How to: Chicago

My sister-in-law and her boyfriend have lived in Chicago for nearly four years. In that time, my wife has visited them a couple of times, my three year-old son has made the trip, and they have made countless trips home for holidays and other special visits. Meanwhile, I have somehow never mustered the gumption to go to the Windy City. Finally, over Labor Day weekend, I was able to make the trip, my wife and son in tow. I won’t pretend that this piece offers any sort of comprehensive look at the city, but I think the principles behind our trip will well serve anyone making a first-time journey to Chicago or any other big city.

1. Have a friend on the ground:

The value of knowing someone who lives in the city you plan to visit is inestimable. Everything I’m going to say after this point hinges on having had a very experience guide with us almost all the time. I’ve tackled public transportation in Atlanta, London, New York, and Boston, so I think we could have managed the trains and buses, even without my sister-in-law leading the charge, but there is absolutely no question that she made travel so much simpler than it could have ever been otherwise. We’ve all seen (and many of us have been) those people standing off to the side, consulting maps, their phones, or even hand-scribbled notes about which direction to walk, which stop is theirs, and which sites lie in which direction. The stress and time that this adds to any trip is immense, and if what you remember most about your time in a new city is the difficulty and frustration of simply getting from one place to the next, you’re probably going to wish you’d never gone. The alternative to knowing someone in the city is doing a TON of research up-front, but even if you put in the time, making a single mistake can upend all your carefully laid plans.

2. Don’t try to swallow the whole proverbial deep dish pizza at once:

One of the truths I’ve discovered about visiting a big city is that you have to accept up front that you’ll never be able to see everything worth seeing over the course of a single visit (especially a weekend visit); it just isn’t feasible, and thinking that it is feasible is a good way to ruin your trip. You’ll end up lamenting everything you missed rather than taking your time to really enjoy a select few things. Set modest goals; if you have time left over, then you can knock out a couple of bonus attractions and feel all the better for it. As an example, here was the rough itinerary for our two full days in the city:

Day One:

  • Take the train to Millennium Park
  • Explore the park, including Cloud Gate (the giant bean-shaped mirror sculpture)
  • Walk down Michigan Ave. to the Chicago Water Tower
  • Visit the LEGO store (Benjamin has a picture of his uncle next to a LEGO version of Woody from Toy Story, and he was desperate to see the thing himself), which features LEGO sculptures of the a giant dragon, a ninja,the Hancock Tower, Sears Tower, Chicago Water Tower, Marina City, and Water Tower Place.
  • Lunch at a Chicago-ey place. (We ended up at Giordano’s, but didn’t get a deep dish – I want pizza, not a pepperoni and cheese casserole. The “thin crust” pizza we ordered was delicious, in any case.)
  • Take a bus down Lake Shore Drive, past Soldier Field and along Lake Michigan, to the Museum of Science and Industry.
  • Take a train home.

Day Two (my sister-in-law was working, so we were at least partially on our own):

  • Get up at six, get ready, go to a soccer pub to watch Liverpool and Arsenal at 7:30 AM local time.
  • Go shopping at a few stores we don’t have near Lexington (we drove; it’s surprisingly easy – albeit time-consuming – to drive around Chicago if you have GPS, since the city is so spread out).
  • Go to Wrigley Field and cross off another legendary stadium from my “to-visit” list. Drew, my sister-in-law’s boyfriend, graciously agreed to drop us off about a quarter-mile from Wrigley even though there is a train stop right next to the stadium.
  • Take in a Cubs game.
  • Go home and play games during the evening as a relaxing end to the trip.

See? Relatively few “big” items on the list, but we enjoyed them all, took our time doing so, and after the fact, I don’t feel shortchanged in the slightest.

3. Make a mental checklist for future visits:

The great thing about step #2 is that it promotes future visits to cool places. As you go through a big city, make a mental checklist of all the things you want to do the next time you’re in town. For instance, I know that I want to hit the Field Museum next time and I think my son would love it. I might make time to go to the top of the Sears Tower or go to a blues club. I didn’t make it to a single book or record store (something I always try to carve out time for in major cities). But, now that I’ve been once, I know what caught my eye and I can make sure that I cross a few more destinations off my list next time.

4. Arrive and leave under cover of darkness, if at all possible:

Living in a small town like I do, or a smallish city like I did in college, has in no way prepared me for the true horror of rush-hour gridlock. Coming into the city on Friday via the Dan Ryan expressway (I don’t know who Dan Ryan is, but I assume that he must be a particularly nasty serial killer to warrant naming that twisted hell of a road after him) during Labor Day weekend traffic was maybe the worst experience I’ve ever had in a car, and that includes the time I fell asleep at the wheel, ran off the road, and woke up in mid-air, only sky visible through my windshield.

I challenge even the most patient, easy-going people I know to spend seven hours in a car, nearly two of which are spent stuck in creeping traffic just a mere few miles from their ultimate destination and not have serious doubts about their sanity. My anxiety levels were through the roof during the seemingly endless final portion of our drive, and I spent most of the rest of the evening still in a boiling rage, irritable about everything even long after I should have just gotten over it and been glad to have survived the road.

We left the city at about 5:45 AM on Monday, and we didn’t have to sit in traffic for a single minute. If I had it to do over again, I would under no circumstances try to get into the city before 10:00 PM. My nerves just can’t handle it.


Chicago is a great city, and September is a really good time to visit. I can’t say I’d want to be there from late October through March, but if the weather’s tolerable, it’s absolutely worth your time. I don’t really have the space to tell all the stories worth telling from our time there, but I do have one piece of parting advice: If you see a Cubs fan in the wild, do not approach it. Keep your eyes down and just keep walking.

Tags: , , , , ,

Categories: Skin A Cat

Follow TTAF

Subscribe to our RSS feed and social profiles to receive updates.

No comments yet.

We want to hear from you, leave your thoughts below.

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s

%d bloggers like this: