Chicago, IL, USA to Grand Cayman from $205: 4 ways by bus, train, flight or car

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How to Get from Chicago to Grand Cayman: Cheapest, Fastest and Best Way

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$205 - PlaneBest price

2594 kmDistance

6h 23m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Chicago to Grand Cayman with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

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Traveling From Chicago to Grand Cayman

Travelers will find a striking contrast between the bustling city life of Chicago, with its vibrant urban culture, and the serene beaches and laid-back atmosphere of Grand Cayman.

Best Neighbourhoods in Grand Cayman

Grand Cayman boasts diverse neighborhoods, each offering unique experiences to visitors.

Seven Mile Beach

• Stunning white-sand beaches stretch for miles.

• Home to upscale resorts and dining options.

George Town

• The heart of the island’s shopping and culture.

• Bustling cruise port with lively waterfront.

West Bay

• Tranquil beaches and family-friendly attractions.

• Ideal for snorkeling and diving adventures.

Best Times To Visit Grand Cayman's Attractions

Visiting Grand Cayman is a delight, especially when you choose the right times for major attractions.

Stingray City

Early morning visits offer a quieter experience with fewer tourists.

Seven Mile Beach

Late afternoon is perfect for stunning sunsets and smaller crowds.

The Cayman Islands National Museum

Weekdays are ideal for exploring without the weekend rush.

Grand Cayman Weather: What to Expect Year-Round

Grand Cayman boasts a tropical climate characterized by warm temperatures and occasional rain, creating ideal conditions year-round. The best times to visit are during the winter months when humidity is lower, ensuring that pleasant weather enhances your island experience.

Dining in Grand Cayman

Try the fresh conch fritters at The Fish Shack, where the relaxed island vibe and ocean views offer a stark contrast to Chicago's bustling culinary scene. This dish showcases local ingredients and flavors, providing a taste of the Caribbean that’s both vibrant and refreshing.

Chicago - Grand Cayman operators

Explore transport companies operating between Chicago and Grand Cayman, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane

Website

aa.com

Plane from Chicago O'Hare (ORD) to Grand Cayman (GCM)

Average Duration

3h 50m

Estimated price

$2585-2586

Plane from Chicago O'Hare (ORD) to Grand Cayman (GCM) via Miami

Average Duration

Estimated price

$2585-2586

Plane from Chicago O'Hare (ORD) to Grand Cayman (GCM) via Charlotte

Average Duration

6h 19m

Estimated price

$2585-2586

Website

delta.com

Plane from Chicago O'Hare (ORD) to Grand Cayman (GCM) via Atlanta

Average Duration

7h 5m

Estimated price

$258360-6241

Plane from Chicago Midway (MDW) to Grand Cayman (GCM) via Atlanta

Average Duration

5h 42m

Estimated price

$6242-2589

Plane from South Bend (SBN) to Grand Cayman (GCM) via Atlanta

Average Duration

6h 20m

Estimated price

$6243-2588

Plane from South Bend (SBN) to Grand Cayman (GCM) via Minneapolis

Average Duration

7h 24m

Estimated price

$6244-6245

Website

united.com

Plane from Chicago O'Hare (ORD) to Grand Cayman (GCM)

Average Duration

Estimated price

$258300-6246

Plane from South Bend (SBN) to Grand Cayman (GCM) via Chicago O'Hare

Average Duration

7h 35m

Estimated price

$258380-2587

Plane from Milwaukee (MKE) to Grand Cayman (GCM) via Chicago O'Hare

Average Duration

6h 52m

Estimated price

$258320-6247

Website

southwest.com

Plane from Chicago Midway (MDW) to Grand Cayman (GCM) via Orlando

Average Duration

5h 20m

Estimated price

$258370-6248

Plane from Chicago Midway (MDW) to Grand Cayman (GCM) via Fort Lauderdale-Hollywood International

