Cheap flights from Key West (EYW) to Chicago (CHI) from $150
This is the cheapest one-way flight price, found on 9/20. Prices may vary by date and flight preferences.
The best prices from Key West to Chicago are usually found in January or October, booked 38 days in advance, depart on a Tuesday or Monday and return on a Tuesday
How to find the cheapest flight from Key West (EYW) to Chicago (CHI)
All the information you need to plan the best EYW to CHI flight in 2023: compare Key West to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
Popular in | April |
|---|---|
Cheapest in | January |
Round-trip from | $207 |
One-way from | $150 |
EYW - CHI Price | $207 - $364 |
|---|---|
CHI Temperature | 23 - 73.4 °F |
CHI Rainfall | 1.7 - 4.9 inches |
What is the cheapest day to fly round-trip from Key West to Chicago?
Wednesday is generally a great day to depart. Flying on this day could help you save up to 37%.
How far in advance should I book a flight from Key West to Chicago?
Travelers have found it’s best to book a flight 38 days in advance to save up to 76% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 38 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Key West to Chicago 1-2 weeks in advance for as low as $544, or $820 for flights within the next 24 hours.
What is the cheapest month to fly from Key West to Chicago?
January can be a great time to fly to Chicago from Key West with a flight ticket averaging about $597. Cheapflights users have found deals in the month of January for as cheap as $241. The most expensive prices can be found in the month of April.
When is the cheapest time to fly from Key West to Chicago (EYW - CHI)?
A simple way to save on the total cost of your ticket is to fly from Key West to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 27% on your trip compared to booking a flight in the morning.
Cheap American Airlines flights from Key West to Chicago
Find some of the cheapest American Airlines flights traveling from Key West to Chicago. Make sure to double check the flight details before booking.
Cheap United Airlines flights from Key West to Chicago
Browse through some of the cheapest United Airlines flights traveling from Key West to Chicago. Check back soon if you're not seeing flights that suit your needs.
Cheap Key West to Chicago flights in September & October 2023
The best prices found for EYW to CHI flights for September, October
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.
Key West to Chicago 2023 flight deals
Cheap flights to Chicago from Key West found for this year
These are some of the best deals we've found on flights to Chicago in 2023 at this time. Check back soon for alternative fares.
Non-stop flights to Chicago from Key West
Save time with Key West to Chicago direct flight deals
For a quicker trip, book one of these direct flights from Key West to Chicago. Users seeking other options on flights from Key West to Chicago should update the search form at the top of the page.
One-way flights to Chicago from Key West
The cheapest one-way flights from Key West to Chicago
Take a look at some of the best available options we've come across on one-way flights from Key West to Chicago. For those needing a return trip from Key West, there is a search form available above.
Find flights from Key West to Chicago within your budget
Use the slider to find flights from Key West to Chicago that fit your budget.
Fly from
Fly to
Budget
$208 - $418
Route
Depart
Return
Price
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 1/11
Nonstop3h 27m
Chicago O'Hare Intl
Mon 1/15
Nonstop3h 13m
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 1/11
1 stop5h 15m
Chicago O'Hare Intl
Mon 1/15
Nonstop3h 13m
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 1/11
1 stop5h 07m
Chicago O'Hare Intl
Mon 1/15
1 stop7h 06m
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Thu 1/11
1 stop4h 47m
Chicago Midway
Mon 1/15
1 stop5h 51m
Key WestChicago Midway
EYW - MDW
EYWMDW
Key West
Fri 1/12
1 stop18h 01m
Chicago Midway
Mon 1/15
1 stop17h 10m
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Tue 10/31
1 stop8h 25m
Chicago O'Hare Intl
Thu 11/2
1 stop6h 51m
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Tue 10/31
1 stop8h 25m
Chicago O'Hare Intl
Thu 11/2
2 stops13h 45m
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Fri 1/12
2 stops19h 53m
Chicago O'Hare Intl
Mon 1/15
1 stop8h 15m
Key WestChicago O'Hare Intl
EYW - ORD
EYWORD
Key West
Thu 1/11
2 stops9h 59m
Chicago O'Hare Intl
Mon 1/15
1 stop8h 15m
Reviews of airlines servicing Chicago
Read reviews from past customers who have flown American Airlines, United Airlines and Delta from Key West to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
Food
Crew
Entertainment
Boarding
Overall
Reviews
The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up
Comfort
Food
Crew
Entertainment
Boarding
Overall
Reviews
The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up
Comfort
Food
Crew
Entertainment
Boarding
Overall
Reviews
The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up
Comfort
Food
Crew
Entertainment
Boarding
Overall
Reviews
The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up
Comfort
Food
Crew
Entertainment
Boarding
Overall
Reviews
The seats were wayyyy too small! If you are a larger person buying 2 seats would not work as arm rests do not go up
Related info for your journey
Useful info, stats and facts about Key West to Chicago flights.
What airport do you fly from for flights from Key West to Chicago?
Most people fly from Key West (EYW) if they book a flight from Key West to Chicago. On average, Key West has 3 outbound flights to Chicago per day from 3 airlines. Key West is conveniently located just 2.6 mi from Key West’s city center.
Can I find flights from Key West to Chicago for under $300 on Cheapflights?
Yes, there are multiple flights from Key West to Chicago for under $300. The cheapest flight booked recently is on American Airlines for just $208, but on average you can expect to pay $410.
Are there nonstop flights from Key West to Chicago for under $300 on Cheapflights?
Cheapflights has at least 1 direct flight from Key West to Chicago under $300. A good price for a nonstop flight from Key West to Chicago is less than $208.
What are the cheapest airlines flying from Key West to Chicago round-trip?
Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $208. Additional round-trip tickets that might be worth considering are offered by Delta and United Airlines, with the lowest prices starting at $227 and $364, respectively. American Airlines is priced at 65% lower than the current average price of a flight leaving 3 months from now.
What are the most popular routes from Key West to Chicago?
The most popular flight routes from Key West to Chicago are Key West - Chicago O'Hare Intl, Key West - Chicago Midway and Key West - Chicago Greater Rockford.
What are the most popular airlines that fly from Key West to Chicago?
Before booking your flight from Key West to Chicago check out the most popular airlines for this route: American Airlines, Delta or United Airlines.
What are the cheapest flights from Key West to Chicago?
Looking for the cheapest flight from Key West to Chicago? While on average our users pay $313, our data indicates the cheapest price to be $252. The most popular route (Key West - Chicago O'Hare Intl), is priced around $227.
What does EYW to ORD mean?
EYW and ORD are unique codes to identify airports used in the aviation industry. They are defined by IATA (International Air Transport Association) and are commonly called IATA codes. EYW to ORD refers to a flight route from Key West Airport to Chicago O'Hare Intl Airport. This flight route has multiple associated airports, so we think it might be helpful to learn the name and codes of them as well. They are Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).
Other flights from Key West
Top 3 airlines flying from Key West to Chicago
The chart below displays the airlines Cheapflights users traveling from Key West to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Weekly flight availability from Key West to Chicago
See how many times per day planes take to the skies headed from Key West to Chicago
| Sunday | 3daily flights |
|---|---|
| Monday | 3daily flights |
| Tuesday | 3daily flights |
| Wednesday | 3daily flights |
| Thursday | 3daily flights |
| Friday | 3daily flights |
| Saturday | 3daily flights |