Just got back from a 5 day trip here with the wife & kids (9 & 10). Loved it! We stayed at the Residence Inn at 201 East Walton... pretty nice location & were able to get a suite with kitchenette for about $200/night. Came with a free breakfast that we gorged on. Cooked our own meals a couple of nights just to save some cash & relax. We probably walked an average of 6 miles a day while we were there.
***GET THE GO CHICAGO PASS*** Saves you money & allows you to skip quite a few long lines. This pass is good for Shedd, Field Museum, Art Institute, and one of the Sears Tower/John Hancock. There were a couple of other places it was good for, but I think you can only do 4 out of 6-7 options. Very helpful.
Pros:
The Lincoln Park Zoo was free & excellent. The surrounding park was lovely.
I was impressed with the beaches along Lake Michigan. If I was a younger man, I'd have been right in the middle of it. Boats tied up partying off shore. Packed beach. (No pirate flags, jacked up 4x4's.. much less WT than Port Aransas.) Runners and bikers everywhere. Beach Volleyball, bikinis, music, alchohol.... sigh. To be young. (er)
Field Museum was ENORMOUS & an all day affair. Great museum.
Shedd Aquarium was ok, not much compared to Monterey Bay. Spent about 3-4 hours here.
Art Institute of Chicago has some great paintings: "Nighthawks" "American Gothic" were a couple of my favorites. Lots on Monet, Van Gogh & Picasso. The medieval armor was nice for my wife & I (GoT fans)
We decided to do the John Hancock Tower instead of the Sears (Willis) as it was closer to our hotel & had views of Lake Michigan Shoreline. The "TILT" gimmick was $7.00 & my 9 year old and I both liked it.
Millennium Park was a cool hangout.. saw a free symphony & enjoyed wandering around.
Saw the "Picasso" from The Blues Brothers. (We were on a mission from God) The kids liked climbing on it.
Took the river Architecture tour. Boring for the kids, but the wife & I drank beer and tuned them out. Very interesting if you are into this sort of thing.
We took Lyft everywhere... all the drivers were very nice.
Giordano's Pizza was very tasty.
Cons:
The newly opened Chicago "Riverwalk" is ok, but the restaurants are terrible. We ate at a place called "O'Brien's" or something like that. They forgot my order. And we found a piece of glass the size of a half dollar in the Hummus. Luckily we found it before it made it into anyone's mouth. Meal was comp'd... but it was all I could do not to lose my s&*t on the idiot waiter who said he wouldn't make us pay for the Hummus.
BLM rally. We came up the stairs from the riverwalk in front of Trump Tower & unavoidably had to walk right next to it. Kids were freaking out at all the screaming & police.
Anyway... had a great time & 5 days is just about the right amount of time to spend there. Another day & $1,000.00 and we could have seen the Cubs play. Oh well.