Cheap flights from Chicago to Key West (CHI - EYW)

Flight FAQs

From Chicago to Key West

Are flight prices decreasing from Chicago to Key West 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 Key West 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.

Which airlines flying from Chicago to Key West have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Key West that may be offering flexible cancellation policies are American Airlines, United Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

What airport do you fly into for flights to Key West from Chicago?

Located just 2.6 mi from the city center, Key West is the airport most travelers will use when flying to Key West from Chicago. Booking flights from Chicago to Key West (EYW) should be relatively easy as there are 3 daily inbound flights from Chicago from 4 different airlines.

Can I find flights from Chicago to Key West for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Key West for under $300. The cheapest flight booked recently is on Multiple Airlines for just $215, but on average you can expect to pay $262.

Are there nonstop flights from Chicago to Key West for under $400 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Key West under $400. A good price for a nonstop flight from Chicago to Key West is less than $424.

Are there last-minute flights available from Chicago to Key West for under $300?

There are currently 20+ open flights from Chicago to Key West within the next 7 days for less than $300.

What days are nonstop flights available from Chicago to Key West?

Days when nonstop flights are available for this flight are: Tuesday.

How many flights depart from Chicago to Key West on average per day?

Travelers can expect 2 flights from Chicago to Key West on average per day.
Morning (6am - Noon) - 100% of flight departures

Is Chicago weather warmer or cooler than Key West?

Temperatures around the 91 °F's can be experienced in August. The weather in Key West is hotter than in Chicago. Plan for potential changes in flight availability as peak weather approaches in this location.

How long is the flight from Chicago to Key West?

A quick flight from Chicago to Key West can take about 4h 45m. Delta provides one of the quickest options available for as low as $597. The distance from Chicago to Key West is about 1261 mi.

What are the cheapest airlines flying from Chicago to Key West round-trip?

Currently priced at $245, American Airlines will fly you from Chicago to Key West and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $277. Users have found that American Airlines is 42% cheaper than the other options available to this destination.

What are the cheapest airlines to fly from Chicago to Key West one-way?

The cheapest airlines for a one-way flight from Chicago to Key West are American Airlines ($128), United Airlines ($144), and Allegiant Air ($149).