I am going to be in Chicago for a weekend and I am looking to pick up some nice Bourbon. Coming from Toronto Canada our selection is limited and taxes are high. How are liquor sales handled in Illinois? Is there a store that has a good selection or are there State stores that carry about the same thing? Here in Ontario our liquor stores are run by the province so they all have pretty much the same assortment, Maker's Mark, Wild Turkey, Bullet...
Does anyone have any suggestions for a brand to pick up?
In the States, each state can set up their own rules regarding liquor. Illinois is relatively liberal -- convenience stores, grocery stores, liquor stores, etc. can all sell beer/wine/liquor. I believe alcohol may incur an additional tax but it's small relative to Chicago's standard tax rate of (roughly) 10%. A 750mL bottle of Makers, for example, will retail for ~$25 -- but be prepared to add an additional 10% to cover assorted taxes.
Binny's, as suggested by weinstein5, is a good destination -- Binny's is the local chain of liquor superstores and each location has a very good selection, though it should be said that some locations have a better selection than others. Depending on where you're staying (city, suburbs, etc), you have a few options, and you can see via their website which is most convenient to you -- South Loop, River North and Lincoln Park, if you're in the Downtown areas. Of those three, I think that the Lincoln Park location will have the best selection. Customer service is generally good at all Binnys', though if you're at the Lincoln Park location, ask for David -- he really knows his whiskey. All three are easily accessibly via public transit or taxi. Other city locations are, too, and for suburban locations... it depends.
Two other liquor stores that are worth mentioning are Warehouse Liquors and West Lakeview Liquors. The former is just south of the Loop and has an incredible selection of whiskies in the city. Prices might be a few dollars more than at Bnny's, but they will more likely carry bottles you can't find elsewhere. For example, if you're looking for something really specific (ie. William Larue Weller Antique Selection as opposed to the George Stagg, etc etc), West Lakeview or Warehouse Liquors may have what you want. And about Warehouse Liquors, they are rather more removed from the central downtown area but the customer service is absolutely amazing. They also have a whiskey under the label Willet that's just amazing.
As for brands... that is certainly a personal call. At this point, I doubt you'll find anything with from Pappy Van Winkle (limited allocations -- they sold very quickly at any store lucky enough to get bottles). I think WL Weller is a great label -- WL Weller and Van Winkle are both brands owned and produced by Buffalo Trace these days so, strictly speaking, it's the same liquid but with different age statements and labels. The WL Weller 12yr. is phenomenal and is widely available (it retails for ~$28) -- this is compared to the Pappy Van Winkle 15yr. which retails for ~$50. There's also a WL Weller 107 Antique that's affordable, though I find it just too damn hot to be worthwhile. Barton's is good, across several proofs/price points. I've only seen this at the Lincoln Park Binny's but the Heaven Hill Bottled-in-Bond 100 proof (Gold label) is an amazing whiskey, especially given the price ($13). Four Roses has a huge number of bottles available, at wildly different price points and flavor profiles, too. Really, it comes down to what you like: a wheated bourbon, a rye bourbon... something spicy or something smooth...
There are a few local distillers, too, but... but I wouldn't bother. I see them more of a novelty these days than anything else. Having said that, if you see a bottle of Few Spirits' Rye... it's really good. Not sure if it's worth the price tag (~$65) but it would make for one hell of a special souvenir. Koval is a label that you mist see if you're looking at locals... I'd pass, though their liquers are really good.
You didn't ask about where to drink bourbon in this city, but... but if you want to try a few things before buying, here are some ideas:
Big Star -- located in Wicker Park, this is an amazing bar for people watching, taco eating and bourbon drinking. They have one of the best lists of American whiskies in the city and prices are very reasonable. Expect a lively crowd, pretty good bar food (which is limited to tacos, tostadas, etc -- albeit generally well executed!), and a record player with great musical selections. And, it should be said, if you go at peak times, expect a long wait, too.
Longman & Eagle -- located in Logan Square, this is a restaurant/B&B with a very lively bar area, too. They have a Michelin star and do well with smaller plates. Not quite small plates, like at a tapas bar, but... but not necessarily big, either (that's not necessarily helpful). Expect a crowded, raucous vibe, but, also, a lot of whiskies.
Clark Street Ale House -- located in River North, this is a bar (no food) with a great craft beer selection and a strong whiskey selection, too. I think they focus a little more on Scotch whisky, but the Bourbon selections are good, too.
Sable -- also in River North, this place straddles the line (I think) between restaurant and bar. Looking at the bar first, expect a huge list of cocktails and liquors -- they have one of the bets cocktail programs in the city; food-wise, it's very American Contemporary, and they offer most/all dishes in smaller, half-plate options. It's easy to go and have a complete, full, enjoyable meal -- though I still think of it as a place to go after work and have a small bite or two (or three, if it was a bad day!) along with my cocktail (or two or three... or four if it was a bad day!).
Delilah's on Lincoln has a great whiskey selection. They claim to have 400 different whiskeys and have a $2 or $3 bourbon special every day. I've also been impressed with the selection at The Twisted Spoke (although the pricing can be a bit high). The Twisted Spoke also has an excellent beer list including some rare vintage or hard to find beers (often at high prices). Both of these places are on site consumption only.
2771 N. Lincoln
The Twisted Spoke
501 N. Ogden
I grew up in detroit, so know the run for the duty free at the border well. Don't forget there are limits on what you can bring back in. Canada back to US was one litre per trip and if they catch you they can take it away, but usually just make you pay the duty which jacks up the price above what you could get home,
I'm a big bourbon drinker so I would suggest Blantons or if you're looking for a mixing bourbon, Basil Hayden's Whiskey (only 80 proof).