Cheap flights from the Cayman Islands to Chicago from $235
This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from the Cayman Islands to Chicago departing on 12/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Not ready to book? to track prices.Air Canada flights from Cayman Islands to Chicago O'Hare Intl Airport
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United Airlines flights from Cayman Islands to Chicago O'Hare Intl Airport
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Use the filters below to find and compare flights from the Cayman Islands to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 10/31
12:10 pm-4:38 pm
1 stop28h 28m
Chicago O'Hare Intl
Mon 11/30
8:45 am-12:10 pm
1 stop26h 25m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 10/31
12:10 pm-7:58 pm
1 stop7h 48m
Chicago O'Hare Intl
Mon 11/30
1:55 pm-12:10 pm
2 stops21h 15m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sun 11/8
1:10 pm-5:43 pm
1 stop29h 33m
Chicago O'Hare Intl
Tue 11/10
10:15 am-12:10 pm
1 stop24h 55m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Fri 12/4
1:10 pm-9:08 am
1 stop20h 58m
Chicago O'Hare Intl
Mon 12/7
8:40 pm-12:10 pm
1 stop14h 30m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Fri 12/4
1:10 pm-7:58 pm
1 stop7h 48m
Chicago O'Hare Intl
Mon 12/7
3:45 pm-12:10 pm
2 stops19h 25m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 11/21
1:10 pm-9:23 am
1 stop21h 13m
Chicago O'Hare Intl
Sat 11/28
4:40 pm-12:10 pm
1 stop18h 30m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Sat 11/21
1:10 pm-7:58 pm
1 stop7h 48m
Chicago O'Hare Intl
Sat 11/28
1:55 pm-12:10 pm
2 stops21h 15m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Fri 12/4
1:10 pm-8:00 am
2 stops19h 50m
Chicago O'Hare Intl
Mon 12/7
1:55 pm-12:10 pm
2 stops21h 15m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Wed 2/24
3:11 pm-6:51 pm
Nonstop4h 40m
Chicago O'Hare Intl
Sun 3/7
9:10 am-2:12 pm
Nonstop4h 02m
George TownChicago
GCM George Town Owen Roberts Intl - ORD Chicago O'Hare Intl
GCMORD
George Town Owen Roberts Intl
Mon 12/28
5:45 pm-9:25 pm
Nonstop4h 40m
Chicago O'Hare Intl
Sat 1/2
10:40 am-3:47 pm
Nonstop4h 07m
See travel insights to Chicago from
How to get the cheapest flight ticket from Cayman Islands to Chicago O'Hare Intl Airport
Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip
What is the cheapest month to fly to Chicago O'Hare Intl Airport?
The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Cayman Islands averaging around $0.
What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?
The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Saturday when prices can be found for as low as $571. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Cayman Islands because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $1,941.
What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?
Flying to Chicago O'Hare Intl Airport from Cayman Islands at noon is the least expensive time of day to depart. momondo users have found prices as low as $600 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $666. Of course, these prices can vary depending on the time of year and what airport you fly to.
What is the cheapest Cayman Islands to Chicago O'Hare Intl flight route?
Fly from George Town Owen Roberts Intl to Chicago O'Hare Intl for the best Cayman Islands - Chicago O'Hare Intl flight prices
What cabin class options are available on Cayman Islands to Chicago O'Hare Intl Airport flights?
There are 2 cabin classes available to choose from on Cayman Islands to Chicago O'Hare Intl Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.
Can stopping save me money on Cayman Islands to Chicago O'Hare Intl Airport flights?
No. A direct flight is the cheapest option for a flight between Cayman Islands to Chicago O'Hare Intl Airport.
Cheap Cayman Islands to Chicago O'Hare Intl Airport flight deals and tips
Find info about flight duration, direct flights, and airports for your flight from Cayman Islands to Chicago O'Hare Intl Airport
Frequently asked questions about flying from the Cayman Islands to Chicago O'Hare Intl Airport
When did momondo last update prices for flights from Cayman Islands to Chicago O'Hare Intl Airport?
Prices for flights from Cayman Islands to Chicago O'Hare Intl Airport are updated daily.
How many operators does momondo search for flights from Cayman Islands to Chicago O'Hare Intl Airport?
There is 1 operator available for flights from Cayman Islands to Chicago O'Hare Intl Airport as of October 2026.
How old do you have to be to fly from Cayman Islands to Chicago O'Hare Intl Airport?
The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cayman Islands to Chicago O'Hare Intl Airport.
What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?
The necessary travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.
What is the most popular plane model from Cayman Islands to Chicago O'Hare Intl Airport?
Based on momondo bookings for flights between Cayman Islands and Chicago O'Hare Intl Airport, the leading plane model is Boeing 737 MAX 8, making up 39.29% of the total bookings. Other popular models include Boeing 737-800 with 39.29%, Boeing 737-800 Passenger/BBJ2 (winglets) with 10.71%, and Boeing 737 MAX 9 with 3.57%.
Best airlines flying from Cayman Islands to Chicago O'Hare Intl Airport
Compare and see reviews for airlines that fly from Cayman Islands to Chicago O'Hare Intl Airport with momondo
| Airline | Rating | Free Cancellation | Price | ||
|---|---|---|---|---|---|
| PriceFrom $571 | Free Cancellation | Rating 7.0 12,145 reviews |
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Why should I use momondo to find a flight deal from Cayman Islands to Chicago?
It is quick and easy to find Cayman Islands to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.
Can I find flights from Cayman Islands to Chicago with flexible booking policies on momondo?
Flights from Cayman Islands to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.
How can momondo help me find flights from Cayman Islands to Chicago?
momondo provides multiple filters to help you find the best flight to Chicago from Cayman Islands. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.
I’m not ready to book a flight from Cayman Islands to Chicago right now. Can momondo alert me if prices change?
Yes momondo offers price alerts on flights to Chicago from Cayman Islands. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.