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Originally Posted by mahtofire14
We're staying in Oak Park which I've heard is nice and right by the Wright museum which I'm excited for. I also though about a Blackhawks game but figured I wouldn't be able to get tickets anyway. Also I really wish I could hit a nice B&M with a couple of you guys but I don't think I could talk the lady into that unfortunately
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There is a ton of stuff to do in your area. Just in Oak Park alone, they have a Frank Lloyd Wright house and studio tour throughout the day and tours of the Unity Temple, both of which are national landmarks and defining of the Prarie Style of architecture. If you get on a Wright kick, go tour the Rookery downtown on LaSalle or the Robie House near UoC. If you hit the Rookery, visit Jack Schawrz Importers at 141 W. Jackson on the 1st floor.
Take her to the former Sears Tower (now the Willis Tower), hit the 101st floor and go out on the glasswalks for a picture that will last a lifetime. Just dont look down!
Take the train to the Chicago Loop and spend the day on Michigan Avenue. Visit Heaven on Seven for lunch (one of my faves) or Bandera on Michigan.
You really cant miss in Chicago - tell us more of your interests and we will get you there.
As for train safety, Scott II rule #1 for taking the CTA anywhere is to make sure you get on the RIGHT train! Study the maps! If you end up late drinking downtown, take a cab - it will run $20-$40 to Oak Park, but they are safe and ubiquitous.