Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Cheapest time to fly from Key West, FL to Chicago

Flexible with dates? We find the best price for the week of the day you select *Prices may vary after you search.

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week: Jan 12 - Jan 18

Flights from just $306

$434

$344

$451

$337

$306

$308

$352

$401

$426

$444

$403

$491

DecemberJanuaryFebruaryMarch

Cheapest flight$85The best price for flights from Key West, FL to Chicago offered by eDreams, which have been found by our customers in the last 3 days

Departure AirportKey WestKey West is where you'll take off when flying from Key West, FL to Chicago

Arrival AirportO'hare International AirportYou'll land at O'hare International Airport when flying from Key West, FL to Chicago

Peak seasonJuneJune is the busiest time to fly from Key West, FL to Chicago according to search data results from our customers

Airlines operating this routeAmerican AirlinesAirline(s) that fly from Key West, FL to Chicago

Best time to bookMayMay is one of the most frequent times to fly to Chicago from Key West, FL according to real data from our customers

Distance: 1241 miles

Key West, FL airports

Key West (EYW)How far from city center: 1 miles

Chicago airports

O'hare International Airport (ORD)How far from city center: 14 miles

Midway Airport (MDW)How far from city center: 4 miles

Are you planning to travel to Chicago for vacations, business or family visits? eDreams offers you the cheapest flights and best deals departing from Key West, FL. With our fast search engine you will get a large selection of airfares from standard and low cost airlines worldwide and easily book your tickets for this route. If you are flexible we help you identify the cheapest day to fly to Chicago and if you need to leave soon you can check our most convenient last minute fares. Read all the useful information about your next destination and proceed to the reservation, indicating your flight dates and completing your travel booking with hotels and car rental!

Frequently asked questions about flights from Key West, FL to Chicago

What are the benefits of booking flexible flight tickets?

Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. At eDreams have you covered!

For flights from Key West, FL to Chicago, how can I find the cheapest price?

The cheapest price for a flight from Key West, FL to Chicago is $85. At eDreams we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.

When booking, when is the best time to get the best prices for flights from Key West, FL to Chicago?

The most popular months to book a trip from Key West, FL to Chicago are May, December and August, based on the searches of our customers.

When is the best time to travel from Key West, FL to Chicago?

The best time of the year to visit Chicago depends on lots of personal preferences, especially the price. Regarding popularity, June is the best month to fly to Chicago from Key West, FL in terms of searches from our customers, followed by August and May. If you prefer to avoid the busy season and get away from the crowds May, August and June are the months with fewer searches for Key West, FL - Chicago.

Which airports have flights between Key West, FL and Chicago?

The main route from Key West, FL to Chicago is: Key West (EYW) to O'hare International Airport (ORD). The following airlines fly this route:

American Airlines.

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