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Flights Chicago — George Town

Chicago
CHI
Grand Cayman
GCM

Cheap flights Chicago — George Town

Below you can see the best deals on flights Chicago — George Town for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 14 July, from AED 866.

Top 10 cheap flights Chicago — George Town

Direct flights Chicago — George Town

Direct flight options for Chicago — George Town with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by United Airlines — travel time is 4 h 4 min.

Top 10 direct flights Chicago — George Town

About the Chicago — George Town flight

On this page, you can find and buy flight tickets for the Chicago — Georgetown route. The 2,572 km flight is operated approximately 3 times a week, making it easy to find a convenient option for your trip. Before booking, we recommend checking how to get to the airport in Chicago and arranging airport transfers in Georgetown in advance.

Flights on this route are served by United Airlines and American Airlines. Ticket prices depend on the season and booking time, so use the low-price calendar and price trend chart below to find the best deal.

Flight schedule Chicago — George Town

The table shows direct flights Chicago → George Town on the selected date. The flight takes approximately 7 h. Regular flights are operated by American Airlines and United Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Owen Roberts International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

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Flight ticket prices by day: Chicago — George Town

Below is a calendar of the lowest flight ticket prices for Chicago — George Town by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 866 in y, and the most expensive are around AED 1,124 in n. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

Chicago → George Town, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 1,554highMayAED 1,189mediumSepAED 1,006low
FebAED 1,509highJunAED 1,143mediumOctAED 1,029low
MarAED 1,646highJulAED 1,509highNovAED 1,189medium
AprAED 1,463highAugAED 1,051lowDecAED 1,554high

Some values are estimated based on seasonality.

When to fly

The warmest month in Georgetown is August, when temperatures reach up to 30°C. The period from October to November is considered the rainiest: October sees up to 205 mm of precipitation, and the number of wet days can reach 21 per month.

The lowest flight price was recorded in March — AED 1,124. During the summer, ticket prices are slightly higher; for example, a flight in July will cost AED 1,183, though there is currently less data available for other months.

The best time for a trip is March, as it combines low ticket prices with dry weather. We recommend avoiding October if you want to minimize the risk of prolonged tropical downpours.

Temperature · George Town

Dry and wet days · George Town

Wind speed and direction · George Town

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How to get the best deal on a Chicago — George Town ticket

  • Use the low-price calendar to find tickets for March, when a flight costs AED 1,124 — this is the most budget-friendly time for this route.
  • Compare offers from United Airlines and American Airlines, as competition between these carriers often allows you to find lower fares on nearby dates.
  • Plan your trip in advance, keeping in mind the low flight frequency (~3 per week), to ensure you can book convenient direct flights without long layovers.
  • Check the baggage rules when booking to Georgetown, as baggage fees for economy class on international flights from the US can significantly increase the final price.

Airlines

Air service between the cities is provided by two major airlines: United Airlines and American Airlines. There are approximately 3 flights per week on this route, including both direct flights and options with layovers at major transport hubs. You can find detailed information about departure days and travel times in the interactive schedule below.

  • American AirlinesAA
    3x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → GCM3x/week
    88.9%Open →
  • United AirlinesUA
    1x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → GCM1x/week
      Duration
      4h 4m
      Days
      MTWTFSS
    11.1%Open →

Cities and airports on the Chicago — George Town route

Flights Chicago — George Town depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Owen Roberts International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

George Town

GCM
Cayman Islands
About the cityHow to get thereWeatherAll about the country Cayman Islands
Departure airports
Arrival airports

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Frequently asked questions about the Chicago — George Town flight

How long is the flight from Chicago to Georgetown?

The distance between the cities is 2,572 km. A direct flight takes approximately 3 hours and 15 minutes, although travel time may be longer if you choose a flight with a layover.

Which airlines fly this route?

Regular flights are operated by United Airlines and American Airlines. Together, these airlines offer about 3 departures per week.

Are there direct flights from Chicago to the Cayman Islands?

Yes, direct flights on this route exist, but they do not operate every day. You can check for non-stop options on specific dates in the schedule block.

How much is the cheapest ticket to Georgetown?

Prices are dynamic and depend on the season. Currently, the lowest fare is recorded in March and starts from 23,362 ₽. Look for the latest prices for your dates in the low-price calendar.

Which airport does the flight arrive at?

All flights from Chicago arrive at Owen Roberts International Airport (GCM), located directly in Georgetown.

Where else you can fly from Chicago

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Where else you can fly from George Town

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MiamiHoustonAtlantaKingstonNew York CityTorontoPanama CityFort LauderdaleTampaCayman BracCharlotteLos AngelesNassauOrlandoPhiladelphiaWashington, D.C.DenverDallasDetroitLittle CaymanMontego Bay
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