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 Tuesday

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

All the information you need to plan the best CHI to EYW flight in 2022: compare Chicago to Key West flight prices with the expected peak season, weather and rainfall in Key West.
CHI - EYW
Price
$345 - $524
EYW
Temperature
69.8 - 84.2 °F
EYW
Precipitation
1.5 - 6.7 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 (CHI) to Key West

One-way from

$131

One-way flight from Chicago (CHI) 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?

Monday is generally a great day to depart. Flying on this day could help you save up to 27%.

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

Our data shows that August tends to be the cheapest month to fly to Key West from Chicago. Users have commonly found prices around $428 for the month, but tickets can be as low as $253. Due to multiple factors, prepare for potentially higher prices in December.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 57 days in advance, which can save you up to 42% on flights from Chicago to Key West compared to booking the week you need them. Waiting 57 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $480. For sooner than that we have options available in the next 3 days from $649.

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

It’s optimal to fly from Chicago to Key West in the evening. By choosing this option you can save up to 55% on the cost of your flight, compared to a flight in the morning.

Cheap flights from Chicago to Key West in January, February 2022

The best prices found for CHI to EYW flights for January, February
28 Jan - 2 Feb
$147pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
8 Feb - 16 Feb
$153pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
1 Feb - 3 Feb
$159pp
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 2022 flight deals

Cheap flights to Key West from Chicago found for this year
28 Jan - 2 Feb
$147pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
8 Feb - 16 Feb
$153pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
1 Feb - 3 Feb
$159pp
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
22 Feb - 3 Mar
$218pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
20 Feb - 3 Mar
$238pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
2 Mar - 10 Mar
$248pp
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
28 Jan - 2 Feb
$147pp
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 Jan - 2 Feb
$173pp
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
27 Jan - 3 Feb
$182pp
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
12:20 pm - 8:28 am
American Airlines
1 Stop
19h 08m
ORD - EYW
American Airlines
7:38 am - 9:20 am
Multiple Airlines
1 Stop
24h 42m
ORD - EYW
Multiple Airlines
$139
Kiwi.com
3:55 am - 3:37 pm
United Airlines
1 Stop
10h 42m
ORD - EYW
United Airlines
$146
United

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Chicago</span> to <span class="emphasized">Key West</span> flights.

Flight FAQs

From Chicago to Key West

What airport do you fly into for flights to Key West from Chicago?

Located just 2.6 mi from the city center, Key West is the airport most travelers will use when flying to Key West from Chicago. Booking flights from Chicago to Key West (EYW) should be relatively easy as there are 2 daily inbound flights from Chicago from 4 different airlines.

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 $147, but on average you can expect to pay $181.

Are there nonstop flights from Chicago to Key West for under $300 on Cheapflights?

Cheapflights has at least 20 direct flights from Chicago to Key West under $300. A good price for a nonstop flight from Chicago to Key West is less than $303.

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 are the most popular airlines that fly from Chicago to Key West?

The most popular airlines flying from Chicago to Key West are American Airlines, JetBlue and Delta. Something to consider prior to booking your flight.

What are the cheapest flights from Chicago to Key West?

Looking for the cheapest flight from Chicago to Key West? While on average our users pay $624, our data indicates the cheapest price to be $199. The most popular route (Chicago O'Hare Intl - Key West), is priced around $159.

COVID Restrictions

View COVID Travel Restrictions for Key West, FL

Do I need a COVID test to fly to Key West from Chicago?

Information is based on travel restrictions for travel to Key West within the United States

Most visitors from Chicago need to provide a negative COVID-19 test result and/or quarantine to enter Key West.

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Key West.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Key West.

Do I need a test to fly back to Chicago from Key West?

Returning to Chicago from Key West

COVID-19 testing requirements
Visitors from Key West must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 24 hours before departing to Chicago.

Quarantine requirements
Visitors from Key West are not required to quarantine after entering Chicago.

Hide COVID Travel Restrictions for Key West, FL

Alternative routes for Chicago to Key West

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Key West

Things to know before you go - useful duration and weather info for your trip from Chicago to Key West.
Flight duration from Chicago to EYW
3h 19m
Average temperature for January in Key West
77.0 °F
Avg rainfall for January in Key West
1.8 ″

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Airports servicing Key West

Top 4 airlines flying 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

See what time of day planes typically take off from Chicago towards 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
See how many times per day planes take to the skies headed from Chicago to Key West.
Sunday
1 daily flight
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
2 daily flights
Saturday
3 daily flights
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