EYW to CHI, Key West International Airport to Cheap Flights

Based on HopeGoo data, Delta Air Lines offers one-way fares as low as US$86 on Cheapest nonstop routes (e.g. EYW to ORD on Thu, Mar 5), while Spirit Airlines offers Cheapest nonstop round-trips from US$197 departing on Thu, Mar 12 and returning on Tue, Mar 17.

It takes about 3 hours 31 minutes to fly from Key West to Chicago.

By analyzing data from all airlines on the HopeGoo flight calendar, it looks like the best time to book a flight from Key West to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.

To find best deals on flights from Key West to Chicago, you can use various tools on HopeGoo: · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Thu, Mar 5, with one-way flights priced at just US$86. · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is United Airlines. · Set up price alerts to easily monitor ticket prices without having to check every day. · Check HopeGoo flight deals and promo codes frequently. · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July. · Get exclusive promo codes for HopeGoo app users.

The cheapest months to fly from Key West to Chicago is October, when demand for travel is lower.

After crunching the numbers on our February flight calendar, it's currently cheapest to fly from Key West to Chicago on February 27, 2026 with Spirit Airlines, with prices starting at US$339.

The time difference between Chicago and Key West is 1h.

Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your HopeGoo, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.