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Find the best flight from Chicago to Grand Cayman

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Great deals to Grand Cayman
We’ve searched 100s of deals recently found by travelers.*
Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Thu, 12/6 - Tue, 12/18
JetBlue - 1 Stop, Roundtrip, Economy
$397
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Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Sat, 9/22 - Fri, 9/28
American Airlines - 1 Stop, Roundtrip, Economy
$400
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Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Fri, 9/14 - Tue, 9/18
American Airlines - 1 Stop, Roundtrip, Economy
$402
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Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Sat, 9/15 - Tue, 9/18
American Airlines - 1 Stop, Roundtrip, Economy
$403
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Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Sat, 9/8 - Sat, 9/15
American Airlines - 2 Stops, Roundtrip, Economy
$405
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Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Mon, 11/26 - Fri, 11/30
JetBlue - 1 Stop, Roundtrip, Economy
$407
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Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Thu, 9/13 - Fri, 9/21
JetBlue - 1 Stop, Roundtrip, Economy
$485
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Washington DC, DC (WAS) Grand Cayman, KY (GCM)
Thu, 9/6 - Mon, 9/10
American Airlines - 1 Stop, Roundtrip, Economy
$528
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*Prices are based on round trip travel with returns between 1-21 days after departure. These are the best fares found by travelers who searched TripAdvisor and a select group of our fare search partners in the past 72 hours. Ticket prices and seat availability change rapidly and cannot be guaranteed.
Hotels with great views in Grand Cayman
Caribbean Club Luxury Boutique Hotel
Caribbean Club Luxury Boutique Hotel
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Compass Point Dive Resort
Compass Point Dive Resort
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Christopher Columbus Condos
Christopher Columbus Condos
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Coral Stone Club
Coral Stone Club
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Route information
  • Chicago, IL is 1,616 miles from Grand Cayman
  • There are 2 weekly flights from Chicago, IL to Grand Cayman
  • 1 non-stop flights are operating from Chicago, IL to Grand Cayman today
  • United Airlines has the most nonstop flights between Chicago, IL and Grand Cayman
  • Miami, FL - Miami International Airport is the most popular connection for one stop flights between Chicago, IL and Grand Cayman
In-Flight information
  • The average flying time for a direct flight from Chicago, IL to Grand Cayman is 3 hours 57 minutes
  • Most direct flights leave around 13:05 CDT
  • Cayman Airways flight #505 is today's earliest flight from Chicago, IL to Grand Cayman (13:05 CDT, Boeing 737-300 pax)
  • Cayman Airways flight #505 is today's latest flight from Chicago, IL to Grand Cayman (13:05 CDT, Boeing 737-300 pax)
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Arrival information
  • Grand Cayman is 7 mi from Owen Roberts Intl Airport (Grand Cayman).
  • Owen Roberts Intl Airport (Grand Cayman)
    • Right now, 9 airlines operate out of Owen Roberts Intl Airport.
    • Owen Roberts Intl Airport offers nonstop flights to 19 cities.
    • Every week, at least 46 domestic flights and 77 international flights depart from Owen Roberts Intl Airport.
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