Cheap Flight Tickets from Chicago (ORD) to Key West (EYW), Starting at $206

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

$210

AA American Airlines • 1 stop • 8h 29m

Aug 26 – Aug 29

The cheapest round trip flight from Chicago to Key West (ORD-EYW-ORD) is currently $210

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Cheapest Direct Flight

$206

AA American Airlines • nonstop • 5h 19m

Aug 26

The cheapest nonstop flight from Chicago to Key West (ORD-EYW) is currently $206

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Fastest Flight

5h 19m

The fastest nonstop flight from Chicago to Key West (ORD-EYW) takes 5h 19m

Top Airlines Flying from Chicago to Key West

Delta Airline, DL

Delta Airlines

United Airlines, UA

United Airlines

American Airlines, AA

American Airlines

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.

Aug 26 - Aug 29, Economy
AA
Chicago → Key West
8h 29m
6:59 AM - 1:08 PM • 1 stop
AA
Chicago → Key West
5h 52m
4:56 PM - 7:48 PM • nonstop
$210
American Airlines
Aug 26 - Aug 29, Economy
AA
Chicago → Key West
10h 8m
6:00 AM - 1:08 PM • 1 stop
AA
Chicago → Key West
5h 52m
4:56 PM - 7:48 PM • nonstop
$210
American Airlines
Aug 26 - Aug 29, Economy
AA
Chicago → Key West
10h 50m
5:05 AM - 12:55 PM • 1 stop
AA
Chicago → Key West
5h 52m
4:56 PM - 7:48 PM • nonstop
$210
American Airlines
Aug 26 - Aug 29, Economy
AA
Chicago → Key West
12h 28m
7:30 AM - 4:18 PM • 1 stop
AA
Chicago → Key West
8h 40m
7:10 PM - 11:30 PM • 1 stop
$214
American Airlines
Aug 26 - Aug 29, Economy
DL
Chicago → Key West
9h 7m
10:33 AM - 5:20 PM • 1 stop
DL
Chicago → Key West
12h 16m
4:00 PM - 10:36 PM • 1 stop
$506
Delta Airlines
Aug 26 - Aug 29, Economy
DL
Chicago → Key West
8h 27m
1:50 PM - 7:57 PM • 1 stop
DL
Chicago → Key West
9h 15m
4:00 PM - 8:55 PM • 1 stop
$506
Delta Airlines

Fly from Chicago to Key West with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from Chicago to Key West? Find the biggest savings on one-way and round-trip tickets right here.

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 5:05 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 DL : USD 506
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 1:50 pm

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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