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This probably largely due to proximity to me, but La Cantina on Michigan Ave is geeat. Really solid Mexican food and a decent bar area.
Additionally, I looove Duneyrr Fermenta brewery/taproom in Motor Row. They do some really cool, novel stuff, have an awesome space, and the owner's dogs, Moxie and Fez, serve as bouncers and are the absolute best.
Brando's Speakeasy is a bit to the North. Reggie's is a bit to the south.
Brando's is decent, but it's cramped as hell. Can hardly move inside on a busy night.
I'm a big fan of Cafecito.
Tapas Valencia is great for dates. Nepal House for good takeout. Yolk for brunch. Burger Point for a good burger.
Was a much bigger bar neighborhood before covid, used to go to the SLC every weekend.
I do enjoy Kasey's Tavern,which is still open.
I'm not sure where in South Loop you are or what's "walking distance." I'd say Asian Outpost is my favorite spot. Yolk for breakfast, and I really like Niu B but was only there once or twice. Probably not walkable but La Cantina has good food as well.