Average Duration

6h 15m

Estimated price

$258370-6248

Plane from Milwaukee (MKE) to Grand Cayman (GCM) via Orlando

Average Duration

7h 10m

Estimated price

$258340-2581

Website

caymanairways.com

Plane from Chicago Midway (MDW) to Grand Cayman (GCM) via Tampa

Average Duration

5h 10m

Estimated price

$258370-6248

Plane from Chicago Midway (MDW) to Grand Cayman (GCM) via Miami

Average Duration

5h 47m

Estimated price

$258370-6248

Train

Contact phone

+1 219-926-5744

Website

mysouthshoreline.com

Train from Van Buren St. to South Bend Airport

Average Duration

2h 35m

Estimated price

$6249-2880

Contact phone

+1 800-872-7245

Website

amtrak.com

Train from Chicago Union Station to Milwaukee

Average Duration

1h 29m

Estimated price

$2883-28815

Chicago to Grand Cayman: Overview of Bus, Train, Flight, and Car Trips

Traveling between Chicago and Grand Cayman offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🛫 Traveling from Chicago to Grand Cayman by plane is a convenient and efficient journey. The quickest direct flight from Chicago O'Hare Airport to Grand Cayman Airport only takes 3 hours and 50 minutes. 🌴 With airlines such as United Airlines, Delta, and American Airlines offering flights between the two locations, travelers have a variety of options to choose from for their trip. The total duration of the flight from Chicago to Grand Cayman typically averages around 6 hours and 40 minutes. 💸 When it comes to pricing, flights from Grand Cayman to Chicago can range from $258 to $624, providing travelers with a range of choices to fit their budget and travel preferences. Overall, the trip offers a seamless and relatively quick way to reach the stunning destination of Grand Cayman from the bustling city of Chicago.

Departure Point

Chicago O'Hare Airport

Arrival Point

Grand Cayman Airport

Frequently asked questions

Find out more about the route from Chicago to Grand Cayman.

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The cheapest way to get from Chicago to Grand Cayman is by flying. The average cost of a round trip ticket ranges from $140 to $440, depending on the time of year and availability. The flight duration typically takes around 8 hours and 14 minutes. It is recommended to book in advance and compare prices from different airlines to find the best deal.

The fastest way to travel from Chicago to Grand Cayman is by taking a direct flight. The flight duration is approximately 6 hours and 37 minutes. There are several airlines that operate direct flights between these two destinations, offering convenient and efficient travel options. Prices for these flights can range from $250 to $550, depending on the airline and time of booking.

The distance from Chicago to Grand Cayman is approximately 1612 miles. This distance is based on a straight line or the shortest distance between the two locations. Keep in mind that when traveling by air, the actual distance might be longer due to the flight route. It's important to check with airlines or travel agencies for the most accurate information regarding flight distances and durations.

The travel time from Chicago to Grand Cayman is approximately 6 hours and 37 minutes, including transfers. This duration may vary depending on factors such as layovers and flight schedules. It is advisable to check with airlines for the most accurate and up-to-date information regarding travel times for your specific travel dates.

There are plenty of accommodation options available near Grand Cayman, with over 222 hotels to choose from. Prices for hotels in Grand Cayman start at $255 per night. Some popular areas to stay in Grand Cayman include Seven Mile Beach, Georgetown, and West Bay. It is recommended to book your accommodation in advance, especially during peak travel seasons, to secure the best deals and availability.

To get to Grand Cayman from the airport, you will need to take a flight. Upon arrival at Owen Roberts International Airport in Grand Cayman, you can take a taxi or arrange for airport transfer services to your destination. Taxis are readily available and can take you directly to your hotel or desired location on the island. Alternatively, you can rent a car if you prefer to have the flexibility to explore the island at your own pace.

Delta, United Airlines, and American Airlines offer flights from Chicago to Grand Cayman. These airlines provide direct flights from Chicago O'Hare Airport to Grand Cayman Airport. Passengers can choose from multiple flights each day to find the most convenient and suitable option for their travel plans. It is advisable to check the airlines' websites or consult a travel agent to find the most up-to-date flight schedules and ticket prices.

The fastest way to travel from Chicago to Grand Cayman is by taking a direct flight. The flight duration from Chicago O'Hare Airport to Grand Cayman Airport is approximately 3 hours and 47 minutes. Airlines such as Delta, United Airlines, and American Airlines operate flights between these two destinations. The flight duration for a one-way trip is approximately 6 hours and 37 minutes. Prices for flights range from $258 to $514.

The flight duration from Chicago to Grand Cayman is approximately 3 hours and 47 minutes on the quickest direct flight. However, this may vary depending on factors such as winds and air traffic. It's always a good idea to check with the airline for the most accurate and up-to-date flight times.

The cost of a flight from Chicago to Grand Cayman can range from $258 to $514. The price of the flight depends on various factors such as the date of travel, the airline chosen, and the availability of tickets. It is recommended to book your flight well in advance and compare different airlines to find the best deals.