Find cheap flights from Chicago to Islamorada - Compare and Save

When flying out of Chicago you’ll be using one of these airports: Chicago Midway, Chicago O'Hare Intl or Chicago Greater Rockford. Islamorada does not have its own airport so you’ll be flying into nearby Miami airport, which is 63.9 mi away.

Direct flights cover the 1,186 miles separating Chicago and Islamorada in about 3h 00m.

75 direct flights run between Chicago and Islamorada on a daily basis. On average, there are about 528 departures each week.

Consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Saturdays.

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Islamorada.

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Islamorada from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Islamorada with an airline and back to Chicago with another airline.

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Islamorada from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

In the last 5 days, the cheapest one-way ticket between Chicago and Islamorada found on KAYAK was with Frontier for $29. Frontier offered a round-trip connection from $57 and JetBlue from $89.