$173 Find Cheap Flights from Key West to Illinois

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Illinois departing on 8/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Illinois

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Illinois, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Illinois, as well as popular online travel agencies
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Cheap Flights from Key West to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicago1 stop$269
Moline
Moline1 stop$906
Peoria
Peoria1 stop$374
Bloomington
Bloomington1 stop$348
St. Louis
St. Louis1 stop$223
Chicago
Chicago1 stop$269
Moline
Moline1 stop$906
Peoria
Peoria1 stop$374
Bloomington
Bloomington1 stop$348
St. Louis
St. Louis1 stop$223

Book Cheap Key West to Illinois Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Illinois that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Illinois

Wed, Sep 3 - Mon, Sep 8
Delta Logo
6:20 pm - 10:37 pmEYW-ORD
5h 17m1 stop
Delta Logo
5:45 am - 1:05 pmORD-EYW
6h 20m1 stop
$269Delta
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Wed, Sep 3 - Tue, Sep 9
Delta Logo
7:00 am - 1:36 pmEYW-MDW
7h 36m1 stop
Delta Logo
6:00 am - 1:05 pmMDW-EYW
6h 05m1 stop
$269Delta
Find Deal
Fri, Sep 12 - Wed, Sep 17
Delta Logo
6:10 pm - 11:54 pmEYW-ORD
6h 44m1 stop
Delta Logo
5:30 am - 10:55 amORD-EYW
4h 25m1 stop
$289Delta
Find Deal
Wed, Aug 13 - Tue, Aug 19
Delta Logo
7:00 am - 11:48 amEYW-MDW
5h 48m1 stop
Delta Logo
12:43 pm - 8:12 pmMDW-EYW
6h 29m1 stop
$289Delta
Find Deal
Fri, Sep 5 - Sun, Sep 7
United Airlines Logo
3:50 pm - 11:25 pmEYW-ORD
8h 35m1 stop
United Airlines Logo
6:00 am - 2:01 pmORD-EYW
7h 01m1 stop
$299United Airlines
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Thu, Aug 14 - Tue, Aug 19
 Logo
10:02 am - 10:22 pmEYW-ORD
13h 20m1 stop
 Logo
8:12 pm - 1:23 pmORD-EYW
16h 11m2 stops
Fri, Sep 5 - Sun, Sep 7
 Logo
8:47 am - 9:58 pmEYW-ORD
14h 11m1 stop
 Logo
6:44 pm - 2:54 pmORD-EYW
19h 10m2 stops
Wed, Aug 27 - Wed, Sep 3
American Airlines Logo
12:10 pm - 7:26 pmEYW-ORD
8h 16m1 stop
American Airlines Logo
8:20 am - 5:46 pmORD-EYW
8h 26m2 stops
$352American Airlines
Find Deal
Wed, Aug 27 - Wed, Sep 3
American Airlines Logo
1:13 pm - 9:11 pmEYW-ORD
8h 58m2 stops
American Airlines Logo
9:51 am - 6:59 pmORD-EYW
8h 08m2 stops
$357American Airlines
Find Deal
Wed, Aug 13 - Tue, Aug 19
United Airlines Logo
2:12 pm - 9:28 pmEYW-ORD
8h 16m1 stop
United Airlines Logo
6:00 am - 2:25 pmORD-EYW
7h 25m1 stop
$369United Airlines
Find Deal
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 price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Key West to Illinois.

The cheapest ticket to Illinois from Key West found in the last 72 hours was to Chicago, at $344 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 72 hours was $344.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $295 on average.

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

The average price of all round-trip flights from Key West to Illinois clicked on KAYAK for each day over the last 12 months.

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


Good to know

Low seasonFebruary
Cheapest flight$173
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Key West to Bloomington

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.

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

    The cheapest time of day to fly to Illinois is generally in the afternoon, when round-trip flights cost $359 on average. Morning departures are around 14% more expensive than evening flights, on average. The most expensive time of day to fly to Illinois is generally in the morning, which is peak travel time and where the average cost of a ticket is $507.

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 $305 one-way - $415 round-trip

Reviews of the top 3 airlines serving from Key West to Illinois

 
See real verified KAYAK customer reviews for airlines flying from Key West to Illinois. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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.
8.0
DeltaOverall score based on 7980 reviews
7.9Comfort
8.5Crew
7.3Food
8.2Boarding
7.9Entertainment
Airline reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

2.0 MediocreRosa, Jul 2025TPA - JFK
Read more Delta reviews

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

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

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