Featured airlines
- Plan, book, fly with confidence
- Be in the knowGet alerts if flight prices drop or rise*
- Book smarterSave up to 30% on select hotels after you book a flight*
Cheap Flights from Chicago to Little Cayman (ORD-LYB)
Prices were available within the past 7 days and start at for one-way flights and $788 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Origin airport | O'Hare Intl. |
Destination airport | Edward Bodden Airfield |
Roundtrip price | $788 |
Distance | 1608 mi |
Chicago to Little Cayman Flights
The cheapest times to fly from Chicago to Little Cayman
On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Little Cayman are during the month of June. You can find some of the cheapest flights from Chicago to Little Cayman with Expedia's search tool and vast selection of airlines.
The best time to book a flight from Chicago to Little Cayman
Sunday is one of the best days to book for cheap flights from Chicago to Little Cayman: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.
How to find cheap round-trip tickets from Chicago to Little Cayman
Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Little Cayman in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.
Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Little Cayman flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.
You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Little Cayman airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.
*Terms apply.
Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.
Frequently asked questions
Explore a world of travel with Expedia
Flights
- Alaska Airlines Chicago (ORD) to Los Angeles (LAX) flights
- JetBlue Airways Chicago (ORD) to Fort Lauderdale (FLL) flights
- Spirit Airlines Chicago (ORD) to Dallas (DFW) flights
- Cayman Airways Miami (MIA) to Little Cayman (LYB) flights
- Spirit Airlines Chicago (ORD) to Tampa (TPA) flights
- Alaska Airlines Chicago (ORD) to Phoenix (PHX) flights
- JetBlue Airways Chicago (ORD) to New York (JFK) flights
- Spirit Airlines Chicago (ORD) to New York (LGA) flights
- JetBlue Airways Chicago (ORD) to Fort Myers (RSW) flights
- Flights from South Bend Intl.
- Flights from Dupage
- Flights from General Mitchell Intl.
- Flights from Midway Intl.
- Flights from Waukesha County
- Flights from Chicago Executive
- Flights from Greater Rockford
- Flights from Dane County Regional
- Flights from Goshen Municipal
- Flights from Kenosha Regional
- Swiss International Air Lines
- Viva Aerobus
- British Airways
- United
- Frontier Airlines
- Lufthansa
- Spirit Airlines
- Alaska Airlines
- Air Canada
- Delta
- Emirates
- Aeromexico
- JetBlue Airways
- American Airlines
- Turkish Airlines
- Volaris
- Flights to West Bay
- Flights to Little Cayman
- Flights to West End
- Flights to Colliers Bay
- Flights to Seven Mile Beach
- Flights to East End
- Flights to East End
- Flights to Spot Bay
- Flights to Tibbett's Turn
- Flights to Bodden Town
- Flights to George Town
- Flights to Rum Point
- Flights to North Side
- Flights to Blossom Village
- Flights from Chicago (ORD) to Atlanta (ATL)
- Flights from Chicago (ORD) to Guadalajara (GDL)
- Flights from Chicago (ORD) to Newark Liberty Intl. Airport (EWR)
- Flights from Chicago (ORD) to Honolulu (HNL)
- Flights from Chicago (ORD) to San Francisco (SFO)
- Flights from Chicago (ORD) to Miami (MIA)
- Flights from Chicago (ORD) to Orlando (MCO)
- Flights from Chicago (ORD) to Mexico City (MEX)
- Flights from Chicago (ORD) to San Juan (SJU)
- Flights from Chicago (ORD) to Los Angeles (LAX)
- Flights from Chicago (ORD) to Denver (DEN)
- Flights from Chicago (ORD) to San Diego (SAN)
- Flights from Chicago (ORD) to Toluca (TLC)
- Flights from Chicago (ORD) to Boston (BOS)
- Flights from Chicago (ORD) to Manila (MNL)
- Flights from Chicago (ORD) to Las Vegas (LAS)
- Flights from Chicago (ORD) to Punta Cana (PUJ)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from San Francisco (SFO) to Chicago (ORD)
- Flights from Houston (HOU) to Chicago (ORD)
- Flights from Dallas (DFW) to Chicago (ORD)
- Flights from Atlanta (ATL) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Minneapolis (MSP) to Chicago (ORD)
- Flights from Orlando (MCO) to Chicago (ORD)
- Flights from Philadelphia (PHL) to Chicago (ORD)
- Flights from Chicago (ORD) to Fort Lauderdale (FLL)
- Flights from Chicago (ORD) to Dallas (DFW)
- Flights from Denver (DEN) to Little Cayman (LYB)
- Flights from Fayetteville (XNA) to Little Cayman (LYB)
- Flights from Nassau (NAS) to Little Cayman (LYB)
- Flights from George Town (GCM) to Little Cayman (LYB)
- Flights from Miami (MIA) to Little Cayman (LYB)
- Flights from Dallas (DFW) to Little Cayman (LYB)
- Flights from Portland (PDX) to Little Cayman (LYB)
- Flights from Newark Liberty Intl. Airport (EWR) to Little Cayman (LYB)
- Flights from Houston (IAH) to Little Cayman (LYB)
- Flights from New York (JFK) to Little Cayman (LYB)
- Flights from Washington (IAD) to Little Cayman (LYB)
- Flights from Syracuse (SYR) to Little Cayman (LYB)
- Flights from Chicago (ORD) to Tampa (TPA)
- Flights from Chicago (ORD) to Seattle (SEA)
- Flights from Chicago (ORD) to Phoenix (PHX)
- Flights from Chicago (ORD) to New York (JFK)
- Flights from Chicago (ORD) to Houston (HOU)
- Flights from Chicago (ORD) to New York (LGA)
- Flights from Chicago (ORD) to Fort Myers (RSW)