Cheap Flights from Chicago O'Hare International to Key West International

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Flight deals from Chicago O'Hare International to Key West International

Looking for a cheap last-minute deal or the best return flight from Chicago O'Hare International to Key West International? Find the lowest prices on one-way and return tickets right here.

Direct flights from Chicago O'Hare International to Key West International

Chicago O'Hare International to Key West International: Alternative routes

Compare routes from Chicago O'Hare International to Key West below. You may find an airport to fly into that's cheaper, faster, or easier than Key West International.

Chicago to Key West: Flight information

The things to know before you go.
Cheapest flight foundR 4,672
Cheapest month to flyOctober
Average flight time3 hrs, 18 mins
Most popular airlineEnvoy Air
Average flights per week21

Finding cheap flights from Chicago O'Hare International to Key West International: Frequently asked questions

The best price we found for a return flight from Chicago O'Hare International to Key West International is R 4,778. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
3 hours and 18 minutes is the average flight time from Chicago O'Hare International to Key West International.
Envoy Air, American Airlines and Air New Zealand fly direct from Chicago O'Hare International to Key West International.
As of May 2025, there are 21 flights per week flying from Chicago O'Hare International to Key West International.
The cheapest month to fly from Chicago O'Hare International to Key West International is usually May 2025.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Chicago O'Hare International Airport to Key West International Airport on Saturday, 16 August 2025.
Yes – the average flight time is 3 hours and 18 minutes.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Key West International but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Key West is around 40 days in advance, so don’t leave your flight to the last minute.
Currently, Delta and United offer the cheapest flight tickets to Key West International.

Travelling from O'Hare International Airport (ORD) to Key West International Airport (EYW): what you need to know

  • Your ORD to EYW flight won't wait if you're running late, so don't forget to check in on time. Arrive up to one hour in advance for domestic flights and two hours ahead for international travel.

  • Travelling during a peak time such as August? School holidays and other high seasons can lead to longer queues and delays at airport checkpoints. Be extra cautious and arrive up to four hours ahead of international flights and two hours before a domestic departure.

  • Flying into Key West (and then discovering more of United States!) is easy with American Airlines. This popular carrier has direct flights from O'Hare International Airport to Key West International Airport.

  • Most travellers choose to travel with American Airlines on this route.

  • American Airlines is the most punctual carrier that operates ORD to EYW flights, with 78.33% of its services arriving as scheduled.

  • We make it simple to book a flight with a stopover. To see all your options for tickets from O'Hare International Airport to Key West International Airport, uncheck 'Direct flights only.' Then, pick a flight with a stop long enough to visit your chosen city. Popular stopovers between ORD and EYW include:

    • Hartsfield-Jackson Atlanta International Airport

    • Cincinnati/Northern Kentucky Airport

    • Asheville Regional Airport

How to find the cheapest flights from O'Hare International Airport (ORD) to Key West International Airport (EYW)

  • Currently, R 4,672 is the lowest price we've seen for a one-way O'Hare International Airport to Key West International Airport flight. The best price for a return ticket is R 4,778. Keep in mind that fares could change due to availability at the time of booking.

  • It's usually best to book ahead of time if you're hoping to get cheap tickets from ORD to EYW. That's because airlines adjust prices based on demand, which tends to increase closer to the date of departure.

  • Finding cheap flights from O'Hare International Airport to Key West International Airport is easier if you're flexible with your travel plans. Use the 'Whole month' search function to see the lowest fares across every month and snap up a great deal.

  • You won't have to check every day to find out if fares have dropped when you create a Price Alert. We'll notify you the moment there's a better deal on cheap flights from ORD to EYW.

  • Find the right flight for you by using the filters. To see the 'Best,' 'Fastest' or 'Cheapest' flights from O'Hare International Airport to Key West International Airport, use the 'Sort by' tool. You can also filter results by airline, arrival and departure times, and number of stops.

Handy information about O'Hare International Airport (ORD)

  • ORD's address is 10000 West O'Hare.

  • When it comes to the on-time performance of O'Hare International Airport, 74.85% of flights arrive within the expected timeframe.

  • Central Chicago to O'Hare International Airport is around 40 kilometres. Depending on traffic, it'll take about 35 minutes to get there if you're ride-sharing, catching a cab or driving.

  • Planning to catch public transport? You can expect a journey time of around 55 minutes.

  • Get your holiday off to a relaxed start by staying near ORD. Whether you're boarding an early flight from O'Hare International Airport to Key West International Airport or just don't want to be rushed, these hotels are the answer:

Arriving at Key West International Airport (EYW)

Getting from Key West International Airport (EYW) to central Key West

  • EYW is located at 3491 South Roosevelt Boulevard.

  • Key West International Airport is roughly 3 kilometres from the centre of Key West. Driving there takes about 5 minutes.

  • Travelling on public transport takes roughly 40 minutes.

When to fly to Key West International Airport (EYW)

  • The quietest month for a flight from O'Hare International Airport to Key West International Airport is February, while January is the most popular. Choose the ideal time to go to Key West based on whether you prefer a laid-back vibe or a more bustling atmosphere.

  • The warmest month in Key West is August, with temperatures ranging between 26ºC (79ºF) and 30ºC (86ºF). Book your flights from O'Hare International Airport to Key West International Airport in this month if this is the type of weather you enjoy.

  • If you want to travel in cooler conditions, look for a cheap ticket from ORD to EYW in January. Temperatures average between 18ºC (64ºF) and 23ºC (73ºF) then.

Explore more of United States

  • Key West has loads to offer, but there are so many other corners of United States just waiting to be explored. Around 209 kilometres north-east of Key West, a trip to Miami will keep you on the go. Start with attractions like Wynwood Walls, Vizcaya Museum and Gardens and American Airlines Arena.

  • If you're looking to explore another well-known destination in United States, consider Tampa, about 386 kilometres north of Key West. Ybor City Tattoo Company, Tampa Riverwalk and The Florida Aquarium are key highlights.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.