Smokey Bear is the best cigar shop on this side of town, highly recommended for those on the south side of Chicago. The star is its huge selection of cigars, which is second to none and on par with the best in the city. They carry a number of brands with great depth and have cigars no one else has. Pricing is ok, with several sticks being a good deal and reasonable, though several others are on the high side. The staff is great, very cordial, helpful, kind, and accommodating.
The sit-down lounge isn't big, but it's cozy and comfortable with very nice new renovations and comfortable seating. The atmosphere is super chill, like a man cave away from home. They have a number of TVs to keep you entertained. To sit in the lounge, you must purchase two sticks. They have water and soft drinks, and it is BYOB for alcohol. They also host tons of awesome events. It's a great place to check out and tell a friend about.