Chicago in September

For steak also consider Gibsons and Gibsons Italia, maybe Erie Cafe. Gene & Georgetti used to be really good but it's had a rough few years under new management. The italian menu there is better than the steak menu nowadays.

Take in a game at Wrigley if possible. It’s worth staying and extra night.

I’ve tried all 3 of those pizzas. Pequod’s is my favorite but a little out of the way- but Giordanos is solid too. Not a fan of the Malnatti’s butter crust.

Plenty of good steakhouses in Chicago- Google a few lists and pick one of consistent top 5 that appeals to you.

Willis Tower is cool you can step out into the glass box and look down below. We did Willis at night and Hancock building during the day.

Skip Navy Pier. Didn’t find it very interesting at all. You don’t have to go to the Bean per se but it’s in a nice park in the middle of all the museums so you may walk right by it.

Take the architecture boat ride. Even if you don’t care about architecture it’s a nice ride through the city, very relaxing.

Chicago has some world class museums. Take in a couple if you can. I’m not an education buff but I was impressed. One of them has a full length German submarine on display. Amazing.

If deep dish or pan is on your list, I'd go with Milly's in Uptown. Otherwise, most of us prefer bar / tavern style - best of that bunch that would be accessible for a weekend visitor is Professor Pizza, Michael's, Phil's, and Pat's.

For steak, run with Bavette's, Butcher and the Bear, Smoque Steak, Brasero, or Boefhaus.

I've lived in Chicago for over 10 years and have been to Navy Pier once, maybe twice. If you're planning to skip the Bean and Mag Mile, no real reason to do Navy Pier, either.

Would recommend using the train to your advantage. It's a very convenient way to see Chicago. Most of our residents live in the neighborhoods, and I always encourage folks on here to see "how we live," so-to-speak. The Loop and River North are fine for what they are, but hardly a representation of what Chicago is. To give you quick reference of good walking neighborhoods with an abundance of bars/breweries/restaurants: Logan Square, Pilsen, West Loop, Wicker, Lincoln Park, and Lincoln Square / North Center / Ravenswood. Of the bunch, Logan and West Loop are pretty easily the best restaurant neighborhoods, with Logan outpacing West Loop in quality cocktail bars.

Some guy on Reddit created a "walking tour" of sorts that would be super helpful for anyone visiting Chicago: LINK

ETA: Aside from this, I'd probably use Search on here and F&D board - plenty of Chicago threads to read through.

ETAx2: Don't go to Wisconsin and start calling it Wisky. Not sure how this ever became a thing.