Cheap flights from Chicago (CHI) to Key West (EYW) from $109
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
The best prices from Chicago to Key West are usually found in August or January, booked 60 days in advance, depart on a Tuesday or Wednesday and return on a Monday
Cheap flight deals from Chicago to Key West
Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Key West (EYW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated May 4, 2024.
Popular in | March |
|---|---|
Cheapest in | August |
Round-trip from | $374 |
One-way from | $216 |
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 35%.
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 53% 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 $347. For sooner than that we have options available in the next 3 days from $347.
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 $451 for the month, but tickets can be as low as $226. 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 at noon. By choosing this option you can save up to 37% on the cost of your flight, compared to a flight in the evening.
Cheap Delta flights from Chicago to Key West
Explore cheap flight options specifically provided by Delta for the route between Chicago and Key West. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Find some of the cheapest Delta flights traveling from Chicago to Key West. Deals update often to give you more flight options matching your criteria
Cheap American Airlines flights from Chicago to Key West
Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Key West. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Take a gander at the lowest prices we've found on American Airlines flights from Chicago to Key West. Check back soon if you're not seeing flights that suit your needs.
Cheap Chicago to Key West flights in May & June 2024
Find cheap flight options from Chicago to Key West specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Prices were last updated on May 4, 2024.
These are some of the most attractive deals on flights from Chicago to Key West in 2024. Check back soon for alternative fares.
Chicago to Key West 2024 flight deals
Discover exclusive flight deals for travel between Chicago and Key West in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
These are some of the most attractive deals on flights from Chicago to Key West in 2024. Check back soon for alternative fares.
Chicago to Key West flights leaving soon
Find last-minute flight options from Chicago to Key West for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Check out these flights departing soon from Chicago to Key West. Users should double check the flight they book to ensure it matches the day, time, and destination they're looking for.
One-way flights to Key West from Chicago
Search for one-way flight options from Chicago to Key West. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Take a look at some of the best available options we've come across on one-way flights from Chicago to Key West. For those needing a return trip from Chicago, there is a search form available above.
Find flights from Chicago to Key West within your budget
Customize your flight search to find flights from Chicago to Key West that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Fly from
Fly to
Budget
$216 - $453
Route
Depart
Return
Price
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 9/4
1 stop5h 58m
Key West
Tue 9/10
1 stop4h 39m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 9/4
1 stop5h 58m
Key West
Tue 9/10
1 stop4h 39m
Chicago MidwayKey West
MDW - EYW
MDWEYW
Chicago Midway
Wed 9/11
1 stop5h 28m
Key West
Tue 9/17
1 stop4h 39m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Fri 6/14
1 stop6h 18m
Key West
Mon 6/17
1 stop5h 10m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 5/29
1 stop6h 38m
Key West
Wed 6/5
1 stop5h 59m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sat 5/25
1 stop6h 38m
Key West
Tue 5/28
1 stop6h 25m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Wed 5/29
2 stops6h 48m
Key West
Wed 6/5
1 stop7h 44m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Thu 6/6
1 stop11h 58m
Key West
Sun 6/9
2 stops24h 19m
Chicago O'Hare IntlKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
Sat 5/11
1 stop26h 57m
Key West
Tue 5/14
2 stops12h 00m
When is the best time to book a flight from Chicago to Key West?
Use this chart to determine the optimal time to book a round-trip flight from Chicago to Key West. Price data was last updated on May 3, 2024.
The best time to book flights from Chicago to Key West is 60 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
When is the cheapest time to fly from Chicago to Key West?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Key West. Price data was last updated on April 28, 2024.
Average price of flights to Key West by month
Plan your trip from Chicago to Key West by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Key West is currently $212 while a round-trip flight costs $286. Price data was last updated on April 28, 2024.
Currently, January is the cheapest month in which you can book a flight from Chicago to Key West (average of $374). Flying from Chicago to Key West in March is currently the most expensive (average of $504). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
January
$374
February
$414
March
$504
April
$481
May
$472
June
$479
July
$451
August
$382
September
$407
October
$468
November
$450
December
$399
Temperature and rainfall in Key West by month
Plan your trip to Key West by taking into account the average temperature and rainfall totals by month.
EYW Temperature | 69.8 - 84.2 °F |
|---|
Reviews of airlines servicing Key West
Get insights into the airlines that provide service to Key West. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Key West. Reviews last updated May 4, 2024.
To help decide which airline to fly from Chicago to Key West, see what other customers have to say about Delta, American Airlines and United Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Overall
Boarding
Comfort
Crew
Entertainment
Food
Reviews
Even if you have delta comfort plus, they will move your overhead bag. One of the perks for upgrading is that you have dedicated space for your carry on with comfort plus with delta. They moved my carry on luggage (3) compartments back and put in bags for other passengers that should have gone under their respective seats. When deboarding the plane, there was no help from anyone to retrieve my luggage back several rows. Delta is turning into pure garbage.
Related info for your journey
Find useful and relevant information for your journey from Chicago to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Key WestSee prices for flight routes from nearby airports that may be better suited for you.
See prices for flight routes from nearby airports that may be better suited for you.
Top 4 airlines flying from Chicago to Key West
Discover the top 4 airlines that operate flights from Chicago to Key West. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,795,183 searches. Data last updated May 4, 2024.
Search flights from Chicago to Key West by cabin class
Find flights from Chicago to Key West, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Hourly flight availability from Chicago to Key West
Find hourly flight availability from Chicago to Key West. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 4, 2024.
| 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
Explore weekly flight availability from Chicago to Key West. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated May 4, 2024.
| Sunday | 2daily flights |
|---|---|
| Monday | 2daily flights |
| Tuesday | 2daily flights |
| Wednesday | 2daily flights |
| Thursday | 2daily flights |
| Friday | 2daily flights |
| Saturday | 2daily flights |
Book a flight to one of these trending destinations
User searches for flights to these destinations increased 20% or more in the past 90 days compared to other destinations
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How does Cheapflights help users find flights from Chicago to Key West?
When you search for this flight from Chicago to Key West, Cheapflights searches on 900+ travel sites to save you time finding great flight deals online. Additionally, we offer filter features so you can choose a preferred cabin class or airline, see different price ranges, and much more so you can book the flight for you.
Why should you use Cheapflights to find cheap flight tickets from Chicago to Key West?
Cheapflights helps you find that perfect flight to Key West from Chicago by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!
Can Cheapflights find flights from Chicago to Key West with no change fees?
Need flexible booking options for your flight to Key West from Chicago? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.
Can Cheapflights notify me if prices for flights from Chicago to Key West become cheaper?
Yes! Start tracking prices for Chicago to Key West flights today and get alerted whenever prices for these flights change. To access this feature, click the bell icon next to the flight deals above, which will prompt you for a valid email address to receive your alerts.