$100+ Cheap flights from Chicago (CHI) to Key West (EYW)
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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Chicago to Key West with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.The best prices from Chicago to Key West are usually found in August or September, booked 82 days in advance, depart on a Tuesday or Wednesday and return on a Thursday
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 noviembre 20, 2024.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Popular in | March |
Cheapest in | August |
Round-trip from | $248 (United Airlines) |
One-way from | $100 (American Airlines) |
Find flight deals from Chicago to Key West
Cheapest flights from Chicago to Key WestExplore the most affordable flight options available from Chicago to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 20, 2024.
Explore the most affordable flight options available from Chicago to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 20, 2024.
This United Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This American Airlines deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Delta deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 11/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
This Mytrip deal was found by Cheapflights users on 11/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
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 2,629,791 searches. Data last updated noviembre 20, 2024.
Fly from
Fly to
Route
Depart
Return
Price
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mar. 12/31
11:02 am-3:13 pm
Nonstop3h 11m
Key West
mar. 1/7
1:50 pm-9:43 pm
1 stop8h 53m
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
dom. 12/15
5:40 am-11:37 am
1 stop4h 57m
Key West
mar. 12/24
1:02 pm-7:14 pm
1 stop7h 12m
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mié. 12/18
6:31 am-1:55 pm
1 stop6h 24m
Key West
mié. 12/25
1:07 pm-3:38 pm
Nonstop3h 31m
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
mié. 12/18
12:44 pm-8:34 pm
1 stop6h 50m
Key West
mié. 12/25
3:50 pm-10:06 pm
1 stop7h 16m
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mié. 12/18
12:09 pm-9:51 am
2 stops20h 42m
Key West
mié. 12/25
5:33 pm-7:47 am
1 stop15h 14m
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mar. 12/10
8:10 am-12:35 pm
Nonstop3h 25m
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mar. 12/17
1:59 pm-8:34 pm
1 stop5h 35m
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
sáb. 2/8
7:20 am-4:22 pm
1 stop8h 02m
ChicagoKey West
MDW - EYW
MDWEYW
Chicago Midway
mar. 11/26
12:43 pm-8:30 pm
1 stop6h 47m
ChicagoKey West
ORD - EYW
ORDEYW
Chicago O'Hare Intl
mar. 12/17
10:55 am-3:01 pm
Nonstop3h 06m
Compare providers for flights from Chicago to Key West
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Chicago to Key West in November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Chicago-Key West flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago-Key West flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago-Key West flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Chicago-Key West flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago-Key West flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Chicago to Key West
Have a flexible travel schedule? Discover the best time to fly to Key West from Chicago with our price prediction graph.
Travel insights for flights from Chicago to Key West
Get recent, data-driven insights about flights from Chicago to Key West including ideal travel times, pricing trends, and more.
How far ahead should I 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 November 15, 2024.
The best time to book flights from Chicago to Key West is 82 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.
What is the cheapest month to book a flight from Chicago to Key West?
Currently, August is the cheapest month in which you can book a flight from Chicago to Key West (average of $328). Flying from Chicago to Key West in March is currently the most expensive (average of $492). 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.
What is the cheapest time of day to fly from CHI to EYW?
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 noviembre 20, 2024.
It’s optimal to fly from Chicago to Key West at noon. By choosing this option you can save up to 40% on the cost of your flight, compared to a flight in the evening.
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 noviembre 20, 2024.
The most flights from CHI to EYW are scheduled on a Monday (3 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (2 on average).
Rainfall in Key West by month
Plan your trip to Key West by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Key West ranges from 1.5 - 6.7 inches per month. September is typically the wettest month, when rainfall can reach 6.7 in. February is typically the driest time to visit Key West when rainfall is around 1.5 in.
Temperature in Key West by month
Plan your trip to Key West by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Key West, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 84.2 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 69.8 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 noviembre 20, 2024.
To help decide which airline to fly from Chicago to Key West, see what other customers have to say about United Airlines, American Airlines and Delta. 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.
Crew
Overall
Food
Entertainment
Comfort
Boarding
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.
Crew
Overall
Food
Entertainment
Comfort
Boarding
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.
Crew
Overall
Food
Entertainment
Comfort
Boarding
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.
Crew
Overall
Food
Entertainment
Comfort
Boarding
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 West
See prices for flight routes from nearby airports that may be better suited for you.
Top 3 airlines flying from Chicago to Key West
Discover the top 3 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 2,629,791 searches. Data last updated noviembre 20, 2024.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$216 | Average$434 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$246 | Average$476 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$263 | Average$481 | FlexibilityNo cancel fee | On-time69% |