$262 Find Cheap Flights from Cayman Islands to Chicago O'Hare Airport - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to O'Hare Intl departing on 9/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from the Cayman Islands to O'Hare Intl

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from the Cayman Islands to O'Hare Intl that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from the Cayman Islands to O'Hare Intl

Fri, Oct 9 - Wed, Oct 14
Multiple Airlines Logo
7:00 am - 9:00 am
GCM
-
ORD
26h 00m
2 stops
Multiple Airlines Logo
8:40 pm - 11:30 am
ORD
-
GCM
14h 50m
1 stop
$505Multiple Airlines
Fri, Oct 9 - Wed, Oct 14
Multiple Airlines Logo
7:00 am - 4:58 pm
GCM
-
ORD
33h 58m
2 stops
Multiple Airlines Logo
3:40 pm - 11:30 am
ORD
-
GCM
19h 50m
2 stops
$509Multiple Airlines
Thu, Oct 8 - Tue, Oct 13
American Airlines Logo
12:40 pm - 9:26 pm
GCM
-
ORD
8h 46m
1 stop
American Airlines Logo
5:22 am - 11:00 am
ORD
-
GCM
5h 38m
1 stop
$525American Airlines
Thu, Oct 8 - Tue, Oct 13
American Airlines Logo
3:30 pm - 11:53 pm
GCM
-
ORD
8h 23m
2 stops
American Airlines Logo
5:22 am - 11:00 am
ORD
-
GCM
5h 38m
1 stop
$530American Airlines
Thu, Oct 8 - Mon, Oct 12
Multiple Airlines Logo
12:25 pm - 2:55 pm
GCM
-
ORD
26h 30m
1 stop
Multiple Airlines Logo
8:40 pm - 10:25 am
ORD
-
GCM
37h 45m
2 stops
$579Multiple Airlines
Thu, Oct 8 - Tue, Oct 13
Air Canada Logo
12:25 pm - 7:44 am
GCM
-
ORD
43h 19m
2 stops
Air Canada Logo
2:01 pm - 11:30 am
ORD
-
GCM
45h 29m
2 stops
$587Air Canada
Fri, Nov 6 - Mon, Nov 9
United Airlines Logo
5:45 pm - 9:11 pm
GCM
-
ORD
28h 26m
1 stop
United Airlines Logo
2:15 pm - 4:30 pm
ORD
-
GCM
25h 15m
1 stop
$602United Airlines
Thu, Oct 8 - Mon, Oct 12
Multiple Airlines Logo
12:25 pm - 7:44 am
GCM
-
ORD
43h 19m
2 stops
Multiple Airlines Logo
8:40 pm - 10:25 am
ORD
-
GCM
37h 45m
2 stops
$608Multiple Airlines
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
12:40 pm - 7:11 pm
GCM
-
ORD
6h 31m
1 stop
American Airlines Logo
5:22 am - 11:00 am
ORD
-
GCM
5h 38m
1 stop
$611American Airlines
Thu, Oct 8 - Mon, Oct 12
American Airlines Logo
3:30 pm - 11:53 pm
GCM
-
ORD
8h 23m
2 stops
American Airlines Logo
8:34 pm - 11:00 am
ORD
-
GCM
14h 26m
1 stop
$616American Airlines
Booking Insights

KAYAK's insights & trends for flights to O'Hare Intl

Get data-powered insights and trends for flights to O'Hare Intl to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest day to fly to Chicago?

The average price of all round-trip flights to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.

Based on KAYAK data, the cheapest day to fly to Chicago is Sunday where round-trip tickets can be as cheap as $381. On the other hand, the most expensive day to fly is Friday, where round-trip prices are $2,559 on average.

What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

The average price for all round-trip flights to Chicago O'Hare Intl Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the afternoon, when round-trip flights cost $513 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $707.

Good to know

Low seasonNovember
Cheapest flight$262
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 77% increase in price.
Flight from George Town to Chicago

FAQs - booking Chicago O'Hare Airport flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The city center of Chicago is 16 miles from Chicago O'Hare Intl Airport.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $329. The cheapest price found on KAYAK in the last 2 weeks cost $196 and departed from George Town Owen Roberts Intl Airport.

  • How does KAYAK find such low prices on flights to Chicago O'Hare Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago O'Hare Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago O'Hare Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago O'Hare Airport is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights to Chicago O'Hare Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago O'Hare Airport with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago O'Hare Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago O'Hare Airport up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Chicago O'Hare Airport

  • Looking for cheap airfare to Chicago O'Hare Airport? 25% of our users found round-trip tickets to Chicago O'Hare Airport for the following prices or less: From George Town $263
  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago O'Hare Airport flight deals.

Reviews of the top airline flying from the Cayman Islands to O'Hare Intl

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from the Cayman Islands to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to O'Hare Intl? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 11666 reviews
7.5Boarding
6.8Entertainment
7.9Crew
6.4Food
7.2Comfort
Airline reviews

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

6.0 GoodJeffrey, Jun 2026
BOS - ORD
Read more American Airlines reviews

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight from LA to Chicago was smooth and service was very good overall.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

They lost my baggage and I am still struggling to the information and update

The homeless eat better than what was served on that plane. Pretzels and ice cream? My last trip to Europe. Everything is small, but the bill.

Awful customer service, horrible experience. We travel a lot domestic & international- worst flights to/from ever. Brief bkgd as Inhate to relive this experience: booked and chose 2 seats 4 months prior in Premium Economy - last row end seats close to bathroom, no one behind us, plenty of legroom;, underwear storage — flown this was on other airlines, love it. We receive notice 4 days before scheduled overseas flight - plane has changed, new seats assigned. Seats are split into single seats, opposites of the plane, FRONT Row so no reachable storage. Called BOTH British Air & America. American “switched planes and the seats you want are taken;” British Air “Yes, we’ll be glad to accommodate you (type type type). Just ask at the Gate and someone will give you new boarding passes with seats together in middle, OK?” — OK. —At Gate the attendant looks us up saying “No, it is an overbooked flight and yours are the only seats available.” But but but wait, “We were TOLD our seats had been switched and seated together?” Gate attendant “Well they were wrong and don’t change your seats. Your original seats are where you’ll sit.”. Right. No help WHATSOEVER. We sit opposite on way there, wife VERY disgruntled, a Tol 5 worst ways to start a 3-week bus tour of UK. We promise to NEVER FLY AMERICAN OR BROTISH AIR EVER, and we have 3 more extensive trips planned..

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Traveling to a place near O'Hare Intl?

Book flights to O'Hare Intl if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Hammond
Elk Grove Village
Des Plaines
Hoffman Estates
Portage
Willowbrook
South Holland
Delavan
Lansing
Northbrook
Lisle
Elmhurst
Pleasant Prairie
Alsip

Everything you need to know for your flight to O'Hare Intl

Information on the airport you'll fly into in Chicago