Cheap flights from Chicago to Key West

Chicago FSS
CHI
Key West
EYW

Flight deals from Chicago to 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 $134.

Top 10 cheap flights from Chicago to Key West

About the Chicago — Key West flight

Looking for cheap flights from Chicago to Key West? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — Key West ticket online at the best price.

The route has direct flights — around 29 flights per week, flights are operated by United Airlines, American Airlines, a nonstop flight takes about 3 h 21 min, the distance between the cities is around 1,996 km.

Planning your trip? You may find our Key West travel guide, how to get from the airport into town and Key West weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $134Min. price
SeptemberCheapest
NovemberPeak season
YesDirect flights
1,996 kmDistance
3 h 21 minTravel time
2Airlines
29 / wkFlights

Flight schedule from Chicago to Key West

The table shows direct flights from Chicago to Key West on the selected date. The flight takes approximately 3 h 21 min. Regular flights are operated by United Airlines and American Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Key West International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

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Last update: 25 Aug 2026

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 $134 in September, and the most expensive are around $293 in November. 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.

 
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Prices by month

Average one-way fares from Chicago to Key West by month. Tickets are usually cheapest in September (around $122) and priciest in March (about $173) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$154highMay$145mediumSep$122low
Feb$159highJun$136mediumOct$126low
Mar$173highJul$140mediumNov$136medium
Apr$150mediumAug$136mediumDec$168high

Some values are estimated based on seasonality.

When to fly

Weather in Key West: it is warmest in August (up to 29 °C on average) and coolest in January (around 22 °C). The driest month is February.

Tickets are usually cheapest in September and most expensive in November. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · Key West

Dry and wet days · Key West

Wind speed and direction · Key West

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

  • Book ahead: fares for Chicago — Key West are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to Key West is usually September — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — Key West route are operated by 2 airlines; United Airlines runs the most flights (around 52% of all flights). Compare carriers, flight shares and schedules below.

  • United AirlinesUA
    5x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → EYW5x/week
    51.7%Open →
  • American AirlinesAA
    5x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → EYW5x/week
    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

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Frequently asked questions about the Chicago — Key West flight

How long is the flight from Chicago to Key West?

A nonstop Chicago — Key West flight takes about 3 h 21 min — the distance between the cities is around 1,996 km.

How far is it from Chicago to Key West?

The distance from Chicago to Key West is about 1,996 km, which a nonstop flight covers in around 3 h 21 min.

Are there direct flights from Chicago to Key West?

Yes, there are nonstop flights Chicago — Key West — around 29 flights per week.

Which airlines fly from Chicago to Key West?

Airlines operating Chicago — Key West include United Airlines, American Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — Key West flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Key West International Airport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to Key West?

The price of a Chicago — Key West ticket depends on your travel date, season and demand: it is usually cheapest to fly in September, and most expensive in November. Tickets typically cost between $134 and $293. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — Key West?

Flights Chicago — Key West are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is September. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to Key West?

To catch a low fare Chicago — Key West, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually September.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

Where else you can fly from Chicago

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New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverLondonNashvilleIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityPhoenixMiamiLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester

Where else you can fly from Key West

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Washington, D.C.DallasAtlantaPhiladelphiaBostonNew York CityFort LauderdaleCharlotteMiamiTampaNew HavenHoustonOrlandoCancunTallahasseeNassauGainesville

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