$118 Find Cheap Flights from Key West to Illinois - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Key West to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Chicago
3h 39mNonstop
from $303per person
Moline
5h 11m2 stops
from $545per person
Peoria
8h 03m4 stops
from $708per person
Booking Insights

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

Get data-powered insights and trends into flights from Key West to Illinois to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Key West to Illinois flight route?

The cheapest ticket to Illinois from Key West found in the last 5 days was to Chicago, at $495 round-trip. The most popular route is from Key West (EYW) to Chicago O'Hare Intl Airport (ORD), and the cheapest round-trip airline ticket found on this route in the last 5 days was $495.

What is the cheapest time of day to fly to Illinois?

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $366 on average. Morning departures are around 18% cheaper than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the evening, which is peak travel time and where the average cost of a ticket is $443.

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

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 $339 on average.

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

The cheapest month for flights from Key West to Illinois is March, when tickets cost $0 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $605 and $574 respectively.

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

For Key West to Illinois, Wednesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Illinois back to Key West, the best deals are generally found on Tuesday, with Sunday being the most expensive.

Good to know

Cheapest flight

$118
Flight from Key West to Chicago O'Hare Airport

FAQs - booking Illinois flights

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

    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 Illinois.

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

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

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

    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 from Key West to Illinois with an airline and back with another airline.

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

    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 from Key West to Illinois up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

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

    There is a maximum of 1 nonstop flight a day that takes off from Key West and lands in Illinois, with an average flight time of 3h 39m. The most common departure time is 4:00 pm and most flights take off in the afternoon. Each week, there are 1 flights.

Top tips for finding cheap flights to Illinois

  • Looking for a cheap flight? 25% of our users found tickets from Key West to the following destinations at these prices or less: Chicago $318 one-way - $577 round-trip

Reviews of the top airline flying from Key West to Illinois

 
Need help choosing which airline to fly with from Key West to Illinois? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.1
American AirlinesOverall score based on 12075 reviews
7.2Comfort
6.8Entertainment
7.9Crew
6.4Food
7.4Boarding
Airline reviews

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

2.0 MediocreMargarita, Sep 2026
Read more American Airlines reviews

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

I have never been assaulted they way I was today in Charlotte - shame on American

The staff are very, very professional. It's what flying should feel like.

Waited for oxygen tanks for 30 minutes after boarding was complete.

Little warm on the plane and delayed for an hour

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

More options for your flight from Key West to Illinois

Complete your trip to Illinois with a hotel stay or car rental