As a Chicago resident (who is hoping to join your team in Dallas soon!) I have to say, the Architectural Boat Tour along the River is an absolute must! It's the best "sightseeing" part of Chicago and you get a complete history of the buildings and the city. I think it ends in October sometime (only runs summer time) so be sure to check it out. It runs from Navy Pier.
If you want a nice summer glass of wine on a grassy roof terrace check out the bar at the Park Hyatt. It's called Nomi. The restaurant itself is a bit pompeous but the roofterrace bar is incredible a la fresco. Enjoy!
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