If you visit Chicago, you could go to the ultra famous Willis/Sears Tower or John Hancock Building observation decks (both offering an out-of-building experience with glass balcony or tilt out). You could wait in long queues, pay an entrance fee, and deal with crowds for that fleeting experience.
OR, you can do what I did 😉
The lounge/bar at John Hancock is right above the Signature Room on the 95th floor, and boasts incredible views over Magnificent Mile and the shore of Lake Michigan. Miles and miles of flat Lego land, kilometres and kilometres of water. I’ve never seen anything like the lake, it looks like a completely placid ocean. Apparently the whole Korean peninsula can fit in it! The panoramic views, taking your sweet time over a (generously alcoholic) cocktail, enjoying relative quiet and great service – can’t get any better!
But it did. A fellow visitor who happened to sit next to me made conversation and we had a full hour of entertaining banter and conversation and another drink or two. I love these special, serendipitous moments while traveling! If you know enough about Chi-town’s architecture it’ll be a treat to spot and observe icons on Magnificent Mile from that height, or if you’re blessed enough you’ll be seated next to a structural engineer who can point them out for you (I was excited to spot the retro Maccas/Mickey D’s lol, find in the pics above)!
I went there on a late afternoon on a weekday and didn’t have to wait to go up or get seated. I imagine nights are busy, especially on weekends, so head in before sunset and watch the city lights come alive. You could then head into the Signature Room for dinner or, even better, get out for some Lou Malnati’s deep dish pizzaaaaa (*actually drooling)! From memory, the cost of the cocktail (Aussies – don’t forget tax and tip charges) basically equates to the entrance fee of the observation decks. For me the cost more than paid for the peace and lovely experience I had!
* Bonus pro tip: get pics from the Ladies’ restroom (if you are a lady)!
Visit the Signature Room Lounge: