$73 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 7/7. 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$259
Rhinelander
Rhinelander1 stop$225
La Crosse
La Crossenonstop$229
Minneapolis
Minneapolis1 stop$107
Duluth
Duluthnonstop$239
Milwaukee
Milwaukeenonstop$181
Madison
Madisonnonstop$239
Green Bay
Green Baynonstop$239
Wausau
Wausaunonstop$259
Rhinelander
Rhinelander1 stop$225
La Crosse
La Crossenonstop$229
Minneapolis
Minneapolis1 stop$107
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

Tue, Jun 16 - Wed, Jun 17
Southwest Logo
5:20 pm - 11:55 pm
MDW
-
MSP
6h 35m
1 stop
Southwest Logo
6:40 pm - 8:10 pm
MSP
-
MDW
1h 30mnonstop
$107Southwest
Tue, May 26 - Tue, Jun 2
Southwest Logo
7:55 am - 9:25 am
MDW
-
MSP
1h 30mnonstop
Southwest Logo
8:40 am - 4:35 pm
MSP
-
MDW
7h 55m
2 stops
$112Southwest
Tue, May 5 - Tue, May 5
Delta Logo
6:25 am - 8:11 am
ORD
-
MSP
1h 46mnonstop
Delta Logo
4:36 pm - 6:13 pm
MSP
-
ORD
1h 37mnonstop
$117Delta
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
$136Sun Country Air
Tue, May 5 - Wed, May 13
Delta Logo
9:29 am - 11:10 am
MDW
-
MSP
1h 41mnonstop
Delta Logo
7:00 am - 8:42 am
MSP
-
MDW
1h 42mnonstop
$137Delta
Thu, May 7 - Sun, May 10
Sun Country Air Logo
8:06 pm - 9:50 pm
ORD
-
MSP
1h 44mnonstop
Sun Country Air Logo
3:35 pm - 5:11 pm
MSP
-
ORD
1h 36mnonstop
$137Sun Country Air
Wed, Apr 29 - Sat, May 2
United Airlines Logo
5:45 pm - 7:23 pm
ORD
-
MSP
1h 38mnonstop
United Airlines Logo
8:00 am - 9:37 am
MSP
-
ORD
1h 37mnonstop
$147United Airlines
Wed, May 6 - Wed, May 13
United Airlines Logo
8:57 pm - 10:03 pm
ORD
-
MKE
1h 06mnonstop
United Airlines Logo
6:00 am - 7:05 am
MKE
-
ORD
1h 05mnonstop
$181United Airlines
Tue, May 26 - Tue, Jun 2
American Airlines Logo
6:40 am - 7:42 am
ORD
-
MKE
1h 02mnonstop
American Airlines Logo
6:08 am - 7:27 am
MKE
-
ORD
1h 19mnonstop
$182American Airlines
Sun, May 10 - Wed, May 13
American Airlines Logo
2:54 pm - 3:56 pm
ORD
-
MKE
1h 02mnonstop
American Airlines Logo
5:06 am - 6:25 am
MKE
-
ORD
1h 19mnonstop
$200American 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 $473.

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 13% more expensive 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 $318.

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 $318, 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 Mondays 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$73
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Chicago Midway Airport to Duluth

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 9574 reviews
6.6Food
7.3Comfort
7.1Entertainment
8.1Crew
7.7Boarding
Airline reviews

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

2.0 MediocreAaron, Apr 2026
ORD - BNA
Read more United Airlines reviews

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!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

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

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

No Snacks or Entertainment. The flight was short, snacks should still be given.

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.