If that hotel rate is cancellable, you could book it now, and look again closer to your dates.

Our family has always loved the Museum of Science & Industry.

The Architectural Boat tour is excellent.

You may want to consider a suite hotel (or an apartment thru aiebnb or vrbo) so you can easily & cheaply have breakfast in, you can keep you child's favorite snacks, and the adults have someplace to hang out after the little one goes to sleep. At that age, by children & grandchildren were in bed by 7:30.

Of all the suggestions here, the best for your 1 year old are Lincoln Park Zoo and the Shedd Aquarium. I have taken toddlers all over the city and they also enjoyed long walks in their strollers, so much to see. Take him over to Oak Street beach too.

Citylights, not to beat a dead horse here, but you can have a lunch/brunch for almost the same price as a drink in the lounge and probably better for a family. Check out the drink prices. http://www.signatureroom.com/TheSign...alty-Cocktails

You may save money by joining a museum local to you and taking advantage of the reciprocal membership agreements. We are able to get free admission to the Field Museum. Museum of Science and Industry and the Alder Planetarium through our local museum.