Cheap flights from Key West to Chicago (EYW - CHI)

Know your dates, get live prices in seconds:

From
To
Depart
Return
Any month
Compare vs. Cheapflights |
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime
From
To
Depart
Depart
Time
Anytime

We work with more than 300 partners to bring you better travel deals

The best prices from Key West to Chicago are usually found in December or August, booked 27 days in advance, depart on a Friday or Tuesday 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 2022: compare Key West to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
EYW - CHI
Price
$312 - $1,824
CHI
Temperature
23 - 73.4 °F
CHI
Rainfall
1.7 - 4.9 inches

Popular in

April

High demand for flights, 70% potential price rise

Cheapest in

December

Best time to find cheap flights, 44% potential price drop

Round-trip from

$312

From Key West to Chicago (CHI)

One-way from

$228

One-way flight from Key West to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
How far in advance should I book a flight from Key West to Chicago?

Travelers have found it’s best to book a flight 27 days in advance to save up to 64% 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 27 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 $438, or $649 for flights within the next 24 hours.

What is the cheapest month to fly from Key West to Chicago?

December can be a great time to fly to Chicago from Key West with a flight ticket averaging about $552. Cheapflights users have found deals in the month of December for as cheap as $228. The most expensive prices can be found in the month of April.

What is the cheapest day to fly round-trip from Key West to Chicago?

Thursday is generally a great day to depart. Flying on this day could help you save up to 164%.

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 30% on your trip compared to booking a flight in the evening.

Cheap flights from Key West to Chicago in August, September 2022

The best prices found for EYW to CHI flights for August, September
9 Sep - 13 Sep
$266pp
EYW
Key West
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
EYW
Key West
9 Sep - 13 Sep
$302pp
EYW
Key West
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
EYW
Key West
18 Aug - 22 Aug
$311pp
EYW
Key West
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
EYW
Key West

Key West to Chicago 2022 flight deals

Cheap flights to Chicago from Key West found for this year
9 Sep - 13 Sep
$266pp
EYW
Key West
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
EYW
Key West
5 Oct - 11 Oct
$299pp
EYW
Key West
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
EYW
Key West
9 Sep - 13 Sep
$302pp
EYW
Key West
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
EYW
Key West

Cheap Delta flights from Key West to Chicago

9 Sep - 13 Sep
$266pp
EYW
Key West
Delta
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Delta
 
1 STOP
EYW
Key West
5 Oct - 11 Oct
$299pp
EYW
Key West
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
EYW
Key West
9 Sep - 13 Sep
$302pp
EYW
Key West
Delta
 
1 STOP
MDW
Chicago Midway
MDW
Chicago Midway
Delta
 
1 STOP
EYW
Key West

Cheap United Airlines flights from Key West to Chicago

5 Jan - 11 Jan
$347pp
EYW
Key West
United Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EYW
Key West
9 Sep - 13 Sep
$351pp
EYW
Key West
United Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West
5 Jan - 11 Jan
$362pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EYW
Key West

Non-stop flights to Chicago from Key West

Save time with Key West to Chicago direct flight deals
5 Jan - 11 Jan
$419pp
EYW
Key West
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EYW
Key West
23 Nov - 29 Nov
$630pp
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West

One-way flights to Chicago from Key West

The cheapest one-way flights from Key West to Chicago
5:30 am - 9:11 am
Allegiant Air
3 Stops
28h 41m
EYW - MDW
Allegiant Air
$228
Kiwi.com
1:00 pm - 3:27 am
American Airlines
2 Stops
15h 27m
EYW - ORD
American Airlines
7:45 am - 10:55 am
United Airlines
1 Stop
28h 10m
EYW - ORD
United Airlines
$249
United

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Key West</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Key West to Chicago

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 0 outbound flights to Chicago per day from 3 airlines. Key West is conveniently located just 2.6 mi from Key West’s city center.

Which airlines flying from Key West to Chicago have flexible cancellations due to COVID-19?

Due to the rapidly changing circumstances due to COVID-19, airlines like American Airlines, United Airlines, and Delta flying from Key West to Chicago have implemented new flexible cancellation policies.

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 Delta for just $266, but on average you can expect to pay $363.

Are there nonstop flights from Key West to Chicago for under $500 on Cheapflights?

Cheapflights has at least 2 direct flights from Key West to Chicago under $500. A good price for a nonstop flight from Key West to Chicago is less than $524.

What are the cheapest airlines flying from Key West to Chicago round-trip?

Flying on Delta is currently your cheapest option to Chicago, with prices starting at $266. Additional round-trip tickets that might be worth considering are offered by United Airlines and American Airlines, with the lowest prices starting at $347 and $434, respectively. Delta is priced at 51% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Key West to Chicago one-way?

The cheapest airline one-way is Allegiant Air, with whom users have recently found tickets for as low as $187. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Key West to Chicago for a low price.

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 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 cheapest flights from Key West to Chicago?

Looking for the cheapest flight from Key West to Chicago? While on average our users pay $510, our data indicates the cheapest price to be $218. The most popular route (Key West - Chicago O'Hare Intl), is priced around $324.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Key West?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Key West need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Key West are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Key West are not required to quarantine after entering Chicago.

Do I need a test to fly back to Key West from Chicago?

Returning to Key West from Chicago

COVID-19 testing requirements
Visitors from Chicago are not required to present a negative COVID-19 PCR test or antigen result upon entering Key West.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Key West.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Key West to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

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.
Airline Cheapest Average Flexibility On-time COVID-19 safety
American Airlines
$188 $479 No cancel fee 71%
United Airlines
$188 $433 No cancel fee 69%
Delta
$316 $474 No cancel fee N/A

Hourly flight availability from Key West to Chicago

See what time of day planes typically take off from Key West towards Chicago.
Afternoon Noon to 6 PM 100% of EYW to CHI departures
Early morning Midnight to 6 AM 0% of EYW to CHI departures
Morning 6 AM to noon 0% of EYW to CHI departures
Evening 6 PM to midnight 0% of EYW to CHI departures
Midnight
6 AM
Noon
6 PM
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
0 flights
Monday
0 flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
0 flights
Friday
0 flights
Saturday
3 daily flights