The prices shown on this page were available within the last 20 days for the specified periods and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Chicago to Grand Cayman

If you’re planning to fly this route soon, keep in mind that the lowest fares are usually available at the end of December. Take advantage of this period to save on your flight tickets and make the most of your trip. Please note that prices may change after your search.

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week: 28 Dec - 3 Jan

Flights from just £195

£249

£247

£322

£290

£244

£226

£249

£522

£195

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£246

NovemberDecemberJanuary

Flight Duration7 h and 23 mFlights between Chicago and Grand Cayman take, on average, 7 h and 23 m minutes, but the time can vary according to other factors

Cheapest flight£256Cheapest price for a flight between Chicago and Grand Cayman found by our customers in the last 72 hours

Destination airportOwen Roberts International AirportFor the route from Chicago to Grand Cayman

High seasonMarchAccording to search data from our customers, March is the busiest time to fly from Chicago to Grand Cayman

Airlines flying this routeAmerican AirlinesAirline(s) with flights between Chicago to Grand Cayman

One-way average Price£301The average price for a flight Chicago - Grand Cayman at Opodo is £301, based on the price of last 6 months

Best time to bookMarchAccording to real data January is the most popular time to book a flight to Grand Cayman when departing from Chicago

Distance: 1,601 mi

Chicago airports

O'hare International Airport (ORD)How far from city centre: 13 mi

Grand Cayman airports

Book your Chicago to Grand Cayman flight

Search direct and connecting flights from Chicago to Grand Cayman (Cayman Islands) with Opodo. When your results appear, sort them by timing or fare and book whichever option fits your plans best.

The cheapest fare booked on this route in recent days was £256, although the price you're shown will vary with your travel dates and departure times.

Flying non-stop from Chicago to Grand Cayman takes roughly 5 h and 46 m, whereas journeys with a layover will take longer.

Airports and airlines on the Chicago–Grand Cayman route

Plan your trip with confidence by checking the relevant airports and comparing the airlines that fly this route.

Departure airport: O'hare International Airport (ORD)

Tips for cheaper flights from Chicago to Grand Cayman

A few ways to bring down the cost of your flight from Chicago to Grand Cayman:

Flexible dates: check fares across two or three departure days. Going a day earlier or later can make a real difference to what you pay.
Baggage allowance: see what's included in each fare before booking, so you're not stung by unexpected charges at the airport.
Airports on your route: double-check which airports you'll fly from and into, particularly if the city has more than one. It makes it easier to plan transfers and work out the full cost of getting around.

After a bigger saving? Book a Flight + Hotel package to combine the two in a single booking and unlock exclusive discounts on your stay in Grand Cayman. Adding car hire to the same booking can save you money too.

Frequently asked questions about flights from Chicago to Grand Cayman

On average, how much is the price of a flight from Chicago to Grand Cayman?

When you fly from Chicago to Grand Cayman the average price is £301. However, this price depends on many other factors such as seasonality or how far in advance the route has been booked.

How can I find cheap flights from Chicago to Grand Cayman at Opodo?

The cheapest price for a flight from Chicago to Grand Cayman is 256 £. At Opodo we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.

When is the best time to book a flight from Chicago to Grand Cayman?

The most popular months to book a flight from Chicago to Grand Cayman are January, November and February, based on the searches of our customers.

When is the best time to travel from Chicago to Grand Cayman?

The best time of the year to go to Grand Cayman when flying from Chicago depends on several preference factors like climate, seasonality and, of course, price. When it comes to popularity, February is the top 1º month to fly to Grand Cayman from Chicago in terms of searches from our customer, followed by December and March. If you prefer to avoid high peaks of turism, however, and escape a crowded period, June, May and September are the months with less volume of searchs for the route Chicago - Grand Cayman.

How long does the flight take to go from Chicago to Grand Cayman?

The total flight time between Chicago and Grand Cayman is of around 7 h and 23 m on average, considering an average distance of 1,601.36 mi, for both direct and indirect flights for the route (which may have 1 or more stops in other cities in between).

Which are the airlines with flights from Chicago to Grand Cayman?

Airlines with direct flights departing from Chicago to Grand Cayman are:

American Airlines.

Air Canada

Air Canada

Plan your trip

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