Brian proposed to Kylie right outside the Adler planetarium in front of an unbeatable view of the best skyline in the world (we might be biased). There is also the Field Museum and the Shedd Aquarium in this area.
The Game Room is a bar located in the Chicago Athletic Association Hotel. It has a fun old-timey atmosphere with table games like bocce ball, fooseball, shuffleboard, chess, etc. There is also a great rooftop bar called Cindy's on the top floor of the hotel.