Support

Flights Chicago — Key West

Chicago
CHI
Key West
EYW

Cheap flights Chicago — Key West

Below you can see the best deals on flights Chicago — Key West for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 1 September, from AED 532.

Top 10 cheap flights Chicago — Key West

Direct flights Chicago — Key West

Direct flight options for Chicago — Key West with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight takes around 3 h 21 min.

Top 10 direct flights Chicago — Key West

About the Chicago — Key West flight

On this page, you can find and book flights from Chicago to Key West. The distance between the cities is 1,996 km, with about 10 regular flights per week. To plan your trip, use the information on how to get to the airport of departure and how to get from the airport to the center of Key West.

Flights on this route are operated by UA and AA. Keep in mind that ticket prices are dynamic and depend on the booking date, so we recommend using the low-price calendar and price trend chart on this page to find the best deal.

Flight ticket prices by day: Chicago — Key West

Below is a calendar of the lowest flight ticket prices for Chicago — Key West by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 532 in F, and the most expensive are around AED 1,165 in b. 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.

 
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--
--

Prices by month

Chicago → Key West, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 619highMayAED 582mediumSepAED 488low
FebAED 638highJunAED 544mediumOctAED 507low
MarAED 694highJulAED 563mediumNovAED 544medium
AprAED 601mediumAugAED 544mediumDecAED 676high

Some values are estimated based on seasonality.

When to fly

The hottest weather in Key West occurs in July and August, when temperatures reach 29°C. September is considered the wettest month (with over 190 mm of rainfall), while the most comfortable and dry conditions for a trip are from December to March, when the average temperature is around 22°C.

In terms of savings, September is the most economical month to fly, with prices starting AED 532. Costs peak in November, when the minimum fare rises to AED 1,165, while in early summer, tickets cost AED 1,150.

October is a good compromise: the flight cost starts AED 991 with moderate rainfall. For guaranteed dry weather, it's better to choose February with prices starting AED 1,064, avoiding the expensive November period.

Temperature · Key West

Dry and wet days · Key West

Wind speed and direction · Key West

We'll let you know if you need a visa

Enter your destination or
Your nationality
Destination

How to get the best deal on a Chicago — Key West ticket

  • Book your tickets at least 4–6 weeks before departure, as there are only about 10 flights per week on this route, and the most affordable United Airlines and American Airlines fares sell out quickly.
  • Try to choose mid-week flights, as trips to the resort of Key West on Fridays and Sundays are traditionally more expensive.
  • Use the price trend chart and calendar on this page to find dates when ticket prices drop to as low as AED 532.
  • Pay attention to fare rules: major carriers on this route often offer "no-baggage" fares, so check the cost of checked luggage in advance.

Airlines

Two major airlines operate on this route — United Airlines and American Airlines — providing a combined total of about 10 flights per week. Most flights are direct, ensuring a quick connection between the cities, though flight frequency may vary based on seasonal demand. Below is a detailed list of carriers with up-to-date schedules and information on available route options.

  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → EYW5x/week
      Duration
      3h 24m
      Days
      MTWTFSS
    51.7%Open →
  • American AirlinesAA
    5x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → EYW5x/week
      Duration
      3h 23m
      Days
      MTWTFSS
    48.3%Open →

Cities and airports on the Chicago — Key West route

Flights Chicago — Key West depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Key West International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Key West

EYW
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

Interesting articles about Key West

View all
Interesting

Top Cosmodrome Tours

USA Cape Canaveral and Kennedy Space Center The Kennedy Space Center is one of the world’s main spaceports. A rocket park and a museum complex with space attractions are open to visitors, however, mos…

Free Public Transport AbroadUseful information

Free Public Transport Abroad

How to get around abroad is always a tricky question. Some simply buy a day pass and spare no expense, while others prefer to walk to avoid spending extra money on “it’s only a ten-minute walk!”. But…

What Tour Guides Don’t Talk About?Tips for Travelers

What Tour Guides Don’t Talk About?

Do you like engaging excursions? Everyone loves them. And what spices up the list of historical facts about a landmark? Legends, of course! We’ve tried to gather interesting legends about some landmar…

Interesting

10 Most Unusual Beaches in the World

Do you love beach holidays but are tired of ordinary beaches? Read our review of the ten most unusual beaches in the world; they will surely not leave you indifferent. 1. Glass Beach, Fort Bragg, Cali…

Gadgets for Sophisticated TravelersInteresting

Gadgets for Sophisticated Travelers

Remember the cartoon about the resourceful Inspector Gadget, who handled any extreme situation in a matter of seconds? All he had to do was give a command, and wheels would instantly appear from his s…

Abandoned Cities: 5 Places Where Time Stood StillUseful information

Abandoned Cities: 5 Places Where Time Stood Still

Sometimes a trip needs a little adrenaline. And you don’t necessarily have to parachute, paraglide over the city (which is also very cool!) or provoke local bandits by walking alone in dark alleys. Yo…

View all

Frequently asked questions about the Chicago — Key West flight

How long is the flight from Chicago to Key West?

The average direct flight time for the 1,996 km distance is about 2 hours and 25 minutes. The actual duration may vary slightly depending on the type of aircraft.

Which airlines fly this route?

Regular air service between the cities is provided by United Airlines and American Airlines.

Are there direct flights?

Yes, direct non-stop flights are available on this route, which is the most convenient and fastest way to reach the islands.

How much is the cheapest ticket?

Airfare prices change constantly depending on the season and demand. You can find the current minimum for the coming months in the low-price calendar on this page.

Which airport do flights arrive at?

All flights on this route arrive at Key West International Airport (EYW), located within the city limits.

Where else you can fly from Chicago

See all
New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from Key West

See all
Washington, D.C.DallasAtlantaPhiladelphiaBostonNew York CityFort LauderdaleCharlotteMiamiNew HavenTampaHoustonOrlando
We use cookies for your convenience.