As far as breweries where you can buy their beer at a store my spending goes in this order
Goose Island - Bourbon County and its variants can't be beat, the sours are solid if not a bit overpriced for me now unfortunately and Sofie & Matilda are mainstays in my fridge
Pipeworks - I've really been enjoying their berliners and hoppy beers, Abduction was solid (got a sneak peak last week at the Coffee Break Abduction that is just starting to hit shelves and it was great). I love that they're putting out a wide range of styles of beer.
Revolution - Anti-Hero and Eugene cans are go to beers for me. Cross of Gold is a favorite when it comes to light, easy drinking beer. The barrel aged bottles have been tasty so far.
Half Acre - Daisy Cutter is probably my all-time most consumed beer. I just don't live close enough to anywhere that gets it fresh regularly to buy as much as the others above.
Three Floyds - Availablity and lack of bottle dating push them farther down the list than what my taste buds would like.
Metropolitan - I'm a big fan of the Kolsch, usually get 3 or 4 sixers of it throughout the year.
Two Brothers - Cane & Ebel is the only beer I usually buy from them.
5 Rabbit - Waiting for their brewery to open up so I can revisit their stuff. Had some bad bottles when they first came out.
Finch's - Not a fan of their beer or their marketing
As far as where I like to drink, the order is a bit different
Revolution - The brewpub or the tap room on Kedzie top my list of places that I like to drink at when I get into Chicago. The food at the brewpub is top notch. The beer lists at both places always have something special on tap.
Half Acre - The new tap room is great. I've probably been there 4 or 5 times since it opened.
Two Brothers - Despite not enjoying their beer all that much, it's still a fun place to drink at. The food at the brewpub in Warrenville is solid and the bartenders are great.
Three Floyds - I don't get here much but always have a great time when I do
Goose Clybourn - The beer list is usually pretty pedestrian and I feel the food is overpriced. I love the bar though.
Haymarket - Mathias is a great beer, haven't been enamored with much else I've had (although I haven't had all of their barrel aged beers). Food was pretty mediocre. Usually too crowded for my liking
Piece - Pizza and beer are both solid, but I don't go out of my way to get here
Solemn Oath - I like the space, but it's small and usually crowded. None of their beers have wowed me. They're clean beers, nothing off in them so that's good, but I haven't found anything that I have to go out of my way for.
Flossmoor - I pretty much gave up on this place after the way they got rid of Shimkos and his beers were a pretty big departure from when Matt Van Wyk was there.