$118 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 8/24. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Pensacola to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukee1 stop$239
Madison
Madison1 stop$292
Green Bay
Green Bay1 stop$319
Minneapolis
Minneapolis1 stop$242
Chicago
Chicago1 stop$213
Milwaukee
Milwaukee1 stop$239
Madison
Madison1 stop$292
Green Bay
Green Bay1 stop$319
Minneapolis
Minneapolis1 stop$242
Chicago
Chicago1 stop$213

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

Mon, Aug 24 - Wed, Aug 26
Multiple Airlines Logo
7:32 pm - 12:50 pm
PNS
-
ORD
17h 18m
1 stop
Multiple Airlines Logo
5:59 pm - 3:14 pm
ORD
-
PNS
21h 15m
1 stop
$238Multiple Airlines
Mon, Jul 27 - Tue, Aug 4
Frontier Logo
4:11 pm - 7:58 am
PNS
-
MKE
15h 47m
1 stop
Frontier Logo
8:43 am - 3:46 pm
MKE
-
PNS
7h 03m
1 stop
$239Frontier
Tue, Jul 21 - Wed, Jul 22
Frontier Logo
7:26 pm - 12:21 pm
PNS
-
MSP
16h 55m
1 stop
Frontier Logo
10:15 pm - 6:31 pm
MSP
-
PNS
20h 16m
1 stop
$242Frontier
Fri, Aug 21 - Tue, Aug 25
United Airlines Logo
2:20 pm - 8:56 pm
PNS
-
MSN
6h 36m
1 stop
United Airlines Logo
6:30 am - 1:09 pm
MSN
-
PNS
6h 39m
1 stop
$292United Airlines
Sat, Oct 31 - Sun, Nov 8
United Airlines Logo
2:13 pm - 7:02 pm
PNS
-
MSN
4h 49m
1 stop
United Airlines Logo
5:00 am - 1:53 pm
MSN
-
PNS
8h 53m
2 stops
$297United Airlines
Tue, Nov 3 - Mon, Nov 9
American Airlines Logo
5:59 pm - 11:51 pm
PNS
-
MSN
5h 52m
1 stop
American Airlines Logo
5:00 am - 12:41 pm
MSN
-
PNS
7h 41m
1 stop
$304American Airlines
Fri, Oct 30 - Sun, Nov 8
American Airlines Logo
6:56 pm - 11:31 pm
PNS
-
MSN
4h 35m
1 stop
American Airlines Logo
5:00 am - 12:41 pm
MSN
-
PNS
7h 41m
1 stop
$309American Airlines
Wed, Aug 12 - Tue, Aug 18
Delta Logo
5:00 pm - 11:53 pm
PNS
-
MKE
6h 53m
1 stop
Delta Logo
5:34 am - 12:37 pm
MKE
-
PNS
7h 03m
1 stop
$317Delta
Tue, Jul 21 - Tue, Jul 28
Delta Logo
6:08 pm - 10:48 pm
PNS
-
GRB
4h 40m
1 stop
Delta Logo
5:10 am - 10:51 am
GRB
-
PNS
5h 41m
1 stop
$319Delta
Tue, Jul 21 - Tue, Jul 28
Southwest Logo
2:00 pm - 10:50 pm
PNS
-
MKE
8h 50m
2 stops
Southwest Logo
3:40 pm - 8:00 pm
MKE
-
PNS
4h 20m
1 stop
$322Southwest
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.

How much is a round-trip flight from Pensacola to Wisconsin?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Pensacola to Wisconsin departing in July.

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 September, when tickets cost $124 (return) on average. On the other hand, the most expensive months are May and December, when the average cost of round-trip tickets is $328 and $323 respectively.

Good to know

Low seasonJanuary
Cheapest flight$118
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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.

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 $217 one-way - $393 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.
7.9
SouthwestOverall score based on 4246 reviews
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
8.0Comfort
Airline reviews

Kayak could’ve posted the correct gate number. Almost missed my flight.

8.0 ExcellentValerie, Jun 2026
MCO - ATL
Read more Southwest reviews

Kayak could’ve posted the correct gate number. Almost missed my flight.

Slow boarding, limited food and drink portions. Bad delays and turbulence

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

I liked it better when you were truer to your roots Am paying more for less fun

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Easy to book and to get check in and get on and off.

Five hour delays every hour, I wish it were all at once

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

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.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Wifi did not work and they only served water, coffee, or tea.

It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.

Checking in at the airport the agent only booked the first keg of my trip and had my checked luggage going to the airport with a layover! Never was issued a boarding pass for the second leg or received sticker fir my checked bag. All was well in the end! Delta agents helped to resolve the situation!!!

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

Had assistance at airport getting from arrivals gate to departure gate; I couldn't have managed without that extra help. Thank you Delta.

Horrible I am at almost 2,000,000 miles on United. This was probably the worst flight ever. An hour and a half before takeoff I get a message that they’re changing the plane and I no longer have a seat in Polaris business Supposedly, there was a problem with the plane, but then there was no other plane Finally, they decided to bring a plane from Newark to Washington Dulles Of course the original flight was at 10:45 PM so by the time the plane got there it was 12:30 AM. It had not been cleaned. It had not been catered. They don’t really have people available to do those things when it’s not pre-programmed at 1 o’clock in the morning. The crew had to be changed And the new plane held 28 fewer people than the scheduled plane There is no way you can hate United Airlines enough The people at the gate were actually just fine, but it was management who was completely useless And did they send extra help to the people at the gate? Did they send supervisors? Of course not. Just don’t take United find somebody else or buy a boat

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

The flight had a delay but I made it to my connection. Flight was smooth overall

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

Flights were on time. Free Wifi on plane. Everything was well organized.

Deplaning was delayed because of Jetbridge equipment issues in MKE, causing an issue on an otherwise great flight.

Delays took 2hours and thirty minutes making me miss my connecting flight and make me sit in the Chicago airport for 9 hours

The flight attendant was very kind and offered my son a snack for free.

No real agent onsite helping you for missing luggage there. Not like the other airline next to UA desk, they have staff attending in their desk assisting answer/helping luggage issue, even after midnight.

The wi-fi was awful. I paid $8 each way and got little , except frustration. .

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

there are no options s for snack besides cookies would ve nice to have a salty option n

Never ontime and always delays. Long waits for customer service and often app doesn’t work

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

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

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.

Horrible airline! They always got something messed up with their planes. 3 hour delayed made us missed both out flights. Had to wake up early in the morning next morning to get another flight!

Took off over an hour late with multiple mechanical issues. Gate agent in Dallas was lazy and was slow as molasses. Had a line 10 people long. Spirit bad..

The flight was great until towards the end when the flight attendant read an excessively long commercial for purchasing an american airlines credit card. The worst part is that we are doing a lot of traveling this year so i was actually interested in getting the credit card, but I was so annoyed with the long commercial that I completely dismissed the flight attendant bringing around the information. Next time, keep the sales pitch to 10 seconds and then pass around the brochures!!

Me and my husband experienced very bad in American Airlines. We missed our flight going to Doha. The American Airlines was delayed we arrived already 10:27pm. Supposed to be 9:40 pm. So what they did they rebooked our flight and they gave us a hotel. When we arrived at the hotel the front desk said it was fully booked already. Oh my gosh! I said why did you accept the booking if it's fully booked. The guy said that's American Airlines they just book even it's already full. That's 2am already, we have nothing to do so, we decided to go another hotel. We pay the room, food and taxi. Pls give an action on this matter. Refund our expenses and give us more compensation. Not only our room, food, taxi but also our efforts, tiredness looking for a room that can accommodate us.

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

Information on your arrival and departure airports