A lot definitely comes down to personal preference. Some like tall boots, light weight trail runners, more "classic" hiking boots, regular sneakers, or even sandals (I don't recommend that last one...)
My preference is actually for a 8" combat / law enforcement style boot (preferably with a side-zip for easy removal). I feel that they provide a good amount of cushioning for comfort, provide excellent ankle support & as a bonus defend the foot and ankle from snake bites & stickers / sticks etc. They are designed for people potentially working on their feet all day and carrying heavy loads / moving large distances in rough terrain. (& no, I have no military background).
Although some of these will be above your price range, others will not. Some good brands are Danner, Bates, Converse, 5.11 Tactical & Rothco (there are others too).
My current pair are a 8" Bates side-zip. All that said, I also have a pair of Danner hiking shoes, which while comfortable enough, usually stay home. Same goes for a pair of North Face trail running shoes.
To add to those recommendations, it should go without saying that you shouldn't attempt a hike of any significant length in footwear that hasn't been broken in yet.
It's also important to recognize that even with the most comfortable seeming most expensive high-tech hiking boot on the market, if it doesn't fit your foot right, your hike won't go well.
Aside from obvious size & width, you also need to determine whether or not your foot pronates or supinates (the tendency of the foot to roll in such a way to place more pressure on the inside or outside of the ball of the foot). If you wear shoes or do not use inserts that properly address this, you will end up with blisters at the pressure point.
I suffered blisters on the ball of my foot because of this when wearing trail running shoes that actually caused my feet to pronate MORE than they would have to begin with...
As to where to buy, I used to live in the Detroit area & recall that at the time Meijers sold a couple models of Bates. Also, there are Red Wing Shoes stores all over the area. I've never had a pair myself (why I didn't mention them above), pretty much anyone will tell you they have an excellent reputation. If you are in the Detroit area, you can also check out Joe's Army Navy (in Pontiac & Royal Oak) if you want to try on some combat boots (they may also stock other hiking boots as well).
There is of course also REI & Dick's Sporting Goods.