$51 Find Cheap Flights from Chicago 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 Chicago to Wisconsin departing on 12/29. 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 Chicago 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 Chicago to Wisconsin, as well as popular online travel agencies
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Cheap Flights from Chicago to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukeenonstop$179
Madison
Madisonnonstop$179
Green Bay
Green Baynonstop$179
Wausau
Wausaunonstop$341
Rhinelander
Rhinelander1 stop$225
La Crosse
La Crossenonstop$347
Minneapolis
Minneapolisnonstop$91
Duluth
Duluthnonstop$184
Milwaukee
Milwaukeenonstop$179
Madison
Madisonnonstop$179
Green Bay
Green Baynonstop$179
Wausau
Wausaunonstop$341
Rhinelander
Rhinelander1 stop$225
La Crosse
La Crossenonstop$347
Minneapolis
Minneapolisnonstop$91
Duluth
Duluthnonstop$184

Book Cheap Chicago 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 Chicago 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 Chicago to Wisconsin

Thu, Nov 13 - Sun, Nov 16
Sun Country Air Logo
7:40 pm - 9:22 pmORD-MSP
1h 42mnonstop
Sun Country Air Logo
8:54 am - 10:39 amMSP-ORD
1h 45mnonstop
$91Sun Country Air
Find Deal
Thu, Oct 16 - Mon, Oct 20
Sun Country Air Logo
8:21 pm - 10:04 pmORD-MSP
1h 43mnonstop
Sun Country Air Logo
5:00 pm - 6:39 pmMSP-ORD
1h 39mnonstop
$92Sun Country Air
Find Deal
Thu, Sep 25 - Thu, Oct 2
 Logo
5:10 am - 11:30 amORD-MSP
6h 20m1 stop
 Logo
5:06 pm - 6:45 pmMSP-ORD
1h 39mnonstop
Fri, Oct 10 - Fri, Oct 17
Delta Logo
6:08 am - 7:35 amORD-MSP
1h 27mnonstop
Delta Logo
7:50 pm - 9:19 pmMSP-ORD
1h 29mnonstop
$123Delta
Find Deal
Sun, Nov 16 - Sun, Nov 16
United Airlines Logo
7:25 am - 8:54 amORD-MSP
1h 29mnonstop
United Airlines Logo
9:56 am - 11:37 amMSP-ORD
1h 41mnonstop
$124United Airlines
Find Deal
Sat, Nov 15 - Sun, Nov 16
 Logo
7:15 am - 12:14 amORD-MSP
16h 59m1 stop
 Logo
8:54 am - 10:39 amMSP-ORD
1h 45mnonstop
Tue, Sep 23 - Tue, Sep 30
United Airlines Logo
2:18 pm - 3:53 pmORD-MSP
1h 35mnonstop
United Airlines Logo
6:00 am - 7:43 amMSP-ORD
1h 43mnonstop
$130United Airlines
Find Deal
Tue, Sep 23 - Tue, Sep 30
Delta Logo
1:43 pm - 3:28 pmMDW-MSP
1h 45mnonstop
Delta Logo
4:00 pm - 5:35 pmMSP-MDW
1h 35mnonstop
$130Delta
Find Deal
Tue, Sep 23 - Tue, Sep 30
American Airlines Logo
3:34 pm - 5:06 pmORD-MSP
1h 32mnonstop
American Airlines Logo
5:40 am - 7:20 amMSP-ORD
1h 40mnonstop
$132American Airlines
Find Deal
Fri, Nov 14 - Mon, Nov 17
American Airlines Logo
8:06 am - 9:15 amORD-GRB
1h 09mnonstop
American Airlines Logo
9:45 am - 11:03 amGRB-ORD
1h 18mnonstop
$179American Airlines
Find Deal
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?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Wisconsin from Chicago found in the last 72 hours was to Green Bay, at $179 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to Madison (MSN), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $179.

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

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $359, prices are generally cheapest when you fly direct.

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

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

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

Good to know

Low seasonMarch
Cheapest flight$51
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago O'Hare Airport to Minneapolis

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.

  • 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 $239 on average. Morning departures are around 18% cheaper than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally in the evening, which is peak travel time and where the average cost of a ticket is $291.

Reviews of the top airlines flying from Chicago to Wisconsin

 
See real verified KAYAK customer reviews for airlines flying from Chicago 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 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.
7.4
United AirlinesOverall score based on 8945 reviews
7.1Entertainment
8.1Crew
6.6Food
7.7Boarding
7.3Comfort
Airline reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

10.0 ExcellentAnonymous, Aug 2025ORD - MEM
Read more United Airlines reviews

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

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

Cabin class types available on flights to Wisconsin

Cabin classes available on flights to Wisconsin. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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