Question 1

How long does a flight from Key West to Chicago take?

Accepted Answer

The duration of a nonstop flight to Chicago from Key West is typically 3h 33m. The journey crosses a distance of 1,242 miles.

Question 2

How many flights are there between Key West and Chicago per day?

Accepted Answer

Each day, there are 2 nonstop flights that take off from Key West and land in Chicago, with an average flight time of 3h 51m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 14 flights and there are the same amount of flights each day (2).

Question 3

How many flights are there between Key West and Chicago per day?

Accepted Answer

Each day, there are 2 nonstop flights that take off from Key West and land in Chicago, with an average flight time of 3h 51m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 14 flights and there are the same amount of flights each day (2).

Question 4

What is the cheapest flight from Key West to Chicago?

Accepted Answer

In the last 5 days, the lowest price for a flight from Key West to Chicago was $109 for a one-way ticket and $276 for a round-trip.

Question 5

Do I need a passport to fly between Key West and Chicago?

Accepted Answer

A passport is not required to fly from Key West to Chicago.

Question 6

What’s the cheapest day of the week to fly from Key West to Chicago?

Accepted Answer

When flying from Key West to Chicago, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Key West, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

Question 7

What’s the cheapest day of the week to fly from Key West to Chicago?

Accepted Answer

When flying from Key West to Chicago, you should consider leaving on a Wednesday and avoid Mondays if you are looking for the best rates. For your return to Key West, you’ll find the best rates on Tuesdays and the most expensive ones on Sundays.

Question 8

Which airports will I be using when flying from Key West to Chicago?

Accepted Answer

When flying out of Key West you will be using Key West. You will be landing at one of these airports: Chicago Midway or Chicago O'Hare Intl.

Question 9

What’s the earliest departure time from Key West to Chicago?

Accepted Answer

Early birds can take the earliest flight from Key West at 4:00 pm and will be landing in Chicago at 6:55 pm.

Question 10

What’s the latest departure time from Key West to Chicago?

Accepted Answer

If you prefer to fly at night, the latest flight from Key West to Chicago jets off at 4:58 pm and lands at 7:50 pm.

Question 11

Which airlines fly non-stop between Key West and Chicago?

Accepted Answer

There is just one airline that flies from Key West to Chicago direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is $329.

Question 12

Which airlines fly non-stop between Key West and Chicago?

Accepted Answer

There is just one airline that flies from Key West to Chicago direct and that is American Airlines. The best round-trip deal found from American Airlines for the route is $329.

Question 13

Which airlines offer Wi-Fi service onboard planes from Key West to Chicago?

Accepted Answer

Only American Airlines offers inflight Wi-Fi service on the Key West to Chicago flight route.

Question 14

Which aircraft models fly most regularly from Key West to Chicago?

Accepted Answer

The Embraer 170 is the aircraft model that flies most regularly on the Key West to Chicago flight route.

Question 15

Which airline alliances offer flights from Key West to Chicago?

Accepted Answer

oneworld is the only airline alliance operating flights between Key West and Chicago.

Question 16

On which days can I fly direct from Key West to Chicago?

Accepted Answer

There are nonstop flights from Key West to Chicago on a daily basis.

Question 17

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

Accepted Answer

The cheapest month for flights from Key West to Chicago is March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are January and April, where the average cost of round-trip tickets is $884 and $574 respectively.

Question 18

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

Accepted Answer

The cheapest month for flights from Key West to Chicago is March, where tickets cost $0 (return) on average. On the other hand, the most expensive months are January and April, where the average cost of round-trip tickets is $884 and $574 respectively.

Question 19

How does KAYAK find such low prices on flights from Key West to Chicago?

Accepted Answer

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Chicago.

Question 20

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Chicago?

Accepted Answer

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Key West is likely to change within 7 days, so travelers know whether to wait or book now.

Question 21

What is the Hacker Fare option on flights from Key West to Chicago?

Accepted Answer

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Key West with another airline.

Question 22

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Chicago?

Accepted Answer

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Key West up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Question 23

What is the cheapest layover airport when flying from Key West to Chicago?

Accepted Answer

Flights via Miami (MIA) offer the most affordable fares, with an average round-trip price of $370.

Question 24

What is the most popular layover airport when flying from Key West to Chicago?

Accepted Answer

Atlanta (ATL) is the top choice – 71% of KAYAK users who clicked on 1-stop flights from Key West to Chicago picked an itinerary connecting there.

Question 25

Which layover airport has the quickest connection when flying from Key West to Chicago?

Accepted Answer

If you prefer a quick connection, Atlanta (ATL) often has the shortest layovers from Key West to Chicago, with an average of 1h 19m.

Question 26

Which layover airport offers the shortest total travel time from Key West to Chicago?

Accepted Answer

Consider flying via Atlanta (ATL) for the shortest journey. The average one-way travel time for flights connecting there is 5h 41m.

Question 27

Which cabin class options are there for flights between Key West and Chicago?

Accepted Answer

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 28

Which cabin class options are there for flights between Key West and Chicago?

Accepted Answer

There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

Question 29

Which airlines provide the cheapest flights from Key West to Chicago?

Accepted Answer

In the past 5 days, the cheapest round-trip tickets from Key West to Chicago were found on American Airlines ($309) and Delta ($316).

Question 30

Which airlines provide the cheapest flights from Key West to Chicago?

Accepted Answer

In the past 5 days, the cheapest round-trip tickets from Key West to Chicago were found on American Airlines ($309) and Delta ($316).

Question 31

What is the cheapest Key West to Chicago flight route?

Accepted Answer

The cheapest return flight from Key West to Chicago costs $309 on the route between Key West (EYW) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

Question 32

What is the cheapest Key West to Chicago flight route?

Accepted Answer

The cheapest return flight from Key West to Chicago costs $309 on the route between Key West (EYW) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

Question 33

Can I save money by flying with a layover from Key West to Chicago?

Accepted Answer

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $332 on average.

Question 34

Can I save money by flying with a layover from Key West to Chicago?

Accepted Answer

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $332 on average.

EYW - CHI

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Everything you should know

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

Recent round-trip flight deals from Key West to Chicago

Recent one-way flight deals from Key West to Chicago

Recent last minute flight deals from Key West to Chicago

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KAYAK's insights & trends for Key West to Chicago flights

What is the cheapest Key West to Chicago flight route?

What’s the cheapest day of the week to fly from Key West to Chicago?

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

Can I save money by flying with a layover from Key West to Chicago?

Which airlines provide the cheapest flights from Key West to Chicago?

Which airlines fly non-stop between Key West and Chicago?

What is the most popular layover airport when flying from Key West to Chicago?

What is the cheapest layover airport when flying from Key West to Chicago?

Which layover airport offers the shortest total travel time from Key West to Chicago?

Which layover airport has the quickest connection when flying from Key West to Chicago?

Which cabin class options are there for flights between Key West and Chicago?

How many flights are there between Key West and Chicago per day?

How long does a flight from Key West to Chicago take?

What’s the earliest departure time from Key West to Chicago?

What’s the latest departure time from Key West to Chicago?

Expert advice for your flight from Key West to Chicago

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Everything you need to know for your flight from Key West to Chicago

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