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Going to Chicago for an extended weekend! Any locals here that have recommendations on restaurants/ neighborhoods / or tips?


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Visiting for rich Architecture and Culinary experience!  Architecture building wise, I got that covered.  Thought to ask any locals who are familiar with the city for tips and recommendations regarding places considered a must go/ must avoid (save the don't go to Chicago jokes). Neighborhoods that are great to walk around and get a feel of the city. Or Hidden Gems that tourists miss. Or advice on specific areas to avoid. (I do intend to sketch at some places!)  

Would be cool to go to a speak easy or unique bar/ restaurant experiences.  Especially places with both good food and interior/ architectural design/ vibe.  Would like to walk around beautiful/ interesting neighborhoods while avoiding the bad spots. Also, it seems some of the hottest spots requires reservations 1 month in advance. 

Neighborhood Hit List:  Downtown, Millennial Park, West Loop, River North, Magnificent Mile, and Hyde Park.  Tentatively Oak Park (Frank Lloyd Wright) Neighborhood but not considered a safe neighborhood - may get an architecture walking tour guide or skip it altogether.   Also tentative is the Northalsted /"Boystown" neighborhood since my friend and his partner is LGBTQ+ depending on the safety factor. 

Thank you in advance! 


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