I've ordered things from Blue Havana but have never been there. Seems like a nice store based on my ordering experiences. They have two shop exclusives from RoMa Craft, the Ouroboros and Abaddon.
Below, I took one of my old posts on this topic an added some updates based on the latest info I know. Shoot me a message if you have specific questions.
Iwan Ries and Jack Schwartz are in the heart of downtown. Jack Schwartz is downtown and has an above average selection and is a nice place to visit for a weekday smoke during work hours. Place is open from 7 am - 5 pm M-F. No weekend or late evening hours. Smoking area has a few regular height chairs and a few bar height chairs near the outdoor looking window.
Iwan Ries has a small smoking "room" off to the side of the retail humidor that will seat about 5 people but they also offer a nicer/more comfortable paid smoking experience with their member/pay cigar lounge which costs $15 for a full day pass.
Updown and Biggs Mansion are both about 5 minutes from downtown and within a mile of one another. Updown has a very good selection (TAA member and they carry come boutique brands) but no comfy big chairs to relax in, just a couple/few bar stools and a little standing room. They have a backyard tented area to smoke in but you won't get the comfy cigar lounge feel here.
Biggs is a very cool converted mansion and does have the comfy chairs. Their selection is good and they carry a decent amount of boutique options. Nice out front outdoor smoking area when weather permits. General retail indoor smoking area is not very big but probably holds around 10 people. 2 floor member area is really cool but non member usage cost is steep at $75
Tesa is a cool spot but their humidity seems to generally be suffering (and sticks that have been there for any good period of time may be dry. Selection is not very good but you can usually find a Liga you like (and a couple of other decent options) in the humidor. I generally don't go on Friday or Saturday night as it can be a bit loud (in terms of music and talking) which is not my preferred environment if I'm trying to relax.
Blue Havana is up North (about 10-15 minutes from downtown) and they have a fantastic selection as they carry the most boutique cigars of any cigar lounge in the Chicago area. Their smoking lounge is a converted garage behind the retail location but the layout is pretty good and it makes for a decent lounge. Though you must beware of tobacco taxes everywhere in Chicago, BHs total cost come in higher than other places as they add 47.5% in taxes to the cigar price. Other places may bury some taxes in the price of their cigars but I find BH's total cost per cigar higher than other places.
In the suburbs I like Casa in Countryside...a great spot. Selection and appearance are both very good. I also like the Humidor in Westmont...great layout with an above average selection (not as good as Casa though).