On this page, you can find and buy flight tickets from Key West to Chicago. The distance between these cities is 1,996 km, and flight frequency averages 11 flights per week.
Flights on this route are provided by United Airlines and American Airlines. To plan your budget, explore the low-price calendar and price trend chart, as well as information on how to get to the airport of departure and how to get from the airport to your destination.
Below is a calendar of the lowest flight ticket prices for Key West — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 342 in F, and the most expensive are around AED 1,223 in r. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.
Key West → Chicago, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | AED 809 | low | May | AED 957 | medium | Sep | AED 809 | low |
| Feb | AED 920 | medium | Jun | AED 993 | medium | Oct | AED 846 | low |
| Mar | AED 1,141 | high | Jul | AED 1,030 | medium | Nov | AED 883 | medium |
| Apr | AED 1,104 | high | Aug | AED 846 | low | Dec | AED 1,141 | high |
Some values are estimated based on seasonality.
The warmest months in Chicago are July and August, when daytime temperatures reach 26.5°C. The coldest period is January, with temperatures dropping to -5°C, and peak precipitation is observed in May.
The most budget-friendly flights are available in September — ticket prices start AED 337. A price peak is recorded in December, when offers start AED 1,206.
September is the optimal choice for a trip: it offers a great compromise between a comfortable temperature of around 23°C and minimum ticket costs. It is best to avoid May and October due to the high probability of rain.
Regular air service between Key West and Chicago is provided by 2 airlines, operating a total of about 11 flights per week. The main carriers on this route are United Airlines and American Airlines. You can find detailed information about departure times, direct flight availability, and layover options in the interactive list below by clicking on the airline card.
Flights Key West — Chicago depart from Key West International Airport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
A direct flight covers the 1,996 km distance in approximately 2 hours 30 minutes. Connecting flights can take 5 hours or more.
Regular flights from Key West to Chicago are operated by United Airlines and American Airlines.
Yes, direct flights are available on this route, though their frequency depends on the season. Check the airlines section for the current schedule on your selected date.
Prices change constantly depending on demand. You can find the current minimum, for example from 7,230 ₽, in the low-price calendar on this page.
Flights from Key West typically arrive at O'Hare International Airport (ORD) or Midway International Airport (MDW), which serve Chicago.
Where travelers fly most — pick a route and check prices
