Chicago, IL

I’ve done my fair share of traveling. So when it came time for my wife and me to make the drive to Chicago for our week long adventure, I figured my single backpack of clothes and dreams would suffice for survival. My wife knew better. While my off the cuff bachelor adventures suited me well during my single years, taking a family on this trip was going to be a different beast entirely, even if it was just the two of us. So, a week before, while I savored for the chance to see a city unknown to me believing that gut instinct would be enough, Rachel had printed off and filled out