$87 Find Cheap Flights from Key West to Wisconsin

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 Wisconsin departing on 2/26. 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 Wisconsin

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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$283
Madison
Madison1 stop$286
Chicago
Chicago1 stop$214
Milwaukee
Milwaukee1 stop$283
Madison
Madison1 stop$286
Chicago
Chicago1 stop$214

Book Cheap Key West to Wisconsin 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 Wisconsin 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 Wisconsin

Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
6:51 pm - 9:06 am
ORD
-
EYW
37h 15m
2 stops
$214Multiple Airlines
Mon, Feb 23 - Mon, Mar 2
Spirit Airlines Logo
2:25 pm - 11:22 am
EYW
-
ORD
21h 57m
1 stop
Spirit Airlines Logo
5:15 am - 1:30 pm
ORD
-
EYW
7h 15m
1 stop
$228Spirit Airlines
Tue, Feb 24 - Tue, Mar 3
Multiple Airlines Logo
1:01 pm - 5:03 pm
EYW
-
ORD
29h 02m
1 stop
Multiple Airlines Logo
10:19 am - 11:50 am
ORD
-
EYW
24h 31m
1 stop
$229Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
6:45 pm - 9:37 pm
EYW
-
ORD
3h 52mnonstop
American Airlines Logo
8:10 am - 12:37 pm
ORD
-
EYW
3h 27mnonstop
$249American 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
7:10 am - 5:44 pm
ORD
-
EYW
9h 34m
1 stop
$269United Airlines
Thu, Apr 16 - Tue, Apr 21
American Airlines Logo
5:42 pm - 11:28 pm
EYW
-
MSN
6h 46m
1 stop
American Airlines Logo
10:05 am - 6:15 pm
MSN
-
EYW
7h 10m
1 stop
$286American Airlines
Fri, Apr 17 - Wed, Apr 22
Delta Logo
7:33 am - 5:49 pm
EYW
-
MSN
11h 16m
2 stops
Delta Logo
11:19 am - 7:40 pm
MSN
-
EYW
7h 21m
1 stop
$346Delta
Thu, Apr 16 - Wed, Apr 22
Delta Logo
1:22 pm - 8:14 pm
EYW
-
MSN
7h 52m
1 stop
Delta Logo
11:19 am - 7:40 pm
MSN
-
EYW
7h 21m
1 stop
$371Delta
Fri, Apr 17 - Wed, Apr 22
Breeze Airways Logo
9:49 am - 9:08 am
EYW
-
MSN
24h 19m
1 stop
Breeze Airways Logo
6:36 pm - 9:06 am
MSN
-
EYW
13h 30m
1 stop
$403Breeze Airways
Booking Insights

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

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

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

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Key West to Wisconsin were found on Spirit Airlines ($228) and American Airlines ($249).

Good to know

Cheapest flight$87
Flight from Key West to Chicago O'Hare Airport

FAQs - booking Wisconsin flights

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

    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 Wisconsin.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Wisconsin 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 Wisconsin?

    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 Wisconsin 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 Wisconsin?

    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 Wisconsin 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 Wisconsin

  • Looking for a cheap flight? 25% of our users found tickets from Key West to the following destinations at these prices or less: Chicago $346 one-way - $413 round-trip

Reviews of the top airlines flying from Key West to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Key West to Wisconsin. 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 Wisconsin? 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.
7.9
DeltaOverall score based on 8124 reviews
7.8Entertainment
7.9Comfort
8.1Boarding
7.2Food
8.5Crew
Airline reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

10.0 ExcellentSteven, Jan 2026
FLL - CVG
Read more Delta reviews

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Food is basically Sun Chips, cookies or Cheezits. I had an exit row seat so I had plenty of room. The crew was very nice and efficient. Pilot kept us informed. Pretty good flight.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The food is terrible. The staff is wonderful. Comfort is good.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

We were upgraded to First Class and it was a great flight

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

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

Information on your arrival and departure airports