Flights from Chicago to Wisconsin

Flight deals from Chicago to Wisconsin

Looking for cheap tickets from Chicago to Wisconsin, or a last-minute trip? Find the lowest prices on one-way and return tickets right here.

Milwaukee.P10,519 per passenger.Departing Fri, 30 Jan, returning Sun, 1 Feb.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 30 Jan, arriving in Milwaukee General Mitchell.Inbound direct flight with United departs from Milwaukee General Mitchell on Sun, 1 Feb, arriving in Chicago O'Hare International.Price includes taxes and charges.From P10,519, select.

Madison.P10,526 per passenger.Departing Fri, 1 May, returning Mon, 4 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 1 May, arriving in Madison.Inbound direct flight with United departs from Madison on Mon, 4 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From P10,526, select.

Green Bay.P11,400 per passenger.Departing Sat, 7 Mar, returning Sun, 15 Mar.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Sat, 7 Mar, arriving in Green Bay.Inbound direct flight with United departs from Green Bay on Sun, 15 Mar, arriving in Chicago O'Hare International.Price includes taxes and charges.From P11,400, select.

Appleton.P11,400 per passenger.Departing Fri, 16 Jan, returning Sat, 24 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 16 Jan, arriving in Appleton.Inbound direct flight with United departs from Appleton on Sat, 24 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From P11,400, select.

Eau Claire.P13,510 per passenger.Departing Fri, 16 Jan, returning Sun, 18 Jan.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 16 Jan, arriving in Eau Claire.Inbound direct flight with United departs from Eau Claire on Sun, 18 Jan, arriving in Chicago O'Hare International.Price includes taxes and charges.From P13,510, select.

Rhinelander.P18,055 per passenger.Departing Sat, 4 Jul, returning Sat, 11 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 4 Jul, arriving in Rhinelander.Inbound indirect flight with Delta, departs from Rhinelander on Sat, 11 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From P18,055, select.

Wausau.P21,088 per passenger.Departing Wed, 13 May, returning Wed, 20 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 13 May, arriving in Wausau Central Wisconsin.Inbound indirect flight with Delta, departs from Wausau Central Wisconsin on Wed, 20 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From P21,088, select.

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Flying from Chicago to Wisconsin

Arm yourself with these facts on the fly.

Cheapest flight found	P10,519
Cheapest month to fly	January
Average flight time	1 hr, 1 min
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	United

How to find cheap flights from Chicago to Wisconsin

We've compared the best online travel agents and flight providers on the internet to find the cheapest plane tickets from Chicago to Wisconsin. Other savvy travellers recently found return flights from P10,519 and one-way tickets from P5,152 one-way. Ready to join them? Here are a few tips to help you do it the smart way.

Fly from Chicago O'Hare International into Milwaukee General Mitchell

At the moment, the lowest priced flight tickets to Wisconsin are from Chicago O'Hare International Airport to Milwaukee General Mitchell Airport.

Fly in January

We crunched the flight calendar and found the cheapest time to fly from Chicago to Wisconsin is currently January.

Flex your dates for the best rates

If you’re flexible on your departure dates, you can use Skyscanner's whole month tool to find the cheapest day of the year to fly from Chicago to anywhere you choose in Wisconsin.

Watch as fares rise and fall

With Price Alerts, we'll let you know when flight prices from Chicago to Wisconsin go up or down so you can book when the time is just right.

Relax – these are fee-free flight tickets

With us, there are no added fees – the Wisconsin to Wisconsin flight price you see when you search with us is what you pay to the provider.

Frequently asked questions

What's the average Chicago to Wisconsin flight price?

We looked at all of the upcoming return flights from Chicago to Wisconsin we could find over the next 12 months. It looks like P10,519 is the best price. This is good, compared to the average Wisconsin ticket price of P13,785.

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

The cheapest month to fly from Chicago to Rhinelander Airport is usually July. The cheapest month to fly from Chicago to Wausau Central Wisconsin Airport is usually May. The cheapest month to fly from Chicago to Madison Airport is usually May. And the cheapest month to fly from Chicago to Milwaukee General Mitchell Airport is usually January.

Which upcoming date is cheapest to fly from Chicago to Wisconsin on?

After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Chicago to Wisconsin on Friday, 30 January 2026.

Are there any direct flights from Chicago to Wisconsin?

Chicago O'Hare International Airport offers direct flights to Wisconsin.

If I'm flying from Chicago, where in Wisconsin is cheapest to fly into?

If you're flying from Chicago, the cheapest city in Wisconsin to fly into is Milwaukee. The cheapest airport serving Milwaukee at the moment is Milwaukee General Mitchell.