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Cheap Flights from Chicago to Little Cayman, KY, Cayman Islands - CHI to LYB Last modified: Jul 28, 2016 1:13 AM

Popular flights from Chicago to Little Cayman Last modified: Jul 28, 2016 1:13 AM

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

United
CHILYB
Thu 9/8
3 stops
LYBCHI
Mon 9/12
3 stops
$740
Select

How Much Does it Cost to Fly from Chicago to Little Cayman (CHI to LYB)?

We have collected flight cost data from across the web for travel from Chicago to Little Cayman, and have found the average flight price for this trip to be $2,470.

When Can I Buy the Cheapest Flight from Chicago to Little Cayman (CHI to LYB)?

Airlines can adjust prices for plane tickets from Chicago to Little Cayman based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

Airports for Your Route

These pages contain information about the major airports in Chicago and Little Cayman, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Key West American, JetBlue, United $358
Chicago to San Juan Silver, American, Alaska, JetBlue, Frontier, Spirit, United $274
Chicago to Sarasota - Bradenton American, United $191
Chicago to Jacksonville American, JetBlue, United $274
Chicago to Charleston American, JetBlue, United $228
Chicago to Daytona Beach American $211
Chicago to Panama CityCheck Dates

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Montego Bay Silver, American, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America $388
Chicago to Grand Cayman American, JetBlue, Cayman, United $383
Chicago to Kingston Silver, American, JetBlue, Spirit, United $599
Chicago to Punta Cana American, Alaska, JetBlue, Frontier, Spirit, Sun Country, United $318
Chicago to Nassau Silver, American, JetBlue, Frontier, Spirit, United, Bahamasair $370
Chicago to Cozumel American, AeroMexico, Alaska, Sun Country, United, Volaris $408
Chicago to Guadalajara Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, United, Virgin America, Volaris $277
Chicago to St Thomas Island American, JetBlue, Spirit, United $307
Chicago to Belize City Tropic Air, American, Alaska, United $367
Chicago to Aruba Silver, Insel Air Aruba, American, JetBlue, Spirit, United $393
Chicago to Puerto Plata American, JetBlue, United $565
Chicago to Guatemala City American, Alaska, Spirit, United $426
Chicago to Puerto Vallarta American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, Volaris $352

Cheap Domestic Flights to Little Cayman - LYB

FlightsAirlineLowest Price
Indianapolis to Miami American, Frontier, United $169
Milwaukee to Miami American, United $291
Indianapolis to Orlando American, Alaska, Frontier, United $97
Milwaukee to Orlando American, Alaska, Frontier, United $107
Indianapolis to Ft Lauderdale American, United $237
Milwaukee to Ft Lauderdale American, Alaska, Frontier, United $288

Cheap International Flights to Little Cayman - LYB

FlightsAirlineLowest Price
Indianapolis to Grand Cayman American, Cayman, United $497
Milwaukee to Grand Cayman American, Cayman, United $543
Indianapolis to Montego Bay American, Allegiant, Spirit, United $409
Milwaukee to Montego Bay American, Frontier, Spirit, United $415
Cheap Flights from Chicago to Little Cayman, KY, Cayman Islands, from $740 Round trip from CHI to LYB