$199+ Cheap flights from Grand Cayman to O'Hare Intl (ORD)
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 4/30. Fares are subject to change and may not be available on all flights or dates of travel.
GCM — ORD
Mar 6 — Mar 131
1 adult, Economy
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Last-minute
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Cheapest flights from Grand Cayman to O'Hare IntlExplore the most affordable flight options available from Grand Cayman to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
Explore the most affordable flight options available from Grand Cayman to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Thu 3/265:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$363
This Air Canada deal was found by Cheapflights users on 2/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:10 am
GCM
- ORD
1 stop8h 15m
Air Canada
Sat 4/116:40 pm
ORD
- GCM
1 stop16h 15m
Air Canada
Deal found 2/2![Air Canada logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Multiple Airlines
Thu 3/265:01 am
ORD
- GCM
2 stops30h 34m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$414
This United Airlines deal was found by Cheapflights users on 2/1. 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 4/11:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Mon 4/68:45 am
ORD
- GCM
Nonstop4h 00m
United Airlines
Deal found 2/1![United Airlines logo]()
$491
This American Airlines deal was found by Cheapflights users on 2/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/133:35 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Wed 2/189:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Deal found 2/4![American Airlines logo]()
$495
This Orbitz deal was found by Cheapflights users on 2/2. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1812:25 pm
GCM
- ORD
1 stop20h 35m
Air Canada
Tue 7/73:40 pm
ORD
- GCM
2 stops43h 50m
Air Canada
Deal found 2/2![Air Canada logo]()
$521
This Orbitz deal was found by Cheapflights users on 2/1. 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 2/143:40 pm
GCM
- ORD
1 stop8h 41m
JetBlue
Wed 2/1810:00 am
ORD
- GCM
2 stops27h 05m
JetBlue
Deal found 2/1![JetBlue logo]()
$523
Best flights from Grand Cayman to O'Hare IntlDiscover carefully curated flight deals from Grand Cayman to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Grand Cayman to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This Air Canada deal was found by Cheapflights users on 2/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:10 am
GCM
- ORD
1 stop8h 15m
Air Canada
Sat 4/116:40 pm
ORD
- GCM
1 stop16h 15m
Air Canada
Deal found 2/2![Air Canada logo]()
$413
This Mytrip deal was found by Cheapflights users on 2/2. 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.
Thu 3/191:52 pm
GCM
- ORD
3 stops20h 28m
Spirit Airlines
Thu 3/267:17 am
ORD
- GCM
1 stop5h 40m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 2/1. 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 4/11:50 pm
GCM
- ORD
Nonstop4h 23m
United Airlines
Mon 4/68:10 pm
ORD
- GCM
1 stop16h 20m
United Airlines
Deal found 2/1![United Airlines logo]()
$491
This Orbitz deal was found by Cheapflights users on 2/1. 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 2/143:40 pm
GCM
- ORD
1 stop8h 41m
JetBlue
Wed 2/1810:00 am
ORD
- GCM
2 stops27h 05m
JetBlue
Deal found 2/1![JetBlue logo]()
$523
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/144:00 pm
GCM
- ORD
Nonstop4h 20m
American Airlines
Wed 2/189:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Deal found 2/1![American Airlines logo]()
$525
This Orbitz deal was found by Cheapflights users on 2/1. 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 2/1411:10 am
GCM
- ORD
1 stop13h 11m
Multiple Airlines
Wed 2/188:40 pm
ORD
- GCM
1 stop14h 45m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 4/111:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Mon 4/67:31 pm
ORD
- GCM
2 stops44h 34m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$570
This United Airlines deal was found by Cheapflights users on 2/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:50 pm
GCM
- ORD
Nonstop4h 14m
United Airlines
Thu 3/267:35 am
ORD
- GCM
1 stop7h 55m
United Airlines
Deal found 2/2![United Airlines logo]()
$588
Last-minute flights from Grand Cayman to O'Hare IntlDiscover last-minute flight deals from Grand Cayman to O'Hare Intl. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Grand Cayman to O'Hare Intl. Data last updated February 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/4. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/133:35 pm
GCM
- ORD
Nonstop4h 10m
American Airlines
Wed 2/189:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Deal found 2/4![American Airlines logo]()
$495
This Orbitz deal was found by Cheapflights users on 2/1. 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 2/143:40 pm
GCM
- ORD
1 stop8h 41m
JetBlue
Wed 2/1810:00 am
ORD
- GCM
2 stops27h 05m
JetBlue
Deal found 2/1![JetBlue logo]()
$523
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/144:00 pm
GCM
- ORD
Nonstop4h 20m
American Airlines
Wed 2/189:36 am
ORD
- GCM
Nonstop3h 59m
American Airlines
Deal found 2/1![American Airlines logo]()
$525
This Orbitz deal was found by Cheapflights users on 2/1. 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 2/1411:10 am
GCM
- ORD
1 stop13h 11m
Multiple Airlines
Wed 2/188:40 pm
ORD
- GCM
1 stop14h 45m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$536
This Priceline deal was found by Cheapflights users on 2/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Spirit Airlines
Thu 3/265:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$363
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 3/191:52 pm
GCM
- ORD
1 stop9h 25m
Multiple Airlines
Thu 3/265:01 am
ORD
- GCM
2 stops30h 34m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$414
One-way flights from Grand Cayman to O'Hare IntlSearch for one-way flight options from Grand Cayman to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Grand Cayman to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Expedia deal was found by Cheapflights users on 2/3. 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 4/301:40 pm
GCM
- ORD
1 stop10h 01m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:49 pm
GCM
- ORD
1 stop9h 16m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$201
This Trip.com deal was found by Cheapflights users on 2/2. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:15 pm
GCM
- ORD
1 stop9h 32m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 2/3. 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.
Thu 4/301:40 pm
GCM
- ORD
1 stop7h 37m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Thu 2/262:49 pm
GCM
- ORD
2 stops34h 51m
Spirit Airlines
Deal found 2/2![Spirit Airlines logo]()
$223
This Priceline deal was found by Cheapflights users on 2/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:40 pm
GCM
- ORD
1 stop10h 01m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$224
This Mytrip deal was found by Cheapflights users on 2/3. 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 3/2411:30 am
GCM
- ORD
1 stop7h 01m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Sun 3/12:49 pm
GCM
- ORD
2 stops27h 34m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$240
This Gotogate deal was found by Cheapflights users on 2/3. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/91:30 pm
GCM
- ORD
1 stop9h 35m
Air Canada
Deal found 2/3![Air Canada logo]()
$247
Find flight deals from Grand Cayman to O'Hare Intl
Keep the following information in mind while searching for Grand Cayman to O'Hare Intl flight deals. Data was last updated February 4, 2026.
Round-trip from | $363 (Priceline) |
|---|---|
One-way from | $199 (Expedia) |
Popular in | March |
Cheapest in | February |
Average price | $454 |
Cheapflights Fare Finder
Customize your flight search to find flights from Grand Cayman to O'Hare Intl 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 February 4, 2026.
Use the filters below to find and compare flights from Grand Cayman to Chicago O'Hare Intl Airport that are best for you.
Fly from
Grand Cayman
Fly to
O'Hare Intl
Route
Depart
Return
Price
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Fri 4/10
11:10 am-7:25 pm
1 stop8h 15m
Chicago O'Hare Intl
Sat 4/11
6:40 pm-10:55 am
1 stop16h 15m
$413
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 3/19
1:52 pm-10:20 am
3 stops20h 28m
Chicago O'Hare Intl
Thu 3/26
7:17 am-12:57 pm
1 stop5h 40m
$469
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Wed 4/1
1:50 pm-6:13 pm
Nonstop4h 23m
Chicago O'Hare Intl
Mon 4/6
8:10 pm-12:30 pm
1 stop16h 20m
$491
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Sat 2/14
3:40 pm-11:21 pm
1 stop8h 41m
Chicago O'Hare Intl
Wed 2/18
10:00 am-2:05 pm
2 stops27h 05m
$523
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Sat 2/14
4:00 pm-7:20 pm
Nonstop4h 20m
Chicago O'Hare Intl
Wed 2/18
9:36 am-2:35 pm
Nonstop3h 59m
$525
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Sat 2/14
11:10 am-11:21 pm
1 stop13h 11m
Chicago O'Hare Intl
Wed 2/18
8:40 pm-12:25 pm
1 stop14h 45m
$536
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Wed 4/1
11:30 am-6:31 pm
1 stop7h 01m
Chicago O'Hare Intl
Mon 4/6
7:31 pm-4:05 pm
2 stops44h 34m
$570
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 3/19
1:50 pm-6:04 pm
Nonstop4h 14m
Chicago O'Hare Intl
Thu 3/26
7:35 am-3:30 pm
1 stop7h 55m
$588
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 2/26
2:49 pm-11:05 pm
1 stop9h 16m
$201
George TownChicago
GCM - ORD
GCMORD
George Town Owen Roberts Intl
Thu 2/26
2:49 pm-12:40 am
2 stops34h 51m
$223
Showing 1-10 of 18 results
Best time to book a flight from Grand Cayman to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Grand Cayman with our price prediction graph.
GCM-ORD
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 Grand Cayman to Chicago O'Hare Intl Airport
zzLAW-ORD
GCM-ORD
What is the cheapest time of day to fly from LAW to ORD?
Find hourly flight availability from Grand Cayman to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 4, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Grand Cayman to Chicago O'Hare Intl Airport as you normally would.
Related info for your journey
Find useful and relevant information for your journey from Grand Cayman to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsSchaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora
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