$169 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 1/14. 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 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$269
Madison
Madison1 stop$269
Chicago
Chicago1 stop$269
Minneapolis
Minneapolis1 stop$334
Milwaukee
Milwaukee1 stop$269
Madison
Madison1 stop$269
Chicago
Chicago1 stop$269
Minneapolis
Minneapolis1 stop$334

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, Aug 13 - Wed, Aug 20
Delta Logo
2:00 pm - 8:31 pmEYW-MKE
7h 31m1 stop
Delta Logo
12:15 pm - 8:12 pmMKE-EYW
6h 57m1 stop
$269Delta
Find Deal
Wed, Aug 20 - Mon, Sep 1
Delta Logo
6:22 pm - 10:48 pmEYW-MSN
5h 26m1 stop
Delta Logo
5:40 am - 1:05 pmMSN-EYW
6h 25m1 stop
$269Delta
Find Deal
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
Find Deal
Wed, Aug 13 - Wed, Aug 20
American Airlines Logo
5:55 pm - 11:04 pmEYW-MKE
6h 09m1 stop
American Airlines Logo
6:00 am - 7:07 pmMKE-EYW
12h 07m2 stops
$274American Airlines
Find Deal
Wed, Aug 13 - Wed, Aug 20
American Airlines Logo
1:52 pm - 11:26 pmEYW-MKE
10h 34m2 stops
American Airlines Logo
6:32 am - 7:07 pmMKE-EYW
11h 35m2 stops
$279American Airlines
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
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
Find Deal
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 - Mon, Sep 8
United Airlines Logo
3:50 pm - 11:00 pmEYW-MSP
8h 10m1 stop
United Airlines Logo
6:00 am - 2:55 pmMSP-EYW
7h 55m1 stop
$334United Airlines
Find Deal
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
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

Low seasonJune
Cheapest flight$169
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Key West to Milwaukee

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 $305 one-way - $415 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.
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.

Very poor delay in dfw was really bad n long

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

I didn't like that my paid for seat was changed 2 hours before my flight.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

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

Flight was late and missed connecting flight. They could have better accommodated, but instead did an overnight and had to arrive the next afternoon.

The boarding crew was incredibly helpful getting me on an earlier flight

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

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