No. of Recommendations: 1
Fear that I'm too late here (though I hope not) but wanted to share a few thoughts.

First, thought Michigan Ave. and the surrounding areas are littered with great steakhouses, I'd encourage you to branch out a bit. Chicago offers so many great restaurants--and many great steakhouses (Chicago Cut, Gibson's Mortons, Mastro's, RPM et al). But I'd strongly encourage you to try something more authentically Chicago. Basically, it's my opinion that you can get a great steak in many cities. Try something you can't get elsewhere.

The Gage is ~200 S. Michigan, really outstanding restaurant with a great beer and scotch menu. Will need reservations for dinner, but a good happy hour spot as well. We've always enjoyed it: https://www.thegagechicago.com

I know Rick Bayless is a bit polarizing, but I really like Topolobampo (http://www.rickbayless.com/restaurants/topolobampo/). Excellent Mexican restaurant that you can't recreate in other cities. Would encourage you to explore options like this.

If you find time for a game/concert/show, this guide is helpful: https://www.vividseats.com/chicago-venues-guide.html Uber is the name of the game, but CTA is pretty robust, and you could potentially save a good bit of money over the weekend just by getting a Ventra card and leaving a few minutes early.

It doesn't seem like your schedule will allow, but there are a number of free concerts in Grant Park. You can pack a blanket, buy a bottle of wine, and sit out on the lawn, as the sun sets, while you're enjoying nice music (https://www.grantparkmusicfestival.com/the-music/2018season) Can get busy on Saturdays.

Also, both ORD and MDW can be a zoo on Sunday afternoon. If you can extend your trip, take Monday off, and travel back Monday afternoon, you can have a whole extra day and potentially a much nicer trip home.

Enjoy your trip!
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