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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)

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 37 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 37 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 $177. For sooner than that we have options available in the next 3 days from $177.

Cheap flights from Key West to Chicago in July, August 2020

The best prices found for EYW to CHI flights for July, August
1 Jul - 14 Jul
$241pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
1 Jul - 8 Jul
$244pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
2 Jul - 5 Jul
$262pp
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West

Key West to Chicago 2020 flight deals

Cheap flights to Chicago from Key West found for this year
1 Jul - 14 Jul
$241pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
1 Jul - 8 Jul
$244pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
2 Jul - 5 Jul
$262pp
EYW
Key West
Multiple Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 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
25 Jun - 29 Jun
$288pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
25 Jun - 3 Jul
$330pp
EYW
Key West
Multiple Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Multiple Airlines
 
1 STOP
EYW
Key West
26 Jun - 3 Jul
$338pp
EYW
Key West
Multiple Airlines
 
1 STOP
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

The cheapest one-way flights from Key West to Chicago
10:39 am - 3:11 pm
Spirit Airlines
1 Stop
5h 32m
EYW - ORD
Spirit Airlines
$215
Ovago
12:55 pm - 8:46 pm
JetBlue
1 Stop
8h 51m
EYW - ORD
JetBlue
11:59 am - 5:06 pm
Allegiant Air
1 Stop
6h 07m
EYW - ORD
Allegiant Air
$290
Ovago

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.

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 Multiple Airlines for just $241, but on average you can expect to pay $435.

Are there nonstop flights from Key West to Chicago for under $200 on Cheapflights?

There are no nonstop flights from Key West to Chicago, but Cheapflights can provide you with all the information you need to find the fastest route with the fewest stops.

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 is the cheapest airline for this route?

While looking for the best option consider American Eagle, Inc., our data currently shows that they have the cheapest flight available for the flight path. When traveling from Key West to Chicago, generally 169 flights depart for this route daily.

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.

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
Average temperature for July in Chicago
84.2 °F
Avg rainfall for July in Chicago
3.7 ″

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
0 flights
Monday
0 flights
Tuesday
0 flights
Wednesday
0 flights
Thursday
0 flights
Friday
0 flights
Saturday
3 daily flights