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

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

How to find the cheapest flight from
Chicago (CHI) to Key West (EYW)

CHI - EYW
Price
$368 - $524
EYW
Temperature
77 - 91.4 °F
EYW
Rainfall
1.1 - 6.6 inches
Popular in December High demand for flights, 15% potential price rise
Cheapest in September Best time to find cheap flights, 17% potential price drop
Round-trip from $368 From Chicago to Key West
One-way from $116 One-way flight from Chicago to Key West
Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Chicago to Key West?

Flying to your destination on a Wednesday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Key West. Check prices with Cheapflights to find a great deal for your trip.

What is the cheapest month to fly from Chicago to Key West?

Due to multiple factors, expect to potentially pay more when booking in March. For low rates, September can be a great choice for travel to Key West. Flights to Key West from Chicago in September are about $478 on average during September, but can be found for as low as $175.

Cheap flights from Chicago to Key West in July, August 2020

The best prices found for CHI to EYW flights for July, August
15 Jul - 20 Jul
$216pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
13 Jul - 16 Jul
$225pp
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 Jul - 5 Aug
$226pp
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
4 Aug - 10 Aug
$209pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
11 Aug - 18 Aug
$213pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
15 Jul - 20 Jul
$216pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl

Non-stop flights to Key West from Chicago

Save time with Chicago to Key West direct flight deals
14 Nov - 20 Nov
$399pp
ORD
Chicago O'Hare Intl
Cape Air
Non-Stop
EYW
Key West
EYW
Key West
Cape Air
Non-Stop
ORD
Chicago O'Hare Intl
11 Jul - 18 Jul
$453pp
ORD
Chicago O'Hare Intl
Sun Country Air
Non-Stop
EYW
Key West
EYW
Key West
Sun Country Air
Non-Stop
ORD
Chicago O'Hare Intl
25 Nov - 21 Mar
$586pp
ORD
Chicago O'Hare Intl
Multiple Airlines
Non-Stop
EYW
Key West
EYW
Key West
United Airlines
Non-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
28 Jun - 10 Jul
$315pp
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 Jun - 3 Jul
$317pp
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 Jun - 7 Jul
$318pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
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
1:09 am - 7:40 am
JetBlue
1 Stop
5h 31m
ORD - EYW
JetBlue
4:54 am - 6:29 pm
Allegiant Air
2 Stops
12h 35m
ORD - EYW
Allegiant Air
$217
Ovago
5:19 am - 1:40 pm
Silver Airways
1 Stop
7h 21m
ORD - EYW
Silver Airways
$288
Ovago

Related info for your journey

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

Flight FAQs

From Chicago to Key West

Are flight prices decreasing from Chicago to Key West due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Chicago and Key West for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

Can I find flights from Chicago to Key West for under $300 on Cheapflights?

Yes, there are multiple flights from Chicago to Key West for under $300. The cheapest flight booked recently is on Multiple Airlines for just $209, but on average you can expect to pay $228.

Are there nonstop flights from Chicago to Key West for under $400 on Cheapflights?

Cheapflights has at least 4 direct flights from Chicago to Key West under $400. A good price for a nonstop flight from Chicago to Key West is less than $1098.

Are there last-minute flights available from Chicago to Key West for under $400?

There are currently 20+ open flights from Chicago to Key West within the next 7 days for less than $400.

How popular is this flight route?

Flights from Chicago to Key West have been viewed 27 times in the past calendar month.

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.

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.

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 July in Key West
89.6 °F
Avg rainfall for July in Key West
3.8 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Key West

Hourly flight availability from Chicago to Key West

Morning 6 AM to noon 100% of CHI to EYW departures
Early morning Midnight to 6 AM 0% of CHI to EYW departures
Afternoon Noon to 6 PM 0% of CHI to EYW departures
Evening 6 PM to midnight 0% of CHI to EYW departures
Midnight
6 AM
Noon
6 PM