Menu

Cheap flights from Chicago to Key West (CHI - EYW)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Chicago to Key West are usually found in September or August, booked 60 days in advance, depart on a Tuesday or Monday and return on a Wednesday

$590
$520
$440
$368
(CHI - EYW)
Price
$368 - $524
EYW
Temperature
77 - 91 °F
EYW
Rainfall
1 - 7 inches
Most popular in December High demand for flights, 6% potential price rise
Cheapest in September Best time to find cheap flights, 2% potential price drop
Average price $468 Price for this month
Cheapest price $368 From Chicago to Key West

Cheap flights from Chicago to Key West in March 2020

The best prices found for ORD to EYW flights for March
9 Mar - 17 Mar
$269pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
28 Mar - 31 Mar
$276pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
25 Mar - 1 Apr
$280pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Chicago to Key West 2020 flight deals

Cheap flights to Key West from Chicago found for this year
31 Mar - 7 Apr
$218pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
18 Apr - 21 Apr
$237pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
21 Apr - 25 Apr
$242pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Last minute flights from Chicago to Key West

Late deals on round-trip flights to Key West from Chicago, departing today and this week
2 Mar - 5 Mar
$336pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
3 Mar - 18 Mar
$345pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
4 Mar - 10 Mar
$377pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

One-way flights to Key West from Chicago

The cheapest one-way flights from Chicago to Key West
4:28 am - 8:47 am
Major Airline
Nonstop
3h 19m
ORD - EYW
Major Airline
$369
StudentUniverse
6:25 am - 10:44 am
United Airlines
Nonstop
3h 19m
ORD - EYW
United Airlines
$780
United
4:28 am - 8:47 am
American Airlines
Nonstop
3h 19m
ORD - EYW
American Airlines

Alternative routes for Chicago to Key West

Destination information for Key West

Things to know before you go. Useful info for your trip from Chicago to Key West
Average temperature for February in Key West
78.8 °F
Avg rainfall for February in Key West
1.1 ″

Airports servicing Chicago

Chicago-O'Hare Intl (ORD)
Rockford (RFD)

Airports servicing Key West

Weekly flight availability
from Chicago to Key West
Sunday
3 daily flights
Monday
4 daily flights
Tuesday
3 daily flights
Wednesday
3 daily flights
Thursday
4 daily flights
Friday
3 daily flights
Saturday
4 daily flights

Related info for your journey

Useful info, stats and facts about Chicago to Key West flights.

Flight FAQs

From Chicago to Key West

What days are nonstop flights available from Chicago to Key West?

Days when nonstop flights are available for this flight are: Sunday, Monday, Tuesday, Wednesday, Thursday, Friday, Saturday.

How popular is this flight route?

Flights from Chicago to Key West have been viewed 22 times in the past calendar month.

What percent of flights are delayed?

Airlines departing from Chicago to Key West are usually on time.

How many passenger seats are available on a flight on this route?

78,254,530 passengers can be comfortably seated on when flying from Chicago to Key West on average per day.

What is the cheapest airline for this route?

While browsing flights check up on current rates for Delta Air Lines, Inc.. Delta Air Lines, Inc. offers the cheapest flight to Chicago to Key West. Flight availability can sometimes range however expect there to be 273 flights on average per day.

How long does the flight from Chicago to Key West take?

A nonstop flight takes up to 4 hours, covering a distance of 784 miles.

How many flights depart from Chicago to Key West on average per day?

Travelers can expect 7 flights from Chicago to Key West on average per day.
Morning (6am - Noon) - 86% of flight departures
Evening (6pm - Midnight) - 14% of flight departures

Is Chicago weather warmer or cooler than Key West?

Temperatures around the 91 °F's can be experienced in August. The weather in Key West is hotter than in Chicago. Plan for potential changes in flight availability as peak weather approaches in this location.