Lincoln Park & Wrigleyville are fun areas. When I went back in February, we caught a Rockets game at a bar downtown and if I remember correctly, it was called McFaddens. They had League Pass. Anyways, good luck to you. Chicago is a lot of fun but it is much different than here. If you plan on being a city dweller most of the time, sell your car. Public transit there is very reliable/cheap.
Chicago Millennium park to see Chicago bean Hancock center, sears tower to see aerial view Navy pier to see world trade fair site Magnificent mile Michigan ave shopping and dining Wrigleys field Lincoln park area of chicago-bars, free public city zoo, Michigan lake beach access Eateries- purple pig tapas restaurant off Michigan ave, restaurants off Bush st. like the drawing room, mastro's steakhouse, Moto's restaurant (one of the best in its kind in the world), Al's beef - fast food Italian dipped beef sandwiches