Chicago based hunter here. It's so much more expensive to get deer in Illinois... Here's a quick breakdown.
So first off, you want to hunt in Illinois if you're going to. It is way cheaper since out of state permits in Wisconsin are expensive!
Before you get your hunting permit, assuming you were born after 1982 or so, you have to take a hunter's safety course. See this dnr website. They fill up early and are few and far between so sign up now. That's about 16 hours worth of your time right off the bat before you can even go hunting.
Then you have to get a gun. In Illinois, it is illegal to hunt with a rifle so you're looking at a Mossberg 500 or a Remington 380. A 500 will run you around $350 out the door. You also have to buy a blaze orange vest and hat which is around $20 if you cheap out.
Ok, so now you can hunt. To be able to actually harvest a deer you need three things:
A Hunting License ($12.50)
A Habitat Stamp ($5.50)
A Deer tag (Anywhere between $25 and $42.50 depending on tag type. Most are $25)
Then you have to find a place to hunt. We'll assume you're just going to hunt at Starved Rock State Park for free.
I'll also assume you won't buy any gear and that you've got everything covered. (a deer stand will run you $100 or so)
If you butcher your deer yourself, you're looking at right around $420 your first season, $550 or so if you get it processed by a butcher.
Of course, that cost goes down each year since you're not buying a new gun each year.
Just at your permit/license costs, you will spend $43 a year to get one deer. If you get a mature buck (which recently seems like a rarity around our parts) you're looking at a dollar a pound or so.
That seems pretty nice, but then you have to start factoring in other things...
If you rent a property to hunt, that will cost you $200 easily if you find a big group of people to hunt. You may also have to:
Rent a truck
Have the deer butchered because your wife doesn't want a deer carcass in your garage
Buy warmer gear
Buy a deer stand
Target practice
Buy multiple tags
Stay at a hotel hunting weekend
So it may seem like a good idea when just looking at the permit price, but the costs easily start stacking up the more you think about it.