One of those cities where it’s impossible to see even a fraction of it over several trips, so there is no such thing as an exhaustive list.   Here are five places that I found to be quintessential Chicago.

Wrigley Field – I’m only a passive baseball fan, but this is one of those Bucket List kind of places.   So much history.    Having a video version of Harry Carey lead the 7th inning stretch was priceless.   If only I’d made a trip for the real thing back in the day.

The Art Institute of Chicago – whatever your taste, chances are they have it here.   Probably a lot of it.

Millennium Park/Cloud Gate – anything nicknamed “The Bean” can’t be all bad.

Le Colonial – it wasn’t on my scouting report, but was highly recommended by a friend and right around the corner from my hotel.  I went to a couple of landmark restaurants while I was in Chicago, but this was hands down the best meal of the trip.  (Honorable mention to a Wrigley beer and hotdog).

Signature Lounge (or any place with a skyline view) – I’ll admit this place is super touristy, which is not normally my thing.  Sometimes you have to suck it up to enjoy the amazing panoramic views of this beautiful city.  Even better if you can make it for sunset.

Bonus Round – Five More Restaurants and Bars

Osteria La Madia – I ended up here after music at Blue Chicago only because it was open later than most places on the block.  It ended up being exceedingly good Italian food and a super friendly staff.

Hugo’s Frog Bar and Fish House – I was trying to get into Gibson’s but it was always too crowded.  It’s next door neighbor, Hugo’s Frog Bar, ended up being a great alternative.  They apparently share a kitchen and it was a more subdued setting to enjoy a drink and a nice meal.  Plus, the bartender recommended Celtic Crossing for a pint of Guinness, which ended up being another neat find.

Blue Chicago – I was turned off by the time the music started due to the ill-mannered tourist crowd.   The staff, who seemed weary from the fray, was surly at best.  My mood changed when the music started.  And turns out the staff are nice folks once you get to know them and they realize you are not another tool.

Andy’s Jazz Club – the crowd here was a better mix of local versus tourist than Blue Chicago.   A lot of people intent on listening to – and appreciating – good music.

Bernard’s Bar – I had a bit of a love/hate relationship with my visit.  The service was not nearly as sharp as I’d expect for a bar in the Waldorf Astoria and the prices that go along with it.  But this is one of those hotels where legit Chicago business deals get done over a couple of martinis.  I literally witnessed a multi-million dollar commercial real estate deal get done on a handshake at the table next to me.