- GCM
2 stops19h 50m
Air Canada
Wed 10/2812:10 pm
GCM
- ORD
2 stops19h 45m
Air Canada
Deal found 6/7![Air Canada logo]()
$438
This Mytrip deal was found by Cheapflights users on 6/9. 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 10/1112:59 pm
ORD
- GCM
1 stop22h 31m
Air Canada
Sat 10/2412:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Deal found 6/9![Air Canada logo]()
$440
Best flights from O'Hare Intl to Grand CaymanDiscover carefully curated flight deals from O'Hare Intl to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 11, 2026.
Discover carefully curated flight deals from O'Hare Intl to Grand Cayman that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 11, 2026.
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/43:45 pm
ORD
- GCM
1 stop18h 00m
Air Canada
Mon 9/712:25 pm
GCM
- ORD
2 stops30h 21m
Air Canada
Deal found 6/9![Air Canada logo]()
$485
This Delta deal was found by Cheapflights users on 6/9. 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 10/155:30 am
ORD
- GCM
1 stop6h 10m
Delta
Fri 10/2312:55 pm
GCM
- ORD
1 stop7h 25m
Delta
Deal found 6/9![Delta logo]()
$646
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Sat 7/189:29 am
ORD
- GCM
Nonstop4h 01m
United Airlines
Sat 7/251:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Deal found 6/10![United Airlines logo]()
$667
This Air Canada deal was found by Cheapflights users on 6/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/306:30 pm
ORD
- GCM
1 stop16h 30m
Air Canada
Wed 12/21:10 pm
GCM
- ORD
1 stop26h 46m
Air Canada
Deal found 6/10![Air Canada logo]()
$491
This Delta deal was found by Cheapflights users on 6/7. 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 10/75:45 pm
ORD
- GCM
2 stops17h 55m
Delta
Sat 10/1012:55 pm
GCM
- ORD
1 stop10h 55m
Delta
Deal found 6/7![Delta logo]()
$656
This United Airlines deal was found by Cheapflights users on 6/6. 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.
Tue 7/215:30 am
ORD
- GCM
1 stop7h 00m
United Airlines
Tue 7/281:35 pm
GCM
- ORD
1 stop9h 40m
United Airlines
Deal found 6/6![United Airlines logo]()
$671
This Delta deal was found by Cheapflights users on 6/10. 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.
Sun 9/65:30 am
ORD
- GCM
1 stop6h 09m
Delta
Fri 9/1112:55 pm
GCM
- ORD
1 stop11h 02m
Delta
Deal found 6/10![Delta logo]()
$661
This Delta deal was found by Cheapflights users on 6/7. 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.
Sun 8/27:17 pm
ORD
- GCM
2 stops16h 22m
Delta
Thu 8/61:04 pm
GCM
- ORD
2 stops18h 52m
Delta
Deal found 6/7![Delta logo]()
$666
This Delta deal was found by Cheapflights users on 6/9. 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.
Sat 8/295:30 am
ORD
- GCM
1 stop6h 09m
Delta
Wed 9/21:04 pm
GCM
- ORD
1 stop10h 53m
Delta
Deal found 6/9![Delta logo]()
$671
This Delta deal was found by Cheapflights users on 6/7. 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.
Sat 8/15:30 am
ORD
- GCM
1 stop6h 01m
Delta
Thu 8/61:04 pm
GCM
- ORD
1 stop10h 53m
Delta
Deal found 6/7![Delta logo]()
$671
This Delta deal was found by Cheapflights users on 6/8. 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.
Sat 8/225:30 am
ORD
- GCM
1 stop6h 09m
Delta
Wed 8/261:04 pm
GCM
- ORD
1 stop10h 53m
Delta
Deal found 6/8![Delta logo]()
$671
Last-minute flights from O'Hare Intl to Grand CaymanDiscover last-minute flight deals from O'Hare Intl to Grand Cayman. Data last updated June 11, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Grand Cayman. Data last updated June 11, 2026 and is based on user searches.
This Justfly.com deal was found by Cheapflights users on 6/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/122:00 pm
ORD
- GCM
1 stop20h 00m
Air Canada
Mon 6/1512:25 pm
GCM
- ORD
1 stop25h 00m
Air Canada
Deal found 6/8![Air Canada logo]()
$423
This FlightHub deal was found by Cheapflights users on 6/9. 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.
Wed 6/245:35 pm
ORD
- GCM
1 stop17h 50m
Multiple Airlines
Sat 7/42:10 pm
GCM
- ORD
1 stop18h 35m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$540
This Travelocity deal was found by Cheapflights users on 6/7. 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.
Thu 7/168:45 am
ORD
- GCM
2 stops49h 15m
Air Canada
Mon 7/2012:25 pm
GCM
- ORD
1 stop28h 32m
Air Canada
Deal found 6/7![Air Canada logo]()
$574
This Travelocity deal was found by Cheapflights users on 6/6. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/229:50 am
ORD
- GCM
1 stop25h 35m
Air Canada
Mon 7/2712:25 pm
GCM
- ORD
1 stop26h 30m
Air Canada
Deal found 6/6![Air Canada logo]()
$535
This FlightHub deal was found by Cheapflights users on 6/7. 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.
