Cheap flight deals from Chicago to Little Cayman Starting at AED 1,681

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

When is the cheapest time to fly from Chicago to Little Cayman?

We monitor flight fares to help you find the best deals effortlessly

Cheapest flights
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  • 16 23
  • 23 30

  • Apr

    30 6
  • 6 13
  • 13 20
  • 20 27

  • May

    27 4
  • 4 11
  • 11 18
  • 18 25

  • Jun

    25 1
  • 1 8
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • 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 3,288.

  • 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.
1
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.
2
Compare cheap Chicago to Little Cayman flight deals from over hundreds of airlines.
Compare prices from over 500 airlines with our powerful search and find the cheapest flight tickets from Chicago to Little Cayman.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Little Cayman route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Little Cayman flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
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.
6
Search for flights on the go.
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
Peak season for travel March
Flight distance 2,570.08 km
Popular airline United Airlines

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