$85 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 2/23. 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

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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
Milwaukee2 stops$354
Madison
Madison1 stop$480
Chicago
Chicago2 stops$221
Milwaukee
Milwaukee2 stops$354
Madison
Madison1 stop$480
Chicago
Chicago2 stops$221

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

Wed, Jan 21 - Mon, Jan 26
Multiple Airlines Logo
10:49 am - 10:36 pm
EYW
-
ORD
36h 47m2 stops
Multiple Airlines Logo
5:15 am - 1:30 pm
ORD
-
EYW
7h 15m1 stop
$221Multiple Airlines
Wed, Jan 21 - Mon, Jan 26
Multiple Airlines Logo
10:49 am - 4:58 pm
EYW
-
ORD
7h 09m1 stop
Multiple Airlines Logo
5:15 am - 1:30 pm
ORD
-
EYW
7h 15m1 stop
$226Multiple Airlines
Thu, Apr 9 - Mon, Apr 13
American Airlines Logo
6:39 pm - 9:20 pm
EYW
-
ORD
3h 41mnonstop
American Airlines Logo
8:00 am - 12:16 pm
ORD
-
EYW
3h 16mnonstop
$249American Airlines
Mon, Dec 29 - Mon, Jan 12
American Airlines Logo
1:15 pm - 3:50 pm
EYW
-
ORD
3h 35mnonstop
American Airlines Logo
8:14 am - 12:45 pm
ORD
-
EYW
3h 31mnonstop
$279American Airlines
Mon, Dec 29 - Mon, Jan 12
American Airlines Logo
1:46 pm - 7:44 pm
EYW
-
ORD
6h 58m1 stop
American Airlines Logo
8:14 am - 12:45 pm
ORD
-
EYW
3h 31mnonstop
$289American Airlines
Mon, Dec 29 - Mon, Jan 12
Delta Logo
4:25 pm - 9:14 pm
EYW
-
ORD
5h 49m1 stop
Delta Logo
7:05 am - 1:48 pm
ORD
-
EYW
5h 43m1 stop
$299Delta
Wed, Jan 21 - Thu, Jan 29
American Airlines Logo
4:01 pm - 6:45 pm
EYW
-
ORD
3h 44mnonstop
American Airlines Logo
3:21 pm - 9:47 pm
ORD
-
EYW
5h 26m1 stop
$307American Airlines
Fri, Dec 26 - Tue, Dec 30
United Airlines Logo
12:22 pm - 3:07 pm
EYW
-
ORD
3h 45mnonstop
United Airlines Logo
7:55 am - 12:34 pm
ORD
-
EYW
3h 39mnonstop
$309United Airlines
Wed, Jan 21 - Mon, Jan 26
American Airlines Logo
4:01 pm - 6:45 pm
EYW
-
ORD
3h 44mnonstop
American Airlines Logo
10:59 am - 3:25 pm
ORD
-
EYW
3h 26mnonstop
$315American Airlines
Thu, Jan 8 - Sun, Jan 11
United Airlines Logo
2:25 pm - 10:56 pm
EYW
-
MKE
9h 31m2 stops
United Airlines Logo
8:33 am - 3:17 pm
MKE
-
EYW
5h 44m1 stop
$354United Airlines
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.

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

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

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

Good to know

Cheapest flight$85
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.

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

    The cheapest time of day to fly to Wisconsin is generally in the morning, when round-trip flights cost $377 on average. The most expensive time of day to fly to Wisconsin is generally in the morning, which is peak travel time and where the average cost of a ticket is $377.

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 $270 one-way - $294 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 8007 reviews
8.1Boarding
7.3Food
7.9Comfort
8.5Crew
7.9Entertainment
Airline reviews

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

10.0 ExcellentRonda, Dec 2025
JAX - JFK
Read more Delta reviews

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.

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Non stop on long haul is the way to go. Great experience

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

Really low quality food especially for an international flight. The crew also was surprisingly unpleasant except couple of ladies. I know we were not in first class but that’s no reason to treat customers as less.

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.

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so didn't have any food

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

We loved the steward on the plane. He made the night enjoyable

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

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

Information on your arrival and departure airports