Cheap flights from Chicago to Jamaica

How to find cheap flights from Chicago to Jamaica

Looking for flight tickets from Chicago to Jamaica? Round-trip tickets start from C$377 and one-way flights from Chicago to Jamaica start from C$138

Here are some tips on how to secure the best flight price and make your journey as smooth as possible.

• Simply hit "search." From American Airlines to international carriers like Emirates, we've compared flights from all major airlines and online travel agents to find the cheapest Chicago to Jamaica flights. And with us, there are no hidden fees – what you see is what you pay.
   
• Compare cheap Chicago to Jamaica flight deals from over 1,000 providers. Then choose the cheapest plane tickets or fastest journeys. Flight tickets to Jamaica start from C$138 one-way.
• Flex your dates to secure the best fares for your Chicago to Jamaica ticket. If your travel dates are flexible, use Skyscanner's "Whole month" tool to find the cheapest month, and even day to fly from Chicago to Jamaica.
    
• Set up a Price Alert. We price-check with over 1,000 travel companies so you don't have to. You can easily track the price of your airline tickets from Chicago to Jamaica by creating an alert. Whenever prices go up or down, you'll get an email or push notification to help make sure you get the best possible flight deal.
• Look for direct flights. Only interested in direct flights from Chicago to Jamaica? Make sure to tick "Direct flights only" when performing a search. If there are direct Chicago to Jamaica flights available, these will appear in the results.
• Find the cheapest Business Class flights from Chicago to Jamaica. Check the difference in price of your plane ticket to Jamaica from Chicago when traveling in Economy, Premium Economy, Business or First Class. Note that not all cabin classes are available for every destination or airline.
• Include nearby airports in your search. Widen your search for Chicago to Jamaica flight deals by selecting the "add nearby airports" option. This will allow you to see flight prices for all the nearest airports at your departure and destination point and could help you save money.
• Search for flights on the go. To get the best flight booking experience on the go, download our app and search for cheap flight tickets from Chicago to Jamaica when out and about.

Combine your flight from Chicago to Jamaica with hotels and car rental

Once you've secured your plane ticket, we'll also help you discover the best prices and exclusive rates for hotels in Jamaica or close by. Lastly, compare hundreds of car rental companies at once so that you get the best car rental deals for your trip.

Compare Chicago to Jamaica flight tickets with other routes using the everywhere search

Not quite yet set on flying to Jamaica from Chicago? You can easily browse other destinations by searching flights to "Everywhere" – this will allow you to find the cheapest place to travel to.