I live in Chicago and the top things my kids liked as toddlers included:

Chicago Children's Museum
Peggy Notebaert Nature Museum
Lincoln Park Zoo

You can find more things to do here: https://thetravelsisters.com/things-to-do-in-chicago-with-toddlers/

Dorothy Nootebart (sp?) bature museum is fabulous and has lots of hands on exhibits. I’m sad my kids aged out of it. Also the Lincoln Park zoo is great.

My 2 yo son LOVED the Children's museum and the bean. There was also an awesome playground really close to the bean where we spent a bunch of time.

The boat tour was terrible for our toddler, because it was too unstable for her to walk around, and being still for the duration of the tour was no fun either.

The Chicago History Museum (www.chicagohistory.org) is great -- we go every time we're in Chicago, and my daughter loves it.

Also, as others mentioned, the children's museum at Navy Pier.

Do you think he'd be scared to go up to the top of the Hancock? it's really cool.

There's a nice Children's Museum at Navy Pier.

If you would like to go to the Field Museum or the Shedd, both are very friendly to small kids. He's a bit small to get much out of it, but no one would be bothered by him being there.

Architectural boat tour will be a little dry for most toddlers -- slow boat, lots of talking and adults wont' take kindly to a lot of moving around.

Take him on the water taxi instead.

The millennium part fountains and 'bean' is a lot of fun.

I live in Lakeview.

Your toddler will LOVE Maggy Daley park -- it's fantastic -- the best playground I've ever seen! My toddler expecially loves the "enchanted forest" and the part with all the slides. It's just next to Millennium Park, very near Gold Coast. At Millennium Park, my toddler likes "the Bean" (Cloud Gate statute) and LOVES playing in Crown Fountain (although I don't know when they turn on the water or if it will be warm enough next weekend anyways).

My toddler's favorite museums are the Shedd Aquarium and the Children's Museum at Navy Pier.

Yolk is very good. If you will be in Lakeview for breakfast, some good spots are Bakin N Eggs, Wishbone, Kitsch'n on Roscoe, and Crosby's Kitchen. A great park in Lakeview is Margaret Donahue park (it has a wonderful water park within it, but again, might be too early for that).

My favorite beach to take our toddler is Montrose Beach (near Lakeview, not downtown).

We are going to Chicago for the holiday weekend and staying at the Waldorf Astoria so will be in the Gold Coast. We will also be in the Lakeview area visiting family. Besides the zoo, beach by our family's house and hotel pool, what are some fun activities for toddlers? I think my son would love the architectural boat tour. What museums are great for toddlers? Any Gold Coast parks or playground to recommend? Friends recommended Yolk for breakfast and American Pancake House. We need recs for breakfast, lunch and dinner. My son likes breakfast, Mexican and Asian foods best.