$55 Find Cheap Flights from Pensacola 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 Pensacola to Wisconsin departing on 11/17. 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 Wisconsin

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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$324
Madison
Madison1 stop$249
Green Bay
Green Bay2 stops$319
Chicago
Chicagononstop$209
Milwaukee
Milwaukee1 stop$324
Madison
Madison1 stop$249
Green Bay
Green Bay2 stops$319
Chicago
Chicagononstop$209

Book Cheap Pensacola 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 Pensacola 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 Pensacola to Wisconsin

Wed, Dec 3 - Sun, Dec 14
United Airlines Logo
2:15 pm - 4:47 pmPNS-ORD
2h 32mnonstop
United Airlines Logo
10:50 am - 1:16 pmORD-PNS
2h 26mnonstop
$209United Airlines
Find Deal
Thu, Jan 8 - Mon, Jan 12
Multiple Airlines Logo
6:49 pm - 2:19 pmPNS-ORD
19h 30m1 stop
Multiple Airlines Logo
6:11 pm - 10:38 amORD-PNS
40h 27m2 stops
$212Multiple Airlines
Find Deal
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
1:16 pm - 3:55 pmPNS-ORD
2h 39mnonstop
American Airlines Logo
8:25 am - 10:47 amORD-PNS
2h 22mnonstop
$213American Airlines
Find Deal
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
1:16 pm - 3:55 pmPNS-ORD
2h 39mnonstop
American Airlines Logo
8:25 am - 10:47 amORD-PNS
2h 22mnonstop
$214American Airlines
Find Deal
Wed, Nov 12 - Thu, Nov 20
Spirit Airlines Logo
8:16 pm - 11:12 amPNS-ORD
14h 56m1 stop
Spirit Airlines Logo
10:12 am - 7:11 pmORD-PNS
8h 59m1 stop
$218Spirit Airlines
Find Deal
Fri, Feb 6 - Mon, Feb 9
Spirit Airlines Logo
6:49 pm - 3:55 pmPNS-ORD
21h 06m2 stops
Spirit Airlines Logo
5:05 am - 3:36 pmORD-PNS
10h 31m1 stop
$228Spirit Airlines
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Mon, Nov 24 - Sat, Nov 29
Delta Logo
7:09 pm - 12:02 amPNS-ORD
4h 53m1 stop
Delta Logo
5:23 am - 10:41 amORD-PNS
5h 18m1 stop
$229Delta
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Fri, Dec 19 - Mon, Jan 5
Delta Logo
7:15 am - 12:10 pmPNS-ORD
4h 55m1 stop
Delta Logo
8:00 am - 1:53 pmORD-PNS
5h 53m1 stop
$250Delta
Find Deal
Wed, Nov 26 - Mon, Dec 1
Southwest Logo
8:30 pm - 12:30 amPNS-MKE
4h 00m1 stop
Southwest Logo
5:00 am - 9:10 amMKE-PNS
4h 10m1 stop
$352Southwest
Find Deal
Fri, Dec 5 - Sun, Dec 7
Southwest Logo
4:15 pm - 8:15 pmPNS-MKE
4h 00m1 stop
Southwest Logo
5:00 am - 9:10 amMKE-PNS
4h 10m1 stop
$377Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Pensacola to Wisconsin flights

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

What is the cheapest month to fly from Pensacola to Wisconsin?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Wisconsin, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Pensacola to Wisconsin is April, when tickets cost $145 (return) on average. On the other hand, the most expensive months are June and July, when the average cost of round-trip tickets is $442 and $406 respectively.

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

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

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

Good to know

Low seasonApril
Cheapest flight$55
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Pensacola to Chicago O'Hare Airport

FAQs - booking Wisconsin flights

  • How does KAYAK find such low prices on flights from Pensacola 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 Pensacola to Wisconsin.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pensacola 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 Pensacola 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 Pensacola 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 Pensacola 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 Pensacola 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 at night, when round-trip flights cost $329 on average. Morning departures are around 6% more expensive than evening flights, 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 $398.

Top tips for finding cheap flights to Wisconsin

  • Looking for a cheap flight? 25% of our users found tickets from Pensacola to the following destinations at these prices or less: Chicago $125 one-way - $258 round-trip

Reviews of the top 4 airlines serving from Pensacola to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Pensacola 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 Pensacola 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
SouthwestOverall score based on 4243 reviews
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

6.0 GoodDavid, Aug 2025MCO - DEN
Read more Southwest reviews

Near 4 hour flight with only 1 service. Had to use call button to request water. Internet and power not working until into flight. Internet would stop working during flight.

My flight was delayed 50 minutes and we were rushed to board to then sit for 15 minutes until the pilot arrived. Unacceptable since we could have waited to board. Also the delayed flight was updated AFTER we boarded to more than the 10 minutes as originally stated.

If we are going to have to pay for luggage, make it easier to do. Put something on the app during check-in so I don't need to do it at the kiosk. I've done it twice recently and I ended up having to pay at the desk because something went wrong at the kiosk in Tampa.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

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.

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.

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

American airlines suck they delay the flights all the time made me sleep in an airport because my flight was delayed and I miss my connecting flight

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

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.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

Plastic seat really hurt my back. Cannot even recline on the flight. Very hard to sleep on the plane due to terrible seats . Food and drinks were expensive and not very good. There were like 2 open exit rows behind me. My isle was full so I asked flight attendants if I could sit there. They told me it was a safety issue??? I think it more unsafe to have no one sitting there. In case of emergency, you’d want someone there to help.

Had to deplane for undisclosed mechanical issue. Landed in Chicago 3 hours late. Food voucher at FLL came just as we were recording. Crew and agents were troopers--better than Spirit last night.

It was delayed, and the airport had cockroaches jumping on our bags. The flight crew was great, the seats were pretty comfortable.

We spent 5 1/2 hours at Ohare cause our flight was diverted cause of rain in the area. We missed appts that we had set on Tuesday and cause we were flying back the next day on the 7am flight we had no time to reschedule anything. Other airlines were landing and taking off fine having no issues. It was only Spirit. Very frustrating flight and I understand why the flights are only around 25-30% full.

Flight was canceled without warning, gave credit that is hard to access. Awful airline.

I never made my flight because of their poor service, as I said in my other review: I never made this flight. When I got to the airport I had a message to say that the flight was delayed and would be getting into Fort Lauderdale at 10 pm. My connecting flight was due to leave around 10:10 pm so there is no way I would have made the connection. I went back to the Spirit desk and tried to explain this to a desk agent who didn't understand. Eventually her supervisor came over and explained it. The desk agent was unhelpful and only offered options that would have required getting a hotel overnight. She offered no hotel or meal vouchers and when I said that it seemed my only option was to go to another airline she told me I needed to make a decision because they were closing the desk and would not be back till 3 pm. I went to Delta and had to pay extra but they could help get me back to Orlando. I now have to file a claim against Spirit and I am just glad I paid for insurance. Very unhappy and very poor service.

Changing the flight time to 6:15 am on the return flight is extremely inconvenient. The flight was okay. It was on time. The crew was friendly. The seats were uncomfortable. All the upsells are annoying, and I would prefer paying a single higher fee and not have to purchase so much extra.

The flight was delayed twice with minimal explanation. The terminal and airplane were filthy. The food voucher didn’t even cover a tiny pizza from a kiosk in the terminal. All in all, a pretty miserable experience for a flight to attend a funeral

Everything you need to know for your flight from Pensacola to Wisconsin

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