Although I won't be able to join you, here are a couple places I like.
Prime Cigar Co.
18900 W Bluemound Rd
Brookfield, WI 53045 Map
(262) 754-5220
Havana Lounge & Cigar
9505 W. Greenfield Av
West Allis
414- 258- 8219
Both of these are in western suburbs (not really far at all from Downtown Milwaukee. I have never been to a B&M Downtown, so can't help you there.
There is also this one, but I don't think they serve alcohol. Plus they only had bar stools and not very comfy IMO. If you do a search on Jacks, I think someone did a HERF there a while back... maybe you can PM them.
Jacks Tobacco & McS
13640 W Capitol Dr
Brookfield, WI 53005 Map
(262) 783-7473
Enjoy Milwaukee.. do yourself a favor and have a meal at Karl Ratzsch's Restaurant
It's downtown and it's a great German Restaurant (Willard Scott's fav)
320 E Mason St
Milwaukee, WI 53202 Map
(414) 276-2720