$105 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 4/17. 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, 0 bags

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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Flight Deals

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$258
Moline
Moline1 stop$456
Peoria
Peoria1 stop$475
Bloomington
Bloomington2 stops$1,478
St. Louis
St. Louis1 stop$301
Chicago
Chicago1 stop$258
Moline
Moline1 stop$456
Peoria
Peoria1 stop$475
Bloomington
Bloomington2 stops$1,478
St. Louis
St. Louis1 stop$301

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

Thu, Apr 9 - Sun, Apr 12
Spirit Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
Spirit Airlines Logo
5:05 am - 11:30 am
ORD
-
EYW
5h 25m
1 stop
$258Spirit Airlines
Thu, Apr 23 - Mon, Apr 27
Multiple Airlines Logo
4:22 pm - 6:20 pm
EYW
-
ORD
26h 58m
1 stop
Multiple Airlines Logo
8:52 pm - 12:21 pm
ORD
-
EYW
14h 29m
1 stop
$265Multiple Airlines
Wed, Apr 15 - Wed, Apr 22
Multiple Airlines Logo
11:51 am - 10:23 am
EYW
-
ORD
23h 32m
2 stops
Multiple Airlines Logo
8:52 pm - 3:42 pm
ORD
-
EYW
17h 50m
1 stop
$271Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
American Airlines Logo
1:50 pm - 6:16 pm
ORD
-
EYW
3h 26mnonstop
$289American Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
American Airlines Logo
9:45 am - 4:30 pm
ORD
-
EYW
5h 45m
1 stop
$299American Airlines
Thu, Aug 6 - Wed, Aug 12
Delta Logo
6:00 pm - 9:45 pm
EYW
-
MDW
4h 45m
1 stop
Delta Logo
6:00 am - 1:09 pm
MDW
-
EYW
6h 09m
1 stop
$329Delta
Thu, Jul 30 - Mon, Aug 3
Allegiant Air Logo
9:22 pm - 7:00 pm
EYW
-
RFD
22h 38m
1 stop
Allegiant Air Logo
8:39 am - 3:51 pm
RFD
-
EYW
6h 12m
1 stop
$355Allegiant Air
Thu, Jul 30 - Mon, Aug 3
Delta Logo
6:00 pm - 9:45 pm
EYW
-
MDW
4h 45m
1 stop
Delta Logo
1:05 pm - 7:45 pm
MDW
-
EYW
5h 40m
1 stop
$404Delta
Wed, Apr 1 - Sun, Apr 5
United Airlines Logo
3:52 pm - 10:57 pm
EYW
-
PIA
8h 05m
1 stop
United Airlines Logo
8:05 am - 2:51 pm
PIA
-
EYW
5h 46m
1 stop
$475United Airlines
Wed, Apr 1 - Sun, Apr 5
United Airlines Logo
3:52 pm - 10:57 pm
EYW
-
PIA
8h 05m
1 stop
United Airlines Logo
6:30 am - 5:39 pm
PIA
-
EYW
10h 09m
2 stops
$480United Airlines
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Illinois from Key West found in the last 72 hours was to Chicago, at $295 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 $295.

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

The average price for all round-trip flights from Key West to Illinois depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Illinois is generally in the morning, when round-trip flights cost $427 on average. Morning departures are around 2% 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 $434.

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, Wednesday 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 Sunday being the most expensive.

Good to know

Low seasonAugust
Cheapest flight$105
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 39% lower on average.
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.

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 $310 one-way - $349 round-trip

Reviews of the top airlines flying 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.
7.4
United AirlinesOverall score based on 9450 reviews
7.3Comfort
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
Airline reviews

Economy plus was so cramped I could not use my laptop. It was beyond bad.

4.0 OkayBryan, Mar 2026
MCO - ORD
Read more United Airlines reviews

Economy plus was so cramped I could not use my laptop. It was beyond bad.

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

They did the one thing that really matters - got to Chicago early.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

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

Information on your arrival and departure airports