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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 August or September, booked 57 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
$345 - $524
EYW
Temperature
77 - 91.4 °F
EYW
Rainfall
1.1 - 6.6 inches

Popular in

December

High demand for flights, 18% potential price rise

Cheapest in

August

Best time to find cheap flights, 19% potential price drop

Round-trip from

$345

From Chicago to Key West

One-way from

$74

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.

How far in advance should I book a flight from Chicago to Key West?

To save on the cost of your flight from Chicago to Key West, book at least 37 days before your planned departure. Booking around this time can save you about 40% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $480 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $607.

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

Due to multiple factors, expect to potentially pay more when booking in December. For low rates, August can be a great choice for travel to Key West. Flights to Key West from Chicago in August are about $413 on average during August, but can be found for as low as $181.

When is the cheapest time to fly from Chicago to Key West (CHI - EYW)?

It’s typically best to fly out from Chicago to Key West in the evening. Doing so could potentially save you 43% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Chicago to Key West in November, December 2020

The best prices found for CHI to EYW flights for November, December
13 Dec - 26 Dec
$171pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
17 Dec - 23 Dec
$184pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
30 Nov - 4 Dec
$190pp
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 2021 flight deals

Cheap flights to Key West from Chicago found for next year
13 Dec - 26 Dec
$171pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
17 Dec - 23 Dec
$184pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
30 Nov - 4 Dec
$190pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
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
18 Dec - 21 Dec
$479pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
11 Dec - 15 Dec
$483pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EYW
Key West
EYW
Key West
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
7 Dec - 12 Dec
$487pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
EYW
Key West
American 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
30 Nov - 4 Dec
$190pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
30 Nov - 4 Dec
$212pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
29 Nov - 30 Nov
$228pp
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
12:15 am - 9:50 am
Multiple Airlines
1 Stop
8h 35m
ORD - EYW
Multiple Airlines
$74
Gotogate
4:18 am - 12:25 pm
Multiple Airlines
1 Stop
7h 07m
ORD - EYW
Multiple Airlines
$88
Gotogate
12:10 am - 12:25 pm
Multiple Airlines
1 Stop
11h 15m
ORD - EYW
Multiple Airlines
$96
FlyFar

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.

What safety measures are being taken by airlines flying from Chicago to Key West to control the spread of COVID-19?

Airlines globally have implemented additional safety measures to accommodate you. JetBlue and Delta are some airlines that have done so. New policies for travelers booking flights from Chicago to Key West include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Chicago to Key West have flexible cancellations due to COVID-19?

Some of the carriers operating flights from Chicago to Key West that may be offering flexible cancellation policies are American Airlines, United Airlines, and Delta. Our site will let you filter for all airlines offering greater flexibility due to COVID-19.

Can I find flights from Chicago to Key West for under $200 on Cheapflights?

Yes, there are multiple flights from Chicago to Key West for under $200. The cheapest flight booked recently is on Multiple Airlines for just $141, but on average you can expect to pay $169.

Are there nonstop flights from Chicago to Key West for under $500 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Key West under $500. A good price for a nonstop flight from Chicago to Key West is less than $544.

Are there last-minute flights available from Chicago to Key West for under $200?

There are currently 20+ open flights from Chicago to Key West within the next 7 days for less than $200.

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

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

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

Travelers can expect 4 flights from Chicago to Key West on average per day.
Morning (6am - Noon) - 100% 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.

How long is the flight from Chicago to Key West?

A quick flight from Chicago to Key West can take about 4h 34m. Delta provides one of the quickest options available for as low as $606. The distance from Chicago to Key West is about 1261 mi.

What are the cheapest airlines to fly from Chicago to Key West one-way?

The cheapest airline for a one-way flight from Chicago to Key West is American Airlines ($134).

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 November in Key West
80.6 °F
Avg rainfall for November in Key West
1.9 ″

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Airports servicing Key West

Top 4 airlines from Chicago to Key West

The chart below displays the airlines Cheapflights users traveling from Chicago to Key West choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
JetBlue
$148 $210 No cancel fee 62%
American Airlines
$185 $423 No cancel fee 71%
Delta
$222 $517 No cancel fee N/A
United Airlines
$223 $563 No cancel fee 69%

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