This summer we went to Chicago for the first time ever. I can't believe how much I loved it, and that I don't usually hear people talking about it in a "you have to go there" sort of way. Where else would you be able to walk ten minutes from your hotel, down to the lake, swim, play in the sand, meet some kids, and then walk back to the hotel, through downtown, with your swimsuit on and a towel around you.
We loved our meal at Longman and Eagle (loud enough to go with a kid, but certainly not a place for picky eaters that need to be accommodated. We also checked out the inn they have upstairs, and it's a great neighborhood-vibe inn if you were on your own in Chicago. Definitely not a family destination--unless your kids are older, and could sleep in a separate bedroom (no adjoining rooms).
We loved our meal at Publican. Another very loud place, and a place that has a bigger menu so more possibilities for kids who may not want what you're eating. Get a booth where they shut you in like you're in a stable.
We were lucky enough to stay at the Elysian, which is a new-ish hotel, and is fantastic. Loved the staff (who don't accept tips), the indoor pool, and the hotel restaurant Balsan. In that neighborhood, we liked to get coffee and pastries at this Belgian cafe, Hendrixx.
We didn't get to fully check it out, as this airport playground was on our way to baggage claim, but it looked great from the outside.
And although everyone said to try a hot dog from Portillo's, we didn't love it. The more discerning locals said Hot Doug's was a must, but they had weird hours. I know it sounds crazy, but our best hot dog was in the airport.
One night, we were exhausted and wanted to eat somewhere we could walk to, so we went to the Rosebud Steakhouse. It was a great old-school restaurant, where you walk out with a bag of leftovers, because each portion could feed a whole famly. We ate the mac and cheese for 2 days. On our walk back to the hotel, we checked out the Drake Hotel.