re: Chicago for Cubs' game

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Any other good bars? Maybe craft beer focused?

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Go to Tiny Tapp or Corridor before the Cubs game for craft beer. Corridor has completely fallen off since losing multiple brewers to Maplewood and MoRE, but they do have solid food.

Otherwise, check out the standard heavyweight breweries: Hop Butcher, Maplewood, Half Acre, Revolution, Goose Island, and Dovetail.

For an actual craft beer bar / tavern, go to Hopleaf, Union, Bangers & Lace, Bitter Pops, Beermiscuous, Beer Temple, Village Tap, Map Room, Centennial, and Sheffield's. All have craft beer from Chicagoland / Midwest. First three I listed sound like what you're looking for but you also might enjoy Beermiscuous, Beer Temple, and/or Bitter Pops. Incredible can selections with taprooms and draft pours.

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Any recommendations on neighborhoods to stay / Airbnb? What about ones to avoid? Currently looking at a few in Old City

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Guessing you mean Old Town. Just a word of caution that it's an extremely young neighborhood. A lot of kids fresh out of college and Wells is littered with bars that are definitely wilder than what, I assume, 40-somethings are looking for

If you're just going to be in Chicago to drink, enjoy the game, etc., and don't care about anything touristy along Mag Mile and The Loop, find an Airbnb in Lincoln Park, Lake View, Roscoe Village, Lincoln Square, Ravenswood, or Logan Square. Nothing wrong with grabbing a high-rise condo in River North, either, but certainly think your group might have a better experience immersing yourselves in the neighborhoods with bars, breweries, etc.

Logan is one of the top two restaurant neighborhoods in the city right now, and loaded with breweries and cocktail bars. Would say it's slightly less convenient for getting to a Cubs game, so might be worth an Uber over at some point.