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Flights from Chicago to Little Cayman
Cheap flight deals from Chicago to Little Cayman Starting at AED 1,679
We've found these cheap flights for you. You can book one-way or round-trip 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 AirlinesLYB 17:3539h 35m2 stopsMDW 09:10Little Cayman - Chicago | Sat, May 3 | Cayman AirwaysAED 2,822 AED 3,71024% OFF24% OFFAED 3,710 AED 2,822
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ORD 16:0025h 35m2 stopsLYB 17:35Chicago - Little Cayman | Sat, Apr 19 | Air CanadaLYB 17:3549h 55m2 stopsORD 19:30Little Cayman - Chicago | Sat, Apr 26 | Cayman AirwaysAED 3,040 AED 3,71018% OFF18% OFFAED 3,710 AED 3,040
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ORD 18:2537h 15m2 stopsLYB 07:40Chicago - Little Cayman | Sat, Apr 26 | United AirlinesLYB 17:3525h 8m2 stopsORD 18:43Little Cayman - Chicago | Sat, May 3 | Cayman AirwaysAED 3,104 AED 3,71016% OFF16% OFFAED 3,710 AED 3,104
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ORD 20:1518h 50m2 stopsLYB 15:05Chicago - Little Cayman | Tue, Apr 22 | United AirlinesLYB 08:5014h 50m2 stopsORD 23:40Little Cayman - Chicago | Tue, Apr 29 | Cayman AirwaysAED 3,21613% OFFAED 3,710 AED 3,216
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ORD 21:4517h 20m2 stopsLYB 15:05Chicago - Little Cayman | Mon, Apr 28 | United AirlinesLYB 08:5012h 40m2 stopsORD 21:30Little Cayman - Chicago | Mon, May 5 | Cayman AirwaysAED 3,22413% OFFAED 3,710 AED 3,224
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ORD 19:5521h 50m2 stopsLYB 17:45Chicago - Little Cayman | Thu, Apr 17 | United AirlinesLYB 16:0031h 13m2 stopsORD 23:13Little Cayman - Chicago | Sun, Apr 20 | Cayman AirwaysAED 3,24812% OFFAED 3,710 AED 3,248
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ORD 05:1512h 30m2 stopsLYB 17:45Chicago - Little Cayman | Fri, Apr 18 | United AirlinesLYB 08:5024h 35m2 stopsORD 09:25Little Cayman - Chicago | Fri, Apr 25 | Cayman AirwaysAED 3,26612% OFFAED 3,710 AED 3,266
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ORD 21:4017h 25m2 stopsLYB 15:05Chicago - Little Cayman | Sun, Mar 16 | United AirlinesLYB 16:0026h 6m1 stopsORD 18:06Little Cayman - Chicago | Sun, Mar 23 | Cayman AirwaysAED 3,27012% OFFAED 3,710 AED 3,270
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ORD 21:5019h 55m2 stopsLYB 17:45Chicago - Little Cayman | Thu, Apr 24 | United AirlinesLYB 08:5014h 50m2 stopsORD 23:40Little Cayman - Chicago | Mon, Apr 28 | Cayman AirwaysAED 3,28811% OFFAED 3,710 AED 3,288
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ORD 05:1512h 10m2 stopsLYB 17:25Chicago - Little Cayman | Sat, Apr 19 | United AirlinesLYB 17:3524h 32m1 stopsORD 18:07Little Cayman - Chicago | Sat, Apr 26 | Cayman AirwaysAED 3,3769% OFFAED 3,710 AED 3,376
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CHI 13:0017h 25m1 stopsLYB Invalid DateChicago - Little Cayman | Tue, Mar 18 | Normal AirlineLYB 15:006hNonstopCHI 16:00Little Cayman - Chicago | Thu, Mar 20 | Normal AirlineFind More FlightsFind More Flights
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ORD 21:4517h 20m2 stopsLYB 15:05Chicago - Little Cayman | Mon, Apr 28 | United AirlinesAED 1,679 AED 2,60436% OFF36% OFFAED 2,604 AED 1,679
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ORD 21:4536h 40m2 stopsLYB 10:25Chicago - Little Cayman | Mon, Apr 21 | United AirlinesAED 1,689 AED 2,60435% OFF35% OFFAED 2,604 AED 1,689
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ORD 21:4020h 5m2 stopsLYB 17:45Chicago - Little Cayman | Fri, Mar 21 | United AirlinesAED 1,977 AED 2,60424% OFF24% OFFAED 2,604 AED 1,977
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ORD 14:5026h 55m2 stopsLYB 17:45Chicago - Little Cayman | Fri, Mar 21 | American AirlinesAED 2,3709% OFFAED 2,604 AED 2,370
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CHI 13:0017h 25m1 stopsLYB Invalid DateChicago - Little Cayman | Tue, Mar 18 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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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 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 Little Cayman (LYB) cost?
According to Trip.com's data, the lowest price is around AED 3,283. -
How many airports are there in Little Cayman (LYB)?
There are 1 airport(s) near Little Cayman (LYB): Edward Bodden Airfield.
How to find a cheap flight from Chicago to Little 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 Little Cayman. Book your flights at the right time and save more.
Being flexible with your dates to get the cheapest Chicago to Little Cayman ticket.
Tap "Date" on flight search bar to get the calender for Chicago to Little Cayman airfare over next 6 months in 2025.
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Don't miss cheap Chicago to Little Cayman flight deals and promo codes.
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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.
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To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Little Cayman to get exclusive deals for you.
Flight Info | 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 |
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