Well, it’s really 280 miles to my friend’s apartment in Chicago, but there is a rest stop on the Indiana turnpike that is just about 106 miles away.
I will be heading there tomorrow morning for my Labor Day weekend. I haven’t been a tourist in Chicago since early high school, though I have been back to the area a couple of times in more recent years for curling events. But I have not been downtown.
I know things will be different, but I have only vague memories of my time there anyway.
Through all my travels with my boyfriend, Jon, I have learned what it is like to travel with someone else and how many fewer sights I see as opposed to when I am alone.
I do not yet know how much time I will spend exploring Chicago alone or with Linsey — it will all be determined by her amount of homework. So I selected a much smaller list of sights to see that I am quite excited about.
When I arrive Saturday afternoon, I hope to check out the Uncle Fun and Paper Boy shops, both of which are “gag-gift” stores. We will likely have pizza at Lou Malnati’s and then see Big James, a trombonist, perform at Kingston Mines, a legendary blues club.
On Sunday, I want to take an ArchiCenter tour to learn about the rise of the skyscraper. I also want to see “the bean” in Millennium Park and check out Navy Pier. I’ve picked out the Billy Goat Tavern on Michigan Avenue for dinner, with its famous “cheezeborgers,” and it is also a classic newspaperman haunt. That evening I want to stop by Green Mill, a lounge that is the home of poetry slam.
On Monday, I am looking forward to the Lincoln Park Zoo and then perhaps the stop I am most excited about: the Chicago Brauhaus, which has Schnitzel and Stiegl beer and Gulaschsuppe.
From there, I will head home and Linsey will be off to class. On my way out of town there are a couple of ice cream establishments I am considering stopping at and I have another must — the Robie House on the University of Chicago campus.
I saw the Frank Lloyd Wright house, along with his house and many others in Oak Park, on my original visit. I want to return to the Robie House because the restoration of the house is now complete (it was turned into a dormitory!) and there should be a fantastic gift shop. I wanted to be an architect because of Frank Lloyd Wright, so stopping to see the house is a must.
Is this list of activities manageable? I sure hope so!
travelin' the globe 
I’m driving to Chicago next week as well — I’m so overwhelmed because I want to do, see and eat everything! Thanks for the suggestions.
There is a lot I want to eat there, too! Perhaps you could pick a neighborhood or part of the city you really want to see and find thing there to do. I think it is always easier to plan when you have some parameters. Enjoy your trip!
Wow! what’s the must try food to eat there?
Hot dogs and deep-dish pizza are the foods Chicago is known for, so I would start with those!
It sounds like a busy itinerary but totally doable, especially since you have food on your list…that means you’ll have energy refueling stations along the way and you’ll be fine :) Chicago is a great place to be a tourist, enjoy!