My Favorite Secret Chicago Spots

Chicago has long been a city of excitement and mystery.  Although I spent my first 17 years in Iowa, I consider Chicago to be my adopted home.  I've always preached the awesomeness of Chicago festivals (many of which are free), Movies In The Park, the Lincoln Park Zoo, etc etc etc.  There are just so many incredible places and things to do.

Besides the Art Institute, the Chicago Theater sign and the Marshall Field's clocks, I took a visiting friend on a private tour of my favorite secret and sometimes hidden Chicago gems.  This is my Chicago.

  • Lou Mitchell’s – An iconic greasy spoon diner, Lou Mitchell's has long been known as the first stop along the legendary Route 66.  The servings are huge, the staff is friendly and the service is LIGHTENING fast.  We had been sitting for about 15 minutes before our waiter was back with our piping hot orders...and he apologized for the wait!  Even as we waited (maybe) 5 minutes in line for a table, the hostess was handing out cinnamon sugar donut holes to keep us satisfied while we stood.  On each table sits a jug of maple syrup, jars of grape jelly and orange marmalade, carafe of creamer and a sifter of cinnamon.  I had an omelet which had to have been made from 8 eggs, breakfast potatoes and toast.  My friend’s order of ham and eggs threatened to break the table under it’s heaving mass of FIVE poached eggs, two enormous slices of ham and a healthy serving of breakfast potatoes.  My omelet wasn’t “done” enough for my taste, but I happily picked out the cheese and broccoli.
  • Union Station – Chicago’s Union Station has been the background for several movies, including a dramatic scene in The Untouchables.  I took my friend there, however, to check out the station’s Grand Hall, designed by Daniel Burnham.  You may remember Daniel Burnham as Chicago's man with a (city) plan.  The Beaux Arts style room has a fantastic glass ceiling and is flanked by Corinthian columns.  Enter from the south entrance, so that you can have a private perch above the crowd.
  • Chicago Cultural Center – If you don’t already use the incredible resource that is the Chicago Cultural Center, you really should.  I was super bummed to find out I’ve been missing a lecture series called “Morbid Curiousity,” which looked into topics like mortuary art and medical oddities.  Super weird, but super interesting.  I walked my friend through a few art exhibits before eventually landing under the gorgeous Tiffany stained glass dome.  If you have a free day, you should definitely check out one of the free Chicago Greeter tours.  These include topics of interest and neighborhood specific tours given by resident Chicagoans.
  • Sculpture Garden at Terzo Piano – Terzo Piano is the restaurant attached to the new(ish) Modern Wing at the Art Institute.  A bridge seamlessly extends a welcoming arm from the museum to Millennium Park which connects it both physically and symbolically to the city.  On Terzo Piano’s patio is a gorgeous view of the city and free sculpture garden with rotating exhibits.
  • Blackstone Hotel – This is my favorite hotel in Chicago.  Incredibly historic and closely tied to a bygone era, the building and its interior have that heavy, dark wooded look that is so very Chicago.  I took my friend on a private tour, peeking into a conference room that was once Al Capone’s barber shop and one with an interior shipped and reassembled from a British Lord’s home.  I took him through the Art Floor with its dramatic red rugs and walked through the beautiful white ballroom, before finally leading him to the lobby and its giant fireplace.  Make sure to check out the tiled elevator floor!  The Blackstone is also home to the original Smoke-Filled Room.  If no one is currently staying in the room, the staff may let you check it out.
  • Palmer House Hotel – The Palmer House Hotel’s lobby reminds me of the Great Gatsby.  I don’t know much about the history of the hotel, but the ceiling in this place is unmatched.  Using escalator access makes it seem as if the room is being slowly revealed to you.  We stopped at the bar for a coffee and just took it all in.  During the winter, I like to have a hot chocolate at the Palmer House after ice skating in Millennium Park.
  • Terrace at the Conrad – I have always loved coming to the Terrace at the Conrad.  Located on the 5th floor, you feel as if you are being swallowed up by the buildings around you.  Cocktails are super yum, the staff is friendly and on summer Sundays a movie is played in the open air.  Have a bottle of champagne chilling for when your +1 arrives.  Just do it.
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  • My favorite secret spot is a lot more humble. The downstairs of the Arby's at 20 East Jackson is relatively large and always empty. It's always fun to have THAT much room in the loop all to yourself.

  • The Blackstone Hotel is one of our hidden gems. There's a lot of history there. I've been in the smoke filled room - they've preserved it nicely. What a great experience to be where so much history took place!

  • In reply to salisbury56:

    I absolutely love the Blackstone Hotel and was also super privileged to see the Smoke-Filled Room. So incredible. I always recommend a visit.

  • Thank you for sharing these hidden gems! I miss Chicago and it's beautiful architecture. When I worked at a bank in the CBOT I use to enjoy walking through the Options Exchange on my way to the train during the Holidays - the Christmas tree made out of poinsettia plants was lovely - it was something I looked forward to seeing every year. On a darker note - as far as entertainment goes - nothing beats The Exit - great place to people watch!

  • In reply to ArielPlath:

    I've never been to Exit, but it's been on my list for years! I love something with a little grit.

    Also, maybe it's just because fall is on it's way, but the poinsettia Christmas tree sounds lovely. :)

    Thanks for the comment!

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