Cheap flights from Chicago (CHI) to Key West (EYW)
The best prices from Chicago to Key West are usually found in January or September, booked 60 days in advance, depart on a Wednesday or Tuesday and return on a Friday
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 | $409 - $537 |
|---|---|
EYW Temperature | 69.8 - 84.2 °F |
EYW Rainfall | 1.5 - 6.7 inches |
| Popular in | March | High demand for flights, 13% potential price rise |
|---|---|---|
| Cheapest in | January | Best time to find cheap flights, 12% potential price drop |
| Round-trip from | $409 | From Chicago (CHI) to Key West |
| One-way from | $101 | One-way flight from Chicago (CHI) to Key West |
What is the cheapest day to fly round-trip from Chicago to Key West?
Tuesday is generally a great day to depart. Flying on this day could help you save up to 26%.
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 61 days in advance, which can save you up to 39% on flights from Chicago to Key West compared to booking the week you need them. Waiting 61 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 $567. For sooner than that we have options available in the next 3 days from $685.
What is the cheapest month to fly from Chicago to Key West?
Our data shows that January tends to be the cheapest month to fly to Key West from Chicago. Users have commonly found prices around $467 for the month, but tickets can be as low as $277. Due to multiple factors, prepare for potentially higher prices in March.
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 19% on the cost of your flight, compared to a flight in the morning.
Cheap flights from Chicago to Key West in November, December 2022
The best prices found for CHI to EYW flights for November, December
Chicago Midway
Key West
2 stops
18h 22mKey West
Chicago Midway
1 stop
9h 07mMultiple Airlines
Chicago Midway
Key West
2 stops
18h 35mKey West
Chicago Midway
1 stop
27h 15mAllegiant Air
Chicago Midway
Key West
1 stop
26h 04mKey West
Chicago Midway
1 stop
8h 53mMultiple Airlines
Chicago to Key West 2022 flight deals
Cheap flights to Key West from Chicago found for this year
Chicago Midway
Key West
2 stops
18h 22mKey West
Chicago Midway
1 stop
9h 07mMultiple Airlines
Chicago Midway
Key West
2 stops
18h 35mKey West
Chicago Midway
1 stop
27h 15mAllegiant Air
Chicago Midway
Key West
1 stop
26h 04mKey West
Chicago Midway
1 stop
8h 53mMultiple Airlines
Cheap American Airlines flights from Chicago to Key West
Chicago O'Hare Intl
Key West
Nonstop
3h 48mKey West
Chicago O'Hare Intl
Nonstop
3h 30mAmerican Airlines
Chicago O'Hare Intl
Key West
1 stop
7h 07mKey West
Chicago O'Hare Intl
Nonstop
3h 30mAmerican Airlines
Chicago O'Hare Intl
Key West
1 stop
6h 48mKey West
Chicago O'Hare Intl
1 stop
5h 30mAmerican Airlines
Cheap United Airlines flights from Chicago to Key West
Chicago O'Hare Intl
Key West
Nonstop
3h 22mKey West
Chicago O'Hare Intl
1 stop
6h 50mUnited Airlines
Chicago O'Hare Intl
Key West
1 stop
6h 54mKey West
Chicago O'Hare Intl
1 stop
7h 00mUnited Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 22mKey West
Chicago O'Hare Intl
Nonstop
3h 33mUnited Airlines
Non-stop flights to Key West from Chicago
Save time with Chicago to Key West direct flight deals
Chicago O'Hare Intl
Key West
Nonstop
3h 48mKey West
Chicago O'Hare Intl
Nonstop
3h 30mAmerican Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 22mKey West
Chicago O'Hare Intl
Nonstop
3h 33mUnited Airlines
Chicago O'Hare Intl
Key West
Nonstop
3h 25mKey West
Chicago O'Hare Intl
Nonstop
3h 33mUnited Airlines
Last minute flights from Chicago to Key West
Late deals on return flights to Key West from Chicago, departing today and this week
Chicago Midway
Key West
1 stop
7h 20mKey West
Chicago Midway
1 stop
27h 19mMultiple Airlines
Chicago Midway
Key West
2 stops
17h 28mKey West
Chicago Midway
1 stop
15h 06mMultiple Airlines
Chicago O'Hare Intl
Key West
1 stop
6h 14mKey West
Chicago O'Hare Intl
Nonstop
3h 27mUnited Airlines
One-way flights to Key West from Chicago
The cheapest one-way flights from Chicago to Key West
Chicago O'Hare Intl
Key West
2 stops
26h 31mMultiple Airlines
Chicago O'Hare Intl
Key West
1 stop
14h 08mMultiple Airlines
Chicago Midway
Key West
2 stops
25h 26mMultiple Airlines
Related info for your journey
Useful info, stats and facts about Chicago to Key West flights.
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 0 daily inbound flights from Chicago from 6 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 $192, but on average you can expect to pay $250.
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 $379.
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?
Nonstop flights are available for this route on the following days: Tuesday, Wednesday, Thursday, Friday.
How many flights depart from Chicago to Key West on average per day?
4 flight departures from Chicago to Key West per day on average.
Morning (6am - Noon) - 100% of flight departures
How long is the flight from Chicago to Key West?
Airlines like American Airlines, United Airlines, and Delta fly from Chicago to Key West in about 3h 22m. The time it takes to get you to your destination can typically vary by up to 5h 31m. Chicago and Key West are separated by a distance of 1261 mi. Both multi-stop and nonstop flights can be found to your destination and back.
What are the cheapest airlines flying from Chicago to Key West round-trip?
Our cheapest airline available from Chicago to Key West is American Airlines. Our recent data shows that you can find tickets from as low as $248 on this airline. Additional options worth looking into are United Airlines and Delta, starting at $257 and $270 round-trip. American Airlines is currently priced 46% below the average price you’ll pay for this route.
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, Alaska Airlines 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 $1,249, our data indicates the cheapest price to be $226. The most popular route (Chicago O'Hare Intl - Key West), is priced around $245.
Other flights from Chicago
Flights to Key West from Chicago
Alternative routes for Chicago to Key West
See prices for flight routes from nearby airports that may be better suited for you.
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.
Hourly flight availability from Chicago to Key West
See what time of day planes typically take off from Chicago to Key West
| 0%of flight departures | Early morningMidnight to 6 am |
|---|---|
| 100%of flight departures | Morning6 am to noon |
| 0%of flight departures | AfternoonNoon to 6 pm |
| 0%of flight departures | Evening6 pm to midnight |
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 | 1daily flight |
|---|---|
| Monday | 1daily flight |
| Tuesday | 1daily flight |
| Wednesday | 0daily flights |
| Thursday | 0daily flights |
| Friday | 0daily flights |
| Saturday | 1daily flight |