We try to book a hotel in the River North area of downtown. You can walk to a lot of things.
Activities:
Art Institute (It was cheaper for us to be annual members for $115, 2 adults and all children under 18 get in free than to buy the tickets at base price, $142)
Museum Campus (Field Museum & Shedd Aquarium)
Museum of Science & Industry (The U-Boat exhibit was extra but worth it. Wife's grandpa was on a sub in WWII)
Navy Pier
White Sox Cubs Game (The only reason to see the Sox is if your favorite team is in town to beat up on them)
If you have a Zoo or Science Center pass in your area, check for reciprocity or discount tickets. When the kids were growing up we had the DSM Science Center/Blank Park Zoo pass that saved us lots of money at the Chicago Museums.
Activities:
Art Institute (It was cheaper for us to be annual members for $115, 2 adults and all children under 18 get in free than to buy the tickets at base price, $142)
Museum Campus (Field Museum & Shedd Aquarium)
Museum of Science & Industry (The U-Boat exhibit was extra but worth it. Wife's grandpa was on a sub in WWII)
Navy Pier
If you have a Zoo or Science Center pass in your area, check for reciprocity or discount tickets. When the kids were growing up we had the DSM Science Center/Blank Park Zoo pass that saved us lots of money at the Chicago Museums.