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

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How to find the cheapest flight from
Key West (EYW) to Chicago (CHI)

EYW - CHI
Price
$235 - $620
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

March

High demand for flights, 34% potential price rise

Cheapest in

April

Best time to find cheap flights, 42% potential price drop

Average price

$434

Average for round-trip flights in October 2020

Round-trip from

$235

From Key West to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Key West to Chicago?

Saturday flights are generally found to be more expensive for flights from Key West to Chicago. This shouldn’t discourage you from searching, as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Key West to Chicago?

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 20 days in advance, which can save you up to 10% on flights from Key West to Chicago compared to booking the week you need them. Waiting 20 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 $137. For sooner than that we have options available in the next 3 days from $157.

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

April can be a great time to fly to Chicago from Key West with a flight ticket averaging about $135. Cheapflights users have found deals in the month of April for as cheap as $33. The most expensive prices can be found in the month of December.

When is the cheapest time to fly from Key West to Chicago (EYW - CHI)?

When flying from Key West to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 27% versus a flight in the afternoon.

Cheap flights from Key West to Chicago in October, November 2020

The best prices found for EYW to CHI flights for October, November
6 Nov - 8 Nov
$223pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West
6 Nov - 8 Nov
$250pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West
13 Nov - 16 Nov
$256pp
EYW
Key West
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EYW
Key West

Key West to Chicago 2020 flight deals

Cheap flights to Chicago from Key West found for this year
6 Nov - 8 Nov
$223pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West
6 Nov - 8 Nov
$250pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West
13 Nov - 16 Nov
$256pp
EYW
Key West
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
 
1 STOP
EYW
Key West

Non-stop flights to Chicago from Key West

Save time with Key West to Chicago direct flight deals
13 Nov - 16 Nov
$369pp
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
6 Nov - 8 Nov
$492pp
EYW
Key West
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EYW
Key West
7 Dec - 8 Dec
$497pp
EYW
Key West
United Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
Non-Stop
EYW
Key West

Last minute flights from Key West to Chicago

Late deals on round-trip flights to Chicago from Key West, departing today and this week
6 Nov - 8 Nov
$223pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West
6 Nov - 8 Nov
$250pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West
6 Nov - 8 Nov
$318pp
EYW
Key West
United Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
United Airlines
 
1 STOP
EYW
Key West

One-way flights to Chicago from Key West

The cheapest one-way flights from Key West to Chicago
8:55 am - 10:07 am
Multiple Airlines
3 Stops
26h 12m
EYW - ORD
Multiple Airlines
$256
Kiwi.com
7:20 am - 12:16 pm
Delta
1 Stop
5h 56m
EYW - MDW
Delta
$273
Delta
9:45 am - 12:10 pm
United Airlines
Nonstop
3h 25m
EYW - ORD
United Airlines
$296
United

Related info for your journey

Useful info, stats and facts about Key West to Chicago flights.

Flight FAQs

From Key West to Chicago

Are flight prices decreasing from Key West to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Key West and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Key West to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. New policies for travelers booking flights from Key West to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

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 United Airlines for just $223, but on average you can expect to pay $342.

Are there nonstop flights from Key West to Chicago for under $400 on Cheapflights?

Cheapflights has at least 7 direct flights from Key West to Chicago under $400. A good price for a nonstop flight from Key West to Chicago is less than $589.

Are there last-minute flights available from Key West to Chicago for under $300?

There are currently 20+ open flights from Key West to Chicago within the next 7 days for less than $300.

What days are nonstop flights available from Key West to Chicago?

Nonstop flights can be found on the following days: Friday.

How many flights depart from Key West to Chicago on average per day?

1 flight departure from Key West to Chicago per day on average.
Afternoon (Noon - 6pm) - 100% of flight departures

Is Key West weather warmer or cooler than Chicago?

Our data indicates that the weather will be 91 °F on average in the month of August. The temperature in Chicago is typically colder than in Key West. If you're traveling when the temperature is at its warmest, push to plan early, as flight price and availability will have an impact on your travels. For the best results, search for flights well in advance or after peak season.

How long is the flight from Key West to Chicago?

Airlines like United Airlines, American Airlines, and Delta fly from Key West to Chicago in about 3h 25m. The time it takes to get you to your destination can typically vary by up to 1h 23m. There are 1261 mi between Key West and Chicago. This flight may include one or multiple stops.

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

Currently priced at $223, United Airlines will fly you from Key West to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from American Airlines and Delta - these airlines can fly you to your destination from $256 and $378, respectively. United Airlines is currently priced 45% below the average price you’ll pay for this route.

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

For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $118. Users have also found prices from $134 and $253 on United Airlines and American Airlines, respectively.

Alternative routes for Key West to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Key West to Chicago
Flight duration
3h 26m
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing Key West

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Key West to 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
Sunday
1 daily flight
Monday
1 daily flight
Tuesday
1 daily flight
Wednesday
1 daily flight
Thursday
1 daily flight
Friday
1 daily flight
Saturday
1 daily flight
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