$86 Find Cheap Flights from Chicago to Wisconsin - Compare and Save

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Cheap Flights from Chicago to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Milwaukee
Milwaukeenonstop$171
Madison
Madisonnonstop$309
Green Bay
Green Baynonstop$309
Wausau
Wausaunonstop$282
La Crosse
La Crossenonstop$285
Rhinelander
Rhinelander1 stop$265
Minneapolis
Minneapolisnonstop$123
Duluth
Duluthnonstop$309
Milwaukee
Milwaukeenonstop$171
Madison
Madisonnonstop$309
Green Bay
Green Baynonstop$309
Wausau
Wausaunonstop$282
La Crosse
La Crossenonstop$285
Rhinelander
Rhinelander1 stop$265
Minneapolis
Minneapolisnonstop$123
Duluth
Duluthnonstop$309
Booking Insights

KAYAK's insights & trends for Chicago to Wisconsin flights

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

What is the cheapest Chicago to Wisconsin flight route?

The cheapest ticket to Wisconsin from Chicago found in the last 5 days was to Eau Claire, at $180 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Green Bay (GRB), and the cheapest round-trip airline ticket found on this route in the last 5 days was $269.

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 $179 on average. Morning departures are around 43% 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 $320.

Can I save money by flying with a layover from Chicago to Wisconsin?

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $487 on average.

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

The cheapest month for flights from Chicago to Wisconsin is January, when tickets cost $254 (return) on average. On the other hand, the most expensive months are October and April, when the average cost of round-trip tickets is $533 and $524 respectively.

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

If you are looking for a flight deal from Chicago to Wisconsin, look for departures on Thursdays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Wisconsin, Wednesday is the cheapest day to fly and Sunday is the most expensive.

Good to know

Low season

January

Cheapest flight

$86
Best time to beat the crowds with an average 37% drop in price.
Most popular time to fly and prices are also 6% lower on average.
Flight from Chicago O'Hare Airport to Milwaukee

FAQs - booking Wisconsin flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago 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 Chicago 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 Chicago 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 Chicago 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 Chicago to Wisconsin up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Wisconsin

 
Need help choosing which airline to fly with from Chicago 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.
7.3
United AirlinesOverall score based on 10432 reviews
7.1Entertainment
6.7Food
8.1Crew
7.3Comfort
7.7Boarding
Airline reviews

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

4.0 Okay72Yonatan, Oct 2026
Read more United Airlines reviews

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Price was crazy watch it if you Chan he your flight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

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

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

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

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

More options for your flight from Chicago to Wisconsin

Complete your trip to Wisconsin with a hotel stay or car rental