I am planning a trip from Chicago to south-west SD. Taking the family to the Black Hills, Rushmore, Badlands, Custer, etc... I am looking for suggestions for breweries, restaurants and liquor stores to visit there or on the way. Let me know, Thanks.
Riley's Madison is a good liquor store, great Dane is a great brewpub in Madison, other than that nothing horribly significant right off of I-90. If are willing to spend a half a day or so new ulm is just shy of an hour north of the interstate and is a neat little town that loves their German heritage and home to the best brewery in the Midwest(architecturally). I would recommend trying to get there late afternoon of day one get some supper explore the town town and visit the brewery after breakfast on the second day. This would be an option for Decorah with toppling Goliath as well but that might be a tad further from the highway. But if you are trying to stay on the highway Minnesota hasn't got much for you
About 20 mins south of I-90/Albert Lea is Worth Brewing in Northwood, IA. If you can schedule a stop around very limited hours they have some good offerings. I believe they have 1919 root beer on tap for the kiddies too.
Firehouse Brewpub in Rapid City, SD had good food and decent beer last time I was there. A few breweries have opened up in the Black Hills in the last few years but I haven't been there recently. As ben mentions above, the August Schell Brewery in New Ulm, MN is historic and a nice stop but is not on an interstate highway so could be a bit out of your way.
Woodmen's in lacrosse/onalaska is convenient place with as good of sharing as you will find in lacrosse. If you want surly, what's crossroads in Rochester would probably be your best bet, but a couple of miles off the road. If you are that far onto Rochester I would recommend Rosco's for a bite to eat. They don't serve any beer but they are quick and really the only local food worth mentioning in Rochester (IMO)