Will look for means of communication off the platform because I would prefer not to advertise where it is I typically stay for my safety.
I don't know if you have ever been to Chicago before but my first day in every city I travel is always spent downtown where I will traverse it and get to know the "climate." I stayed in area called River North and I can be more specific about the hotel privately. I walked down to Navy Pier which was quite a hike but got a feel for the city and topped off with Chicago deep dish pizza!! After that, I find suburbs to stay in every subsequent trip. Where would you like me to send the information I stay and do you stay in a particular star level? My personal is typically 3.5 stars or higher. If staying in higher-level hotels I would not know what to recommend. There is quite a bit of shopping in both Oak Brook and Schaumburg and they are fairly affluent areas. Let me know.
River North has been becoming a high-crime area lately. Things like carjackings, muggings, and robberies are becoming scarily frequent. So it's unsurprising that many hobbyists are gun-shy about venturing there. Especially if they're married, drive there for sexy time, AND get carjacked---how do they explain THAT to their wives? I have plausible deniability, since I work downtown--plus I'm single---but many hobbyists aren't so lucky.
If you stay in the suburbs, which are heads-and-shoulders safer, you gotta factor in the public transit factor. As bad as the city is, there's nothing more discreet than taking train or bus, where you're basically hiding in plain sight. So if you stay in a suburban hotel, try to stake a claim near Pace bus transit centers. It's a lot easier to "hide" on a bus than to explain why your car is in an area you don't normally drive to.
River North is a shit show. Becoming more dangerous all the time. Better off on the Mag Mile. Schaumburg is a great place to stay. Lots of hotel choices and there's a huge indoor shopping mall and good restaurant choices. Very short Uber rides.
Shopping, Rivers Casino. plenty of good restaurants and outdoor concerts in the summer time. Oakbrook is about a half hour from O'hare, Rosemont is five minutes away...
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