Cheap flights from Chicago (CHI) to Cayman Islands

Flight FAQs

From Chicago to Cayman Islands

Are flight prices decreasing from Chicago to Cayman Islands due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Cayman Islands for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Chicago to Cayman Islands for under $400 on Cheapflights?

Yes, there are multiple flights from Chicago to Cayman Islands for under $400. The cheapest flight booked recently is on JetBlue for just $378, but on average you can expect to pay $425.

Are there nonstop flights from Chicago to Cayman Islands for under $600 on Cheapflights?

Cheapflights has at least 3 direct flights from Chicago to Cayman Islands under $600. A good price for a nonstop flight from Chicago to Cayman Islands is less than $570.

How popular is this flight route?

The Chicago to Cayman Islands flight path was viewed by 20 users in the past month. Keep an eye out for changes in search interest prior to high and low season.

What are the most popular airlines that fly from Chicago to Cayman Islands?

Before booking your flight from Chicago to Cayman Islands check out the most popular airlines for this route: Major Airline, American Airlines or JetBlue.

What are the most popular routes from Chicago to Cayman Islands?

While some choose either Chicago Midway - George Town Owen Roberts Intl or Chicago O'Hare Intl - Cayman Brac Gerrard-Smith, Chicago O'Hare Intl - George Town Owen Roberts Intl is the most popular route from Chicago to Cayman Islands.

What are the cheapest Flights from Chicago to Cayman Islands?

Looking for the cheapest flight from Chicago to Cayman Islands? While on average our users pay $407, our data indicates the cheapest price to be $159. The most popular route (Chicago O'Hare Intl - George Town Owen Roberts Intl), is priced around $402.