Cheap Flights from Chicago to Little Cayman
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Flights from Chicago to Little Cayman Starting at NZD 800
We've found these cheap flights for you. You can book one-way or return flight tickets.
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Round-trip
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One way
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MDW 18:4536h 55m2 stopsLYB 07:40Chicago - Little Cayman | Sat, Apr 26 | Southwest Airlines
LYB 17:3539h 35m2 stopsMDW 09:10Little Cayman - Chicago | Sat, May 3 | Cayman AirwaysNZD 1,337 NZD 1,93531% OFF31% OFFNZD 1,935 NZD 1,337 -
ORD 16:0025h 35m2 stopsLYB 17:35Chicago - Little Cayman | Sat, Apr 19 | Air Canada
LYB 17:3549h 55m2 stopsORD 19:30Little Cayman - Chicago | Sat, Apr 26 | Cayman AirwaysNZD 1,440 NZD 1,93526% OFF26% OFFNZD 1,935 NZD 1,440 -
ORD 18:2537h 15m2 stopsLYB 07:40Chicago - Little Cayman | Sat, Apr 26 | United Airlines
LYB 17:3525h 8m2 stopsORD 18:43Little Cayman - Chicago | Sat, May 3 | Cayman AirwaysNZD 1,471 NZD 1,93524% OFF24% OFFNZD 1,935 NZD 1,471 -
ORD 20:1518h 50m2 stopsLYB 15:05Chicago - Little Cayman | Tue, Apr 22 | United Airlines
LYB 08:5014h 50m2 stopsORD 23:40Little Cayman - Chicago | Tue, Apr 29 | Cayman AirwaysNZD 1,52421% OFFNZD 1,935 NZD 1,524
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ORD 19:5521h 50m2 stopsLYB 17:45Chicago - Little Cayman | Thu, Apr 17 | United Airlines
LYB 16:0031h 13m2 stopsORD 23:13Little Cayman - Chicago | Sun, Apr 20 | Cayman AirwaysNZD 1,53920% OFFNZD 1,935 NZD 1,539
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ORD 05:1512h 30m2 stopsLYB 17:45Chicago - Little Cayman | Fri, Apr 18 | United Airlines
LYB 08:5024h 35m2 stopsORD 09:25Little Cayman - Chicago | Fri, Apr 25 | Cayman AirwaysNZD 1,54720% OFFNZD 1,935 NZD 1,547
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ORD 21:4017h 25m2 stopsLYB 15:05Chicago - Little Cayman | Sun, Mar 16 | United Airlines
LYB 16:0026h 6m1 stopsORD 18:06Little Cayman - Chicago | Sun, Mar 23 | Cayman AirwaysNZD 1,54920% OFFNZD 1,935 NZD 1,549
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ORD 21:5019h 55m2 stopsLYB 17:45Chicago - Little Cayman | Thu, Apr 24 | United Airlines
LYB 08:5014h 50m2 stopsORD 23:40Little Cayman - Chicago | Mon, Apr 28 | Cayman AirwaysNZD 1,55819% OFFNZD 1,935 NZD 1,558
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ORD 05:1512h 10m2 stopsLYB 17:25Chicago - Little Cayman | Sat, Apr 19 | United Airlines
LYB 17:3524h 32m1 stopsORD 18:07Little Cayman - Chicago | Sat, Apr 26 | Cayman AirwaysNZD 1,60017% OFFNZD 1,935 NZD 1,600
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ORD 06:3011h 15m2 stopsLYB 17:45Chicago - Little Cayman | Sat, Mar 29 | United Airlines
LYB 14:1017h 25m2 stopsORD 07:35Little Cayman - Chicago | Sat, Apr 5 | Cayman AirwaysNZD 1,7619% OFFNZD 1,935 NZD 1,761
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CHI 13:0017h 25m1 stopsLYB Invalid DateChicago - Little Cayman | Tue, Mar 18 | Normal Airline
LYB 15:006hNonstopCHI 16:00Little Cayman - Chicago | Thu, Mar 20 | Normal AirlineFind More FlightsFind More Flights
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ORD 21:4536h 40m2 stopsLYB 10:25Chicago - Little Cayman | Mon, Apr 21 | United AirlinesNZD 800 NZD 1,23435% OFF35% OFFNZD 1,234 NZD 800
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ORD 21:4020h 5m2 stopsLYB 17:45Chicago - Little Cayman | Fri, Mar 21 | United AirlinesNZD 937 NZD 1,23424% OFF24% OFFNZD 1,234 NZD 937
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ORD 14:5026h 55m2 stopsLYB 17:45Chicago - Little Cayman | Fri, Mar 21 | American AirlinesNZD 1,123 NZD 1,2349% OFF9% OFFNZD 1,234 NZD 1,123 -
CHI 13:0017h 25m1 stopsLYB Invalid DateChicago - Little Cayman | Tue, Mar 18 | Normal AirlineFind More FlightsFind More Flights
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FAQ
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When are flight tickets from Chicago (CHI) to Little Cayman (LYB) the cheapest?
Airlines adjust prices for flights from Chicago to Little 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 Little Cayman (LYB) cost?
According to Trip.com's data, the lowest price is around NZD 1,555.
How to find a cheap flight from Chicago to Little Cayman
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Flight Information from Chicago to Little Cayman
| Off-season for travel | April |
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| Peak season for travel | March |
| Flight distance | 2,570.08 km |
| Popular airline | United Airlines |