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Uncover the best deals on Chicago to Key West flights by comparing fares from hundreds of airlines and agencies.
Good to Know: Cheapest and Fastest ORD - EYW Flights
Useful information for finding best airline tickets from Chicago O'Hare International to Key West International on your next trip.
Cheapest Round Trip Flight
$223
American Airlines
• 1 stop
• 10h 1m
Dec 09 – Dec 13
The cheapest round trip flight from Chicago to Key West (ORD-EYW-ORD) is currently $223
Cheapest Direct Flight
$218
American Airlines
• nonstop
• 5h 32m
Dec 09
The cheapest nonstop flight from Chicago to Key West (ORD-EYW) is currently $218
Fastest Flight
5h 31m
The fastest nonstop flight from Chicago to Key West (ORD-EYW) takes 5h 31m
Top Airlines Flying from Chicago to Key West
Latest Flight Deals from Chicago (ORD) to Key West (EYW)
Compare and book low fare round-trip air tickets from Chicago to Key West. Ideal for travelers with confirmed return itineraries.
Dec 09 - Dec 13, Economy
Chicago → Key West
10h 1m
8:10 AM - 3:11 PM • 1 stop
Chicago → Key West
5h 49m
1:01 PM - 3:50 PM • nonstop
American Airlines
Dec 09 - Dec 13, Economy
Chicago → Key West
10h 43m
5:23 AM - 1:06 PM • 1 stop
Chicago → Key West
5h 49m
1:01 PM - 3:50 PM • nonstop
American Airlines
Dec 09 - Dec 13, Economy
Chicago → Key West
13h 24m
8:15 AM - 5:19 PM • 1 stop
Chicago → Key West
13h 38m
4:41 PM - 11:59 PM • 2 stops
American Airlines
Dec 09 - Dec 13, Economy
Chicago → Key West
10h 7m
10:12 AM - 5:19 PM • 1 stop
Chicago → Key West
13h 38m
4:41 PM - 11:59 PM • 2 stops
American Airlines
Dec 09 - Dec 13, Economy
Chicago → Key West
10h 43m
5:23 AM - 1:06 PM • 1 stop
Chicago → Key West
15h 28m
2:36 PM - 11:04 PM • 1 stop
American Airlines
Looking for the fastest way to Key West? These direct flight options from ORD to EYW offer both convenience and value—no layovers, just straight to your destination.
FAQs on Chicago to Key West Flights
What are the airports in Chicago?
MDW,ORD
What’s the most popular airline flying from ORD to EYW?
The most popular airline flying from Chicago to Key West are
Can I fly from ORD to EYW non-stop?
Yes, you can fly ORD to EYW non-stop on
Which airlines fly nonstop between Chicago and Key West?
The non-stop flights between Chicago and Key West are .
What’s the earliest departure time from ORD to EYW Airport?
The earliest flight leaves ORD at 5:23 am and lands in EYW - Key West International
What are the airports in Key West?
EYW
Can I make changes to my Chicago to Key West flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from ORD to EYW?
Read the fare rules of the Chicago to Key West air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from Chicago and Key West?
operate flights between Chicago and Key West
How long does a flight from Chicago to Key West take?
It takes approximately 3 hour to fly non-stop from ORD to EYW, which is 1251.41 miles by air.
Which airlines provide the cheapest flights from Chicago (ORD) to Key West (EYW) ?
In the past couple of days, the cheapest tickets to EYW from ORD were found on AA : USD 584
Do I need a passport to fly between ORD and EYW?
No
What’s the latest departure time from ORD to EYW ?
The last flight leaves ORD at 10:55 am
Chicago (ORD) to Key West (EYW): Airport Information
| Origin Airport | Chicago O'Hare International , Chicago, US |
| Destination Airport | Key West International , Key West, US |
| Distance | 1251 miles |
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