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

Flight FAQs

From Key West to Chicago

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

What safety measures are being taken by airlines flying from Key West to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. New policies for travelers booking flights from Key West to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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

Due to the rapidly changing circumstances due to COVID-19, airlines like American Airlines, United Airlines, and Delta flying from Key West to Chicago have implemented new flexible cancellation policies.

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

Yes, there are multiple flights from Key West to Chicago for under $300. The cheapest flight booked recently is on United Airlines for just $219, but on average you can expect to pay $291.

Are there nonstop flights from Key West to Chicago for under $300 on Cheapflights?

Cheapflights has at least 9 direct flights from Key West to Chicago under $300. A good price for a nonstop flight from Key West to Chicago is less than $687.

Are there last-minute flights available from Key West to Chicago for under $400?

There are currently 6+ open flights from Key West to Chicago within the next 7 days for less than $400.

Is Key West weather warmer or cooler than Chicago?

Our data indicates that the weather will be 91 °F on average in the month of August. The temperature in Chicago is typically colder than in Key West. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.

How long is the flight from Key West to Chicago?

Airlines like United Airlines, American Airlines, and Delta fly from Key West to Chicago in about 3h 25m. The time it takes to get you to your destination can typically vary by up to 1h 42m. This flight may include one or multiple stops.

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

Currently priced at $219, United Airlines will fly you from Key West to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Delta - these airlines can fly you to your destination from $294 and $313, respectively. United Airlines is currently priced 46% below the average price you’ll pay for this route.

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

For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $127. Users have also found prices from $148 and $157 on JetBlue and American Airlines, respectively.