There are several wineries, breweries, and restaurants along the Chicago River that are perfect for sightseeing and people watching!
We love doing the tour, we've done it 6+ times! Its a boat tour that goes down the Chicago River and a perfect way to learn about the city. There are plenty of tours to choose from so just google "Chicago River architecture tour" and pick one that works for you.
Yes, Chicago has beaches! North Ave Beach, Oak Street Beach, or Ohio Street Beach are some I recommend. You can also walk, run, and bike along the lakefront trail.
Bride's recommendation for Deep Dish Pizza