$88 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 5/1. 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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Cheap Flights from Key West to Illinois

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Chicago
Chicagononstop$249
Moline
Moline2 stops$498
St. Louis
St. Louis1 stop$309
Chicago
Chicagononstop$249
Moline
Moline2 stops$498
St. Louis
St. Louis1 stop$309

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 - Mon, Apr 13
American Airlines Logo
6:46 pm - 9:35 pm
EYW
-
ORD
3h 49mnonstop
American Airlines Logo
8:10 am - 12:38 pm
ORD
-
EYW
3h 28mnonstop
$249American Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
11:51 am - 1:00 pm
EYW
-
ORD
26h 09m
2 stops
Multiple Airlines Logo
8:24 pm - 9:09 am
ORD
-
EYW
11h 45m
1 stop
$254Multiple Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
11:51 am - 9:15 am
EYW
-
ORD
22h 24m
1 stop
Multiple Airlines Logo
8:24 pm - 9:09 am
ORD
-
EYW
11h 45m
1 stop
$258Multiple Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
10:44 am - 3:00 pm
ORD
-
EYW
3h 16mnonstop
$259United Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
6:35 pm - 11:43 pm
EYW
-
ORD
6h 08m
1 stop
United Airlines Logo
9:15 am - 5:44 pm
ORD
-
EYW
7h 29m
1 stop
$269United Airlines
Tue, Mar 31 - Mon, Apr 6
Multiple Airlines Logo
12:25 pm - 7:51 pm
EYW
-
ORD
8h 26m
1 stop
Multiple Airlines Logo
7:20 am - 11:30 am
ORD
-
EYW
27h 10m
1 stop
$277Multiple Airlines
Tue, Mar 31 - Mon, Apr 6
American Airlines Logo
6:49 pm - 9:36 pm
EYW
-
ORD
3h 47mnonstop
American Airlines Logo
8:20 am - 12:54 pm
ORD
-
EYW
3h 34mnonstop
$286American Airlines
Tue, Mar 31 - Mon, Apr 6
Spirit Airlines Logo
12:25 pm - 8:01 am
EYW
-
ORD
20h 36m
2 stops
Spirit Airlines Logo
7:31 pm - 11:30 am
ORD
-
EYW
14h 59m
2 stops
$296Spirit Airlines
Sat, Feb 14 - Wed, Feb 18
Delta Logo
5:56 pm - 10:31 pm
EYW
-
MDW
5h 35m
1 stop
Delta Logo
12:45 pm - 7:42 pm
MDW
-
EYW
5h 57m
1 stop
$364Delta
Tue, Feb 24 - Tue, Mar 3
Delta Logo
7:10 am - 11:59 am
EYW
-
MDW
5h 49m
1 stop
Delta Logo
12:45 pm - 7:42 pm
MDW
-
EYW
5h 57m
1 stop
$454Delta
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 $249 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 $249.

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 Sunday being the most expensive.

Good to know

Low seasonApril
Cheapest flight$88
Best time to beat the crowds but there is an average 16% increase 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.

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

    The cheapest time of day to fly to Illinois is generally in the evening, when round-trip flights cost $432 on average. Morning departures are around 10% 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 $476.

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 $304 one-way - $403 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 9222 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

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.

4.0 OkaySean, Jan 2026
BOS - ORD
Read more United Airlines reviews

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.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

Pilot navigated severe weather/snow storm with skill. Described his intentions clearly

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

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

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

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

Information on your arrival and departure airports