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

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How to find the cheapest flight from
Key West International (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

Round-trip from

$235

From Key West International to Chicago

One-way from

$118

One-way flight from Key West International 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 International to Chicago?

Users have found that leaving on a Tuesday can be a cost-effective option. It’s possible to save up to 51% on your flight compared to booking on days when demand is much higher.

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

Find a great deal and save up to 10% by booking at least 20 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Key West International to Chicago within the next two weeks, with the cheapest ticket starting at $137.

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

Our data shows that April tends to be the cheapest month to fly to Chicago from Key West International. Users have commonly found prices around $135 for the month, but tickets can be as low as $33. Due to multiple factors, prepare for potentially higher prices in December.

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

One of the essential ways to save on airfare from Key West International to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 27% on airfare.

Cheap flights from Key West International to Chicago in January, February 2021

5 Feb - 7 Feb
$209pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
5 Feb - 7 Feb
$220pp
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
27 Jan - 31 Jan
$239pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West

Key West International to Chicago 2021 flight deals

5 Feb - 7 Feb
$209pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
5 Feb - 7 Feb
$220pp
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
27 Jan - 31 Jan
$239pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West

Non-stop flights to Chicago from Key West International

27 Feb - 2 Mar
$523pp
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
12 Feb - 15 Feb
$527pp
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West
5 Feb - 7 Feb
$669pp
EYW
Key West
American Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Non-Stop
EYW
Key West

Last minute flights from Key West International to Chicago

5 Feb - 7 Feb
$209pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
5 Feb - 7 Feb
$220pp
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
5 Feb - 7 Feb
$240pp
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
   
2 STOPS
EYW
Key West

One-way flights to Chicago from Key West International

6:00 am - 2:06 pm
United Airlines
1 Stop
9h 06m
EYW - ORD
United Airlines
$118
United
7:00 am - 7:20 pm
Multiple Airlines
3 Stops
37h 20m
EYW - ORD
Multiple Airlines
$156
Gotogate
10:25 am - 5:43 pm
JetBlue
1 Stop
8h 18m
EYW - ORD
JetBlue

Related info for your journey

Flight FAQs

From Key West International 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 International to Chicago for under $300 on Cheapflights?

Yes, there are multiple flights from Key West International to Chicago for under $300. The cheapest flight booked recently is on United Airlines for just $287, but on average you can expect to pay $3,836.

Are there nonstop flights from Key West International to Chicago for under $600 on Cheapflights?

Cheapflights has at least 3 direct flights from Key West International to Chicago under $600. A good price for a nonstop flight from Key West International to Chicago is less than $573.

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

There are currently 8+ open flights from Key West International 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: Thursday, Saturday.

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

2 flight departures from Key West to Chicago per day on average.
Morning (6am - Noon) - 50% of flight departures
Afternoon (Noon - 6pm) - 50% 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 International to Chicago?

For as low as $523, American Airlines can have you in Chicago from Key West International in 3h 35m. The distance between Key West International and Chicago is about 1261 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

According to our current data, United Airlines ($287), American Airlines ($304), and Delta ($437) offers the cheapest pricing from Key West International to Chicago. United Airlines is priced at 29% lower than the current average price of a flight leaving 3 months from now.

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

One-way options have recently been found by users for as low as $109 on United Airlines. Another option is JetBlue, who have fights from $127.

Alternative routes for Key West International to Chicago

Destination information for Chicago

Flight duration
3h 27m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Key West

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Hourly flight availability from Key West International to Chicago

Afternoon Noon to 6 PM 93% of EYW to CHI departures
Morning 6 AM to noon 6% of EYW to CHI departures
Early morning Midnight to 6 AM 1% 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 International to Chicago
Sunday
1 daily flight
Monday
2 daily flights
Tuesday
2 daily flights
Wednesday
2 daily flights
Thursday
2 daily flights
Friday
1 daily flight
Saturday
1 daily flight
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