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C$153 Cheap Flights from Chicago O'Hare International (ORD) to Key West International (EYW)

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

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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 C$497. Find the lowest prices on one-way and return tickets right here.
Key West.C$153 per passenger.Departing Wed., Jul. 8.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed., Jul. 8, arriving in Key West International.Price includes taxes and charges.From C$153, select.
Key West.C$184 per passenger.Departing Mon., Nov. 2.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Mon., Nov. 2, arriving in Key West International.Price includes taxes and charges.From C$184, select.
Key West.C$185 per passenger.Departing Wed., Sep. 30.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Wed., Sep. 30, arriving in Key West International.Price includes taxes and charges.From C$185, select.
Key West.C$195 per passenger.Departing Thu., Aug. 13.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Thu., Aug. 13, arriving in Key West International.Price includes taxes and charges.From C$195, select.
Key West.C$287 per passenger.Departing Fri., May 29.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Fri., May 29, arriving in Key West International.Price includes taxes and charges.From C$287, select.
Key West.C$289 per passenger.Departing Sat., Jun. 13.One-way flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Chicago O'Hare International on Sat., Jun. 13, arriving in Key West International.Price includes taxes and charges.From C$289, select.
Key West.C$390 per passenger.Departing Sun., Jun. 28.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sun., Jun. 28, arriving in Key West International.Price includes taxes and charges.From C$390, select.
Key West.C$391 per passenger.Departing Mon., Nov. 2.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Mon., Nov. 2, arriving in Key West International.Price includes taxes and charges.From C$391, select.
Key West.C$391 per passenger.Departing Wed., Jul. 8.One-way flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Wed., Jul. 8, arriving in Key West International.Price includes taxes and charges.From C$391, select.
Key West.C$391 per passenger.Departing Fri., Jan. 1.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri., Jan. 1, arriving in Key West International.Price includes taxes and charges.From C$391, select.
Key West.C$392 per passenger.Departing Tue., Dec. 15.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue., Dec. 15, arriving in Key West International.Price includes taxes and charges.From C$392, select.
Key West.C$393 per passenger.Departing Sat., Oct. 10.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat., Oct. 10, arriving in Key West International.Price includes taxes and charges.From C$393, select.
Key West.C$393 per passenger.Departing Thu., Aug. 6.One-way flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu., Aug. 6, arriving in Key West International.Price includes taxes and charges.From C$393, 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 July.
May
from C$287
Jun.
from C$289
Jul.
from C$153
Aug.
from C$195
Sep.
from C$185
Oct.
from C$393
Nov.
from C$184
Dec.
from C$392
Jan.
from C$391
Feb.
Find prices
Mar.
Find prices
Apr.
Find prices

Which airlines fly 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 C$153
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Chicago to Key West: Flight information

The things to know before you go.
Cheapest flight foundC$153
Cheapest month to flyJuly
Average flight time3 hrs, 23 mins
Most popular airlineEnvoy Air
Average flights per week56

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 C$384. 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 23 minutes is the average flight time from Chicago O'Hare International to Key West International.
Envoy Air, American Airlines and United fly direct from Chicago O'Hare International to Key West International.
As of May 2026, there are 56 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 August.
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 Thursday, August 20, 2026.
Yes – the average flight time is 3 hours and 23 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 United offer the cheapest flight tickets to Key West International.

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

  • Longer lines at security and check-in are likely if you're traveling during high season, so allow even more breathing space. A good rule of thumb for peak periods? Arrive up to four hours ahead for international flights and two hours for domestic departures.

  • We make it a cinch to book a flight with a stopover. To look at the options for flights from 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. Popular stopovers between ORD and EYW are:

    • Cincinnati/Northern Kentucky Airport

    • Hartsfield-Jackson Atlanta International Airport

    • Asheville Regional Airport

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

  • C$153 is currently the best price for a one-way ticket from O'Hare International Airport to Key West International Airport. Return flights start at C$384. These prices can change depending on demand.

  • It's usually best to book in advance if you're looking for cheap flight tickets from ORD to EYW. That's because airlines adjust prices based on demand, which tends to rise closer to the date of departure.

  • Getting cheap flight tickets from O'Hare International Airport to Key West International Airport is easy if you can be flexible with your travel dates. Try using the 'Whole month' search tool to see the lowest prices across the month and score a great deal.

  • Finding a cheap ticket from ORD to EYW couldn't be easier with Price Alerts. Simply set up one of these automatic alerts and we'll get in touch when the price has fallen.

  • Take advantage of filters to find the ideal journey for you. To see the 'Fastest,' 'Best' or 'Cheapest' flights from O'Hare International Airport to Key West International Airport, use the 'Sort by' function. You can also filter by airline, departure and arrival times, and journey duration.

Handy information about O'Hare International Airport (ORD)

Arriving at Key West International Airport (EYW)

  • The last thing you want is a long journey to your hotel if you're getting in late on a flight from O'Hare International Airport to Key West International Airport. Check in to one of these accommodation options near EYW instead:

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

  • Key West International Airport to the center of Key West is about 6 minutes in a car. It's approximately 3 kilometres away. Find out what options are available, such as car rentals, cabs or ride-sharing services.

  • It typically takes 40 minutes to get there using public transport.

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 July is the busiest. Pick the best 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 O'Hare International Airport to Key West International Airport, think about the type of weather you enjoy. August is the warmest month in Key West, with the temperature ranging from 26ºC to 30ºC.

  • January has average temperatures of between 18ºC and 23ºC. Search for cheap flight tickets from ORD to EYW around that time if you want to travel when it's cooler.

More about Key West

  • After booking your flights from ORD to EYW, you'll want to find somewhere to stay in Key West. Make one of these options your base for exploring this exciting city:

  • Every great vacation has to include some sightseeing. Mallory Square, The Ernest Hemingway Home and Museum and Fort Zachary Taylor Historic State Park are must-have experiences during your Key West visit.

Complete your Key West trip with hotels and a car rental

  • Comparing flights is not the only thing we do. Once you've secured your cheap ticket to Key West International Airport, check out our car rental offers that'll give you the flexibility and freedom to travel around at your own pace. Then, take a look at our exclusive rates for hotels to find your ideal Key West stay.

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