Wed 7/295:35 pm
ORD
- GCM
1 stop17h 50m
Multiple Airlines
Wed 8/57:00 am
GCM
- ORD
2 stops30h 22m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$566
One-way flights from O'Hare Intl to Grand CaymanSearch for one-way flight options from O'Hare Intl to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
Search for one-way flight options from O'Hare Intl to Grand Cayman. Find affordable one-way fares based on user searches. Data last updated June 11, 2026.
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:21 pm
ORD
- GCM
2 stops17h 04m
Air Canada
Deal found 6/7![Air Canada logo]()
$138
This Travelocity deal was found by Cheapflights users on 6/9. 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.
Wed 6/171:55 pm
ORD
- GCM
2 stops21h 30m
Air Canada
Deal found 6/9![Air Canada logo]()
$143
This Expedia deal was found by Cheapflights users on 6/8. 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.
Sat 9/58:45 am
ORD
- GCM
2 stops50h 40m
Air Canada
Deal found 6/8![Air Canada logo]()
$156
This Air Canada deal was found by Cheapflights users on 6/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/12:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Deal found 6/7![Air Canada logo]()
$162
This Expedia deal was found by Cheapflights users on 6/9. 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 9/62:15 pm
ORD
- GCM
1 stop21h 10m
Air Canada
Deal found 6/9![Air Canada logo]()
$163
This Expedia deal was found by Cheapflights users on 6/11. 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.
Tue 9/88:45 am
ORD
- GCM
2 stops50h 45m
Air Canada
Deal found 6/11![Air Canada logo]()
$167
This Air Canada deal was found by Cheapflights users on 6/9. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:09 am
ORD
- GCM
1 stop28h 21m
Air Canada
Deal found 6/9![Air Canada logo]()
$168
Find flight deals from O'Hare Intl to Grand Cayman
Keep the following information in mind while searching for O'Hare Intl to Grand Cayman flight deals. Data was last updated June 11, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $409 (Expedia) |
One-way from | $138 (Air Canada) |
Popular in | December |
Cheapest in | February |
Average price | $696 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 June 11, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Grand Cayman that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Fri 9/4
3:45 pm-9:45 am
1 stop18h 00m
George Town Owen Roberts Intl
Mon 9/7
12:25 pm-6:46 pm
2 stops30h 21m
$485
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Mon 11/30
6:30 pm-12:00 pm
1 stop16h 30m
George Town Owen Roberts Intl
Wed 12/2
1:10 pm-2:56 pm
1 stop26h 46m
$491
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Thu 10/15
5:30 am-11:40 am
1 stop6h 10m
George Town Owen Roberts Intl
Fri 10/23
12:55 pm-8:20 pm
1 stop7h 25m
$646
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Wed 10/7
5:45 pm-11:40 am
2 stops17h 55m
George Town Owen Roberts Intl
Sat 10/10
12:55 pm-11:50 pm
1 stop10h 55m
$656
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 9/6
5:30 am-11:39 am
1 stop6h 09m
George Town Owen Roberts Intl
Fri 9/11
12:55 pm-11:57 pm
1 stop11h 02m
$661
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sun 8/2
7:17 pm-11:39 am
2 stops16h 22m
George Town Owen Roberts Intl
Thu 8/6
1:04 pm-7:56 am
2 stops18h 52m
$666
Quickest round-trip
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 7/18
9:29 am-1:30 pm
Nonstop4h 01m
George Town Owen Roberts Intl
Sat 7/25
1:50 pm-6:13 pm
Nonstop4h 23m
$667
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Tue 7/21
5:30 am-12:30 pm
1 stop7h 00m
George Town Owen Roberts Intl
Tue 7/28
1:35 pm-11:15 pm
1 stop9h 40m
$671
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 8/29
5:30 am-11:39 am
1 stop6h 09m
George Town Owen Roberts Intl
Wed 9/2
1:04 pm-11:57 pm
1 stop10h 53m
$671
ChicagoGeorge Town
ORD - GCM
ORDGCM
Chicago O'Hare Intl
Sat 8/1
5:30 am-11:31 am
1 stop6h 01m
George Town Owen Roberts Intl
Thu 8/6
1:04 pm-11:57 pm
1 stop10h 53m
$671
Showing 1-10 of 20 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Grand Cayman
Have a flexible travel schedule? Discover the best time to fly to Grand Cayman from O'Hare Intl with our price prediction graph.
ORD-GCM
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 O'Hare Intl Airport to Grand Cayman
ORD-zzLAW
ORD-GCM
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Grand Cayman?
Currently, December is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Grand Cayman (average of $174). Flying from Chicago O'Hare Intl Airport to Grand Cayman in September is currently the most expensive (average of $659). 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 ORD to LAW?
Find hourly flight availability from O'Hare Intl 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 June 11, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago O'Hare Intl Airport 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 June 11, 2026.
Get a feel of what it's like to fly with United Airlines and American Airlines from Chicago O'Hare Intl Airport to Grand Cayman by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Overall
7.4
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Overall
7.4
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Crew
8.1
Overall
7.4
Boarding
7.7
Food
6.6
Comfort
7.3
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Grand Cayman. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Complete your trip
Complete your trip to Grand Cayman by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Grand Cayman by cabin class
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O'Hare Intl and Grand Cayman flights
Browse other O'Hare Intl and Grand Cayman flight options. Last updated on June 11, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top 2 airlines flying from O'Hare Intl to Grand Cayman
Discover the top 2 airlines that operate flights from O'Hare Intl 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 June 11, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$341 | Average$614 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$429 | Average$675 | FlexibilityNo cancel fee | On-time71% |