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

Compare Chicago O'Hare International to Key West International flight deals

Find the cheapest month or even day of the year to fly 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 Airport to Key West International Airport? If you want to travel next month, return fares start from R 4,147. Find the lowest prices on one-way and return tickets right here.
Key West.R 1,889 per passenger.Departing Tue, 18 Aug.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Tue, 18 Aug, arriving in Key West International.Price includes taxes and charges.From R 1,889, select.
Key West.R 1,983 per passenger.Departing Sat, 26 Sep.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 26 Sep, arriving in Key West International.Price includes taxes and charges.From R 1,983, select.
Key West.R 2,227 per passenger.Departing Sat, 24 Oct.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Key West International.Price includes taxes and charges.From R 2,227, select.
Key West.R 2,998 per passenger.Departing Mon, 9 Nov.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon, 9 Nov, arriving in Key West International.Price includes taxes and charges.From R 2,998, select.
Key West.R 3,042 per passenger.Departing Tue, 18 Aug.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Tue, 18 Aug, arriving in Key West International.Price includes taxes and charges.From R 3,042, select.
Key West.R 3,334 per passenger.Departing Sat, 5 Dec.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat, 5 Dec, arriving in Key West International.Price includes taxes and charges.From R 3,334, select.
Key West.R 4,724 per passenger.Departing Sat, 24 Oct.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 24 Oct, arriving in Key West International.Price includes taxes and charges.From R 4,724, select.
Key West.R 4,725 per passenger.Departing Thu, 5 Nov.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 5 Nov, arriving in Key West International.Price includes taxes and charges.From R 4,725, select.
Key West.R 4,727 per passenger.Departing Tue, 1 Dec.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 1 Dec, arriving in Key West International.Price includes taxes and charges.From R 4,727, select.
Key West.R 4,785 per passenger.Departing Sun, 24 Jan.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun, 24 Jan, arriving in Key West International.Price includes taxes and charges.From R 4,785, select.
Key West.R 4,789 per passenger.Departing Mon, 7 Jun.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Mon, 7 Jun, arriving in Key West International.Price includes taxes and charges.From R 4,789, select.
Key West.R 5,609 per passenger.Departing Sat, 26 Sep.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 26 Sep, arriving in Key West International.Price includes taxes and charges.From R 5,609, select.
Key West.R 13,788 per passenger.Departing Thu, 11 Feb.One-way flight with United.Outbound indirect flight with United, departs from Chicago O'Hare International on Thu, 11 Feb, arriving in Key West International.Price includes taxes and charges.From R 13,788, select.
Key West.R 15,063 per passenger.Departing Sat, 20 Mar.One-way flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 20 Mar, arriving in Key West International.Price includes taxes and charges.From R 15,063, select.
Key West.R 16,569 per passenger.Departing Thu, 11 Feb.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 11 Feb, arriving in Key West International.Price includes taxes and charges.From R 16,569, select.
Key West.R 28,004 per passenger.Departing Sat, 20 Mar.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 20 Mar, arriving in Key West International.Price includes taxes and charges.From R 28,004, select.

Find the cheapest month to fly from Chicago O'Hare International to Key West International

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Chicago O'Hare International to Key West International flights are currently cheapest in August.
Aug
from R 1,889
Sep
from R 1,983
Oct
from R 2,227
Nov
from R 2,998
Dec
from R 3,334
Jan
from R 4,785
Feb
from R 13,788
Mar
from R 15,063
Apr
Find prices
May
Find prices
Jun
from R 4,789
Jul
Find prices

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.

Key West International

5km from central Key West
ClosestCheapest
from R 1,889
Search flights

Chicago to Key West: Flight information

The things to know before you go.
Cheapest flight foundR 1,889
Cheapest month to flyAugust
Average flight time3 hrs, 22 mins
Most popular airlineAmerican Airlines
Average flights per week52

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 4,147. 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 22 minutes is the average flight time from Chicago O'Hare International to Key West International.
American Airlines, Envoy Air and United fly direct from Chicago O'Hare International to Key West International.
As of August 2026, there are 52 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 September.
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, 5 September 2026.
Yes – the average flight time is 3 hours and 22 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, Frontier Airlines and American Airlines offer the cheapest flight tickets to Key West International.

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

  • Jump on a direct flight from Chicago O'Hare International Airport to Key West International Airport and you'll be in the air for an average of 3 hours 20 minutes.

  • You can choose from 16 weekly Chicago O'Hare International Airport to Key West International Airport flights. The 07:10 departure with United Airlines is the earliest available. United Airlines operates the latest service of the day at 18:00.

  • Give yourself plenty of time to make your ORD to EYW flight. As a rule of thumb, arrive two hours before international departures and an hour ahead for domestic flights.

  • During popular months such as July, it's a good idea to get to the airport earlier than normal. Plan to arrive two hours before a domestic departure and four hours ahead for international flights when you fly during a high season in general.

  • Travelling to Key West (and then seeing more of the United States!) is a cinch with American Airlines. This popular airline offers direct flights from Chicago O'Hare International Airport to Key West International Airport.

  • The airline with the highest number of bookings on this route is American Airlines.

  • American Airlines is the most punctual carrier operating ORD to EYW flights, with 75.65% of its services landing on schedule.

  • We make it simple to book a flight with a stopover. To see all your options for tickets from Chicago O'Hare International Airport to Key West International Airport, deselect 'Direct flights only.' Then, choose a flight offering a stop long enough to explore the city of your choice. Stopovers between ORD and EYW include:

    • Atlanta Hartsfield-Jackson Airport

    • Cincinnati Northern Kentucky Airport

    • Asheville Airport

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

  • Right now, R 1,889 is the lowest price we've found for a one-way Chicago O'Hare International Airport to Key West International Airport flight. The best price for a return ticket is R 4,147. Keep in mind that fares may change due to demand at the time of booking.

  • To get cheap tickets from ORD to EYW, book your trip two months before your planned departure.

  • Schedule your trip for July. That's the cheapest month for flights from Chicago O'Hare International Airport to Key West International Airport. If you're flexible with your dates, try out the 'Whole month' tool to find the cheapest airfare across each month.

  • Stay on top of deals for cheap flights from ORD to EYW by creating a Price Alert. You'll get an email or notification on the app when a lower fare becomes available.

  • Choose your ideal departure and arrival times, airlines and number of stops with the filters. Or sort your results by 'Cheapest' to find the best deals on flights from Chicago O'Hare International Airport to Key West International Airport.

Handy information about Chicago O'Hare International Airport (ORD)

  • You'll find ORD at 10000 West O'Hare.

  • When it comes to Chicago O'Hare International Airport's on-time performance, data shows 70% of flights complete their journey on time.

  • Central Chicago to Chicago O'Hare International Airport is around 27 kilometres. Depending on traffic, it'll take you about 30 minutes to get there if you're catching a taxi, ride-sharing or driving.

  • Expect a trip time of roughly 45 minutes on public transport.

  • Get your trip off to a stress-free start by staying near ORD. Whether you're boarding an early flight from Chicago O'Hare International Airport to Key West International Airport or want to avoid feeling rushed, these stays are perfect:

Arriving at Key West International Airport (EYW)

  • The last thing you want is a lengthy journey to your hotel if you're landing late on a Chicago O'Hare International Airport to Key West International Airport flight. Stay at one of these accommodation options near EYW instead:

  • Pick up a Key West International Airport rental car and explore Key West and beyond with your own set of wheels. Dollar, Alamo and Budget are top providers you can book with here.

  • Booking your vehicle from Key West International Airport around two weeks in advance increases your chances of getting a good deal.

When to fly to Key West International Airport (EYW)

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

  • Before locking in your flight from Chicago O'Hare International Airport to Key West International Airport, consider the kind of weather you enjoy. August is the warmest month in Key West, with the temperature ranging from 26ºC (79ºF) to 30ºC (86ºF).

  • Search for cheap tickets from ORD to EYW in January if you like cooler conditions. Temperatures are at their lowest then, ranging between 18ºC (64ºF) and 23ºC (73ºF) on average.

Explore more of the United States

  • You've done Key West, now it's time to discover other corners of the United States. Travel about 209 kilometres north-east to Miami to tick off its top attractions. From Beach to Ocean Drive and Port of Miami, there's plenty to keep you busy.

  • Tampa is another sought-after destination in the United States and is around 386 kilometres north of Key West. No trip is complete without dropping by Busch Gardens Tampa, The Florida Aquarium and ZooTampa at Lowry Park.

More travel options

Prices shown on this page are estimated lowest prices only. Found in the last 12 days.