$109+ Cheap flights from Key West (EYW) to Chicago (CHI)
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 2/5. Fares are subject to change and may not be available on all flights or dates of travel.
Find cheap flights from Key West to Chicago 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.Cheap flight deals from Key West to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Key West (EYW) to Chicago (CHI). 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 January 20, 2025.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $217 (Delta) |
One-way from | $109 (Delta) |
Popular in | September |
Cheapest in | August |
Average price | $359 |
Find flight deals from Key West to Chicago
Cheapest flights from Key West to ChicagoExplore the most affordable flight options available from Key West to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2025.
Explore the most affordable flight options available from Key West to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 20, 2025.
This United Airlines deal was found by Cheapflights users on 1/20. 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 1/20. 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 Delta deal was found by Cheapflights users on 1/20. 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 1/20. 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 Mytrip deal was found by Cheapflights users on 1/19. 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 Key West to Chicago within your budget
Customize your flight search to find flights from Key West to Chicago 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 2,558,603 searches. Data last updated January 20, 2025.
Fly from
Fly to
Route
Depart
Return
Price
Key WestChicago
EYW - MDW
EYWMDW
Key West
Wed 3/5
6:14 pm-10:20 pm
1 stop5h 06m
Chicago Midway
Wed 3/12
12:51 pm-8:30 pm
1 stop6h 39m
Key WestChicago
EYW - ORD
EYWORD
Key West
Tue 3/4
4:07 pm-6:49 pm
Nonstop3h 42m
Chicago O'Hare Intl
Mon 3/10
4:42 pm-9:03 pm
Nonstop3h 21m
Key WestChicago
EYW - ORD
EYWORD
Key West
Tue 3/4
6:14 pm-11:49 pm
1 stop6h 35m
Chicago O'Hare Intl
Mon 3/10
2:30 pm-8:30 pm
1 stop5h 00m
Key WestChicago
EYW - ORD
EYWORD
Key West
Thu 3/6
8:53 am-7:44 am
3 stops23h 51m
Chicago O'Hare Intl
Wed 3/12
7:21 pm-8:03 am
1 stop11h 42m
Key WestChicago
EYW - ORD
EYWORD
Key West
Sun 2/16
2:08 pm-8:10 pm
1 stop7h 02m
Chicago O'Hare Intl
Sun 2/23
8:12 am-3:23 pm
1 stop6h 11m
Key WestChicago
EYW - ORD
EYWORD
Key West
Wed 2/5
3:03 pm-8:46 pm
1 stop6h 43m
Key WestChicago
EYW - ORD
EYWORD
Key West
Tue 3/18
10:19 am-1:09 pm
Nonstop3h 50m
Key WestChicago
EYW - MDW
EYWMDW
Key West
Fri 2/28
2:00 pm-9:25 pm
1 stop8h 25m
Key WestChicago
EYW - ORD
EYWORD
Key West
Sun 2/9
5:52 pm-12:39 pm
2 stops19h 47m
Key WestChicago
EYW - ORD
EYWORD
Key West
Tue 5/6
1:50 pm-4:15 pm
Nonstop3h 25m
Compare providers for flights from Key West to Chicago
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 Key West to Chicago in January.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Key West-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Key West-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Key West-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Key West-Chicago 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 Key West-Chicago 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 Key West to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Key West with our price prediction graph.
Travel insights for flights from Key West to Chicago
Get recent, data-driven insights about flights from Key West to Chicago including ideal travel times, pricing trends, and more.
What is the cheapest month to book a flight from Key West to Chicago?
Currently, August is the cheapest month in which you can book a flight from Key West to Chicago (average of $245). Flying from Key West to Chicago in March is currently the most expensive (average of $320). 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 EYW to CHI?
Find hourly flight availability from Key West to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 20, 2025.
A simple way to save on the total cost of your ticket is to fly from Key West to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 6% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Key West to Chicago
Explore weekly flight availability from Key West to Chicago. 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 January 20, 2025.
The most flights from EYW to CHI are scheduled on a Monday (4 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).
Rainfall in Chicago by month
Plan your trip to Chicago by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.
Temperature in Chicago by month
Plan your trip to Chicago by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated January 20, 2025.
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Boarding
Overall
Crew
Comfort
Entertainment
Food
Reviews
Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
Related info for your journey
Find useful and relevant information for your journey from Key West to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Key West?
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Alternative routes for Key West to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 2 airlines flying from Key West to Chicago
Discover the top 2 airlines that operate flights from Key West to Chicago. 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 2,558,603 searches. Data last updated January 20, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$211 | Average$392 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$224 | Average$394 | FlexibilityNo cancel fee | On-time69% |