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1) Definitely a boat architecture tour, there are so many companies and tickets are pretty affordable so doing it on a nice sunny day would be awesome
2) Brunch at Cindy’s rooftop
3) Walk around the lakefront (especially close to Lincoln park / Lakeview area), as it’s less crowded. Can pack food and drinks for a nice picnic and spend a whole day or couple hours, up to you.
4) Lincoln Park Zoo (if the family has kids)
5) Visit Shedd Aquarium
Did Cindy’s rooftop last summer with my parents was was greatly disappointed - maybe because views from my home are better and the food is expensive and overall subpar
Ask them to bring you potential significant others ?
Look into an outdoor concert I know they have them in millennium park in the summer. Cubs games are also a great idea! I think it’s also fun to show your family your favorite spots by your house so they can get to know what you like to do! Also if your family has any specific interests or traditions you could find something related to that for you all to do.