Flights from Chicago to Grand Cayman Starting at NZD 232

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

  • Round-trip
  • One way

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

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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.

Airlines Flying from Chicago to Grand Cayman

Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Cayman Airways logo Cayman Airways

FAQ

  • 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 departure date and time of your selection. By analyzing data from all airlines, we've discovered that 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 NZD 1,062.

  • How long does it take to fly from Chicago (CHI) to Grand Cayman (GCM) and what is the distance?

    It takes around 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. It takes about 30 minutes by taxi.

  • 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.

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
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
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4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
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Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Information from Chicago to Grand Cayman

Cheapest one-way flight price NZD 231
Cheapest round-trip ticket price NZD 1,014
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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