Cheap flight deals from Chicago to Grand Cayman Starting at AED 488

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

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  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Chicago to Grand Cayman?

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  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Grand Cayman (GCM) the cheapest?

    Airlines adjust prices for flights from Chicago to Grand Cayman based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Grand Cayman (GCM) cost?

    According to Trip.com's data, the lowest price is around AED 2,235.

  • How long does it take to fly from Chicago (CHI) to Grand Cayman (GCM)?

    It takes about 3 hours 51 minutes to fly from Chicago (CHI) to Grand Cayman (GCM).

  • What is the transportation method from the main airport to downtown in Grand Cayman?

    • The distance from Owen Roberts International Airport to downtown is about 11 km, by taxi about 30 minutes.

  • What are the most popular airlines that fly from Chicago (CHI) to Grand Cayman (GCM)?

    Airlines with flights from Chicago (CHI) to Grand Cayman (GCM): American Airlines and United Airlines.

  • What's the most popular airline for non-stop flights from Chicago (CHI) to Grand Cayman (GCM)?

    United Airlines operates 1 non-stop flights from Chicago (CHI) to Grand Cayman (GCM).

  • How many airports are there in Grand Cayman (GCM)?

    There are 1 airport(s) near Grand Cayman (GCM): Owen Roberts International Airport.

How to find a cheap flight from Chicago to Grand Cayman

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Grand Cayman. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Chicago to Grand Cayman ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Grand Cayman airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Tue, Apr 1 at AED 488 for one-way flights.
2
Compare cheap Chicago to Grand Cayman flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Grand Cayman. The cheapest airline operating is Frontier Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Grand Cayman route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Grand Cayman flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Grand Cayman to get exclusive deals for you.

Flight Info | Chicago to Grand Cayman

Cheapest one-way flight price AED 487
Cheapest return ticket price AED 2,134
Off-season for travel March
Peak season for travel December
Flight distance 2,580.07 km
Average flight time 3 hours 51 minutes
Popular airline American Airlines

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