Well you have come to the right person ! I hope :) I am the travel person for our ballpark chasing. I search for hours/days/weeks (dont tell my boss) For Chicago we stayed outside of Chicago in the suburbs BUT there are some good deals if you look on websites such as travelzoo for hotels in the city. I have a marriott cc that offered a deal so i searched their website and based my decision on the closest hotel to the city of Chicago which was 18 miles outside of the city. We would take the metro into town each day. Wasnt bad but we didnt run into a few hiccups. When we went to Milwaukee we drove there saw the game and drove right back the same night (crazy I know) it is not far maybe 2 hours or slightly more. We didnt see Milwaukee at all. Just the game and thats it :( but we sometimes do that when going to a game unless theres really something i want to see in that specific city. IF you are going to spend any goof off time doing anything i would spend it in Chicago. Its a beautiful city with alot to see and do. We went to downtown Chicago, had deep dish pizza, walked to the Chicago riverwalk, Navy Pier, lots to see n do around downtown. Wrigley is such a small park i think any seats are great :) I love to walk around during the game if possible to really get a true feeling of the park and the people. Everyone is always friendly. Let me know if you have any other questions ! I am sharing with you 3 pics from our visit. The outfield view from Miller Park was one of the most insane views i have ever seen. It was like true art. The weather was beautiful that night and i really felt like i was in one of the most beautiful places I have ever been and believe me we have seen some beautiful places in the world !