$79 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 7/22. 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 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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Flight Deals

Cheap Flights from Chicago to Wisconsin

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Milwaukee
Milwaukeenonstop$181
Madison
Madisonnonstop$239
Green Bay
Green Baynonstop$239
Wausau
Wausaunonstop$239
La Crosse
La Crossenonstop$229
Rhinelander
Rhinelandernonstop$210
Minneapolis
Minneapolisnonstop$137
Duluth
Duluthnonstop$239
Milwaukee
Milwaukeenonstop$181
Madison
Madisonnonstop$239
Green Bay
Green Baynonstop$239
Wausau
Wausaunonstop$239
La Crosse
La Crossenonstop$229
Rhinelander
Rhinelandernonstop$210
Minneapolis
Minneapolisnonstop$137
Duluth
Duluthnonstop$239

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

Wed, Jun 17 - Wed, Jun 24
Delta Logo
12:27 pm - 2:09 pm
ORD
-
MSP
1h 42mnonstop
Delta Logo
7:00 am - 8:35 am
MSP
-
ORD
1h 35mnonstop
$137Delta
Wed, Jun 17 - Tue, Jun 23
Southwest Logo
7:40 am - 9:10 am
MDW
-
MSP
1h 30mnonstop
Southwest Logo
3:50 pm - 5:20 pm
MSP
-
MDW
1h 30mnonstop
$137Southwest
Sat, May 16 - Mon, May 18
Multiple Airlines Logo
6:55 am - 1:37 pm
ORD
-
MSP
6h 42m
1 stop
Multiple Airlines Logo
5:30 pm - 7:06 pm
MSP
-
ORD
1h 36mnonstop
$144Multiple Airlines
Thu, May 14 - Mon, May 18
Sun Country Air Logo
8:00 am - 9:44 am
ORD
-
MSP
1h 44mnonstop
Sun Country Air Logo
5:30 pm - 7:06 pm
MSP
-
ORD
1h 36mnonstop
$147Sun Country Air
Thu, May 14 - Mon, May 18
Sun Country Air Logo
8:00 am - 9:44 am
ORD
-
MSP
1h 44mnonstop
Sun Country Air Logo
5:30 pm - 7:06 pm
MSP
-
ORD
1h 36mnonstop
$148Sun Country Air
Sat, May 16 - Mon, May 18
Multiple Airlines Logo
9:37 pm - 9:19 am
ORD
-
MSP
11h 42m
1 stop
Multiple Airlines Logo
5:30 pm - 7:06 pm
MSP
-
ORD
1h 36mnonstop
$152Multiple Airlines
Tue, May 19 - Tue, May 19
American Airlines Logo
9:40 am - 10:43 am
ORD
-
MKE
1h 03mnonstop
American Airlines Logo
6:40 pm - 8:05 pm
MKE
-
ORD
1h 25mnonstop
$181American Airlines
Tue, Jun 23 - Tue, Jun 30
American Airlines Logo
8:00 pm - 9:05 pm
ORD
-
MKE
1h 05mnonstop
American Airlines Logo
5:00 am - 6:12 am
MKE
-
ORD
1h 12mnonstop
$185American Airlines
Mon, May 25 - Mon, Jun 1
United Airlines Logo
7:50 pm - 8:56 pm
ORD
-
MKE
1h 06mnonstop
United Airlines Logo
10:38 am - 11:48 am
MKE
-
ORD
1h 10mnonstop
$201United Airlines
Thu, May 21 - Sun, May 31
United Airlines Logo
11:25 am - 12:48 pm
ORD
-
RHI
1h 23mnonstop
United Airlines Logo
1:23 pm - 2:59 pm
RHI
-
ORD
1h 36mnonstop
$210United Airlines
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 Milwaukee, at $171 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 $449.

What is the cheapest time of day to fly to Wisconsin?

The average price for all round-trip flights from Chicago to Wisconsin depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

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 16% cheaper than evening flights, on average. The most expensive time of day to fly to Wisconsin is generally in the afternoon, 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?

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 $348, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago 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 Chicago to Wisconsin is May, when tickets cost $100 (return) on average. On the other hand, the most expensive months are November and April, when the average cost of round-trip tickets is $224 and $200 respectively.

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 Fridays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Wisconsin, Friday is the cheapest day to fly and Sunday is the most expensive.

Good to know

Low seasonJanuary
Cheapest flight$79
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 3% 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.

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 9680 reviews
7.1Entertainment
8.1Crew
7.3Comfort
6.6Food
7.7Boarding
Airline reviews

A long delay. Don't travel late in the day.

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

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.