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 2021: 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
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

$149

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 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 $452 on average during August, but can be found for as low as $217.

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 55% on the flight price compared to flying in the morning, which is usually more expensive.

Cheap flights from Chicago to Key West in July, August 2021

The best prices found for CHI to EYW flights for July, August
12 Aug - 18 Aug
$215pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 Aug - 1 Sep
$233pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
12 Aug - 18 Aug
$236pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Chicago to Key West 2021 flight deals

Cheap flights to Key West from Chicago found for this year
12 Aug - 18 Aug
$215pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
29 Aug - 1 Sep
$233pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
12 Aug - 18 Aug
$236pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl

Non-stop flights to Key West from Chicago

Save time with Chicago to Key West direct flight deals
22 Oct - 24 Oct
$369pp
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EYW
Key West
EYW
Key West
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
25 Oct - 29 Oct
$377pp
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
12 Aug - 16 Aug
$379pp
ORD
Chicago O'Hare Intl
United 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
31 Jul - 3 Aug
$274pp
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
31 Jul - 3 Aug
$278pp
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
EYW
Key West
EYW
Key West
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
31 Jul - 3 Aug
$282pp
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
EYW
Key West
EYW
Key West
American 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
9:40 am - 11:30 am
Allegiant Air
2 Stops
24h 50m
MDW - EYW
Allegiant Air
$149
Gotogate
2:15 pm - 12:35 pm
United Airlines
1 Stop
21h 20m
ORD - EYW
United Airlines
$177
United
6:15 am - 2:29 pm
Delta
1 Stop
7h 14m
MDW - EYW
Delta
$219
Delta

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

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.

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.

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 3 daily inbound flights from Chicago from 4 different airlines.

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 $215, but on average you can expect to pay $262.

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

Cheapflights has at least 20 direct flights from Chicago to Key West under $400. A good price for a nonstop flight from Chicago to Key West is less than $424.

Are there last-minute flights available from Chicago to Key West for under $300?

There are currently 20+ open flights from Chicago to Key West within the next 7 days for less than $300.

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

Days when nonstop flights are available for this flight are: Tuesday.

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

Travelers can expect 2 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 45m. Delta provides one of the quickest options available for as low as $597. The distance from Chicago to Key West is about 1261 mi.

What are the cheapest airlines flying from Chicago to Key West round-trip?

Currently priced at $245, American Airlines will fly you from Chicago to Key West and back. In addition to American Airlines, many other airlines offer competitively priced options for your trip. Check Cheapflights for deals on United Airlines for as low as $277. Users have found that American Airlines is 42% cheaper than the other options available to this destination.

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

The cheapest airlines for a one-way flight from Chicago to Key West are American Airlines ($128), United Airlines ($144), and Allegiant Air ($149).

COVID Restrictions

View COVID Travel Restrictions for Key West, FL

Can I fly to Key West from Chicago right now?

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 72 hours before departing to Key West.

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

Can I 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 72 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.
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

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
4 daily flights
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
4 daily flights
Friday
4 daily flights
Saturday
4 daily flights
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