Flights from Chicago to Wisconsin

Flight deals from Chicago to Wisconsin

Looking for a cheap last-minute deal or the best return flight from Chicago to Wisconsin? If you want to travel next month, return fares start from $306. Find the lowest prices on one-way and return tickets right here.

Milwaukee.$306 per passenger.Departing Wed, 20 May, returning Thu, 21 May.Return flight with American Airlines.Outbound direct flight with American Airlines departs from Chicago O'Hare International on Wed, 20 May, arriving in Milwaukee General Mitchell.Inbound direct flight with American Airlines departs from Milwaukee General Mitchell on Thu, 21 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $306, select.

Eau Claire.$306 per passenger.Departing Fri, 5 Jun, returning Sun, 7 Jun.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 5 Jun, arriving in Eau Claire.Inbound direct flight with United departs from Eau Claire on Sun, 7 Jun, arriving in Chicago O'Hare International.Price includes taxes and charges.From $306, select.

Rhinelander.$357 per passenger.Departing Fri, 29 May, returning Sun, 31 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 29 May, arriving in Rhinelander.Inbound direct flight with United departs from Rhinelander on Sun, 31 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $357, select.

Green Bay.$403 per passenger.Departing Fri, 14 Aug, returning Sun, 16 Aug.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 14 Aug, arriving in Green Bay.Inbound direct flight with United departs from Green Bay on Sun, 16 Aug, arriving in Chicago O'Hare International.Price includes taxes and charges.From $403, select.

Madison.$403 per passenger.Departing Tue, 19 May, returning Tue, 26 May.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Tue, 19 May, arriving in Madison.Inbound direct flight with United departs from Madison on Tue, 26 May, arriving in Chicago O'Hare International.Price includes taxes and charges.From $403, select.

Appleton.$403 per passenger.Departing Wed, 1 Jul, returning Sun, 5 Jul.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Wed, 1 Jul, arriving in Appleton.Inbound direct flight with United departs from Appleton on Sun, 5 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $403, select.

Wausau.$405 per passenger.Departing Fri, 10 Jul, returning Mon, 13 Jul.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Fri, 10 Jul, arriving in Wausau Central Wisconsin.Inbound direct flight with United departs from Wausau Central Wisconsin on Mon, 13 Jul, arriving in Chicago O'Hare International.Price includes taxes and charges.From $405, select.

La Crosse.$504 per passenger.Departing Thu, 8 Oct, returning Thu, 15 Oct.Return flight with United.Outbound direct flight with United departs from Chicago O'Hare International on Thu, 8 Oct, arriving in La Crosse.Inbound direct flight with United departs from La Crosse on Thu, 15 Oct, arriving in Chicago O'Hare International.Price includes taxes and charges.From $504, select.

Show more deals

Flying from Chicago to Wisconsin

Arm yourself with these facts on the fly.

Cheapest flight found	$306
Cheapest month to fly	May
Average flight time	1 hr, 2 mins
Cheapest airport to fly from	Chicago O'Hare International
Most popular airline	American Airlines

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 $306 and one-way tickets from $145 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 May

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

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 $306 is the best price. This is good, compared to the average Wisconsin ticket price of $386.

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

The cheapest month to fly from Chicago to Madison Airport is usually May. The cheapest month to fly from Chicago to Milwaukee General Mitchell Airport is usually May. The cheapest month to fly from Chicago to Green Bay Airport is usually August. And the cheapest month to fly from Chicago to Eau Claire Airport is usually June.

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 Wednesday, 20 May 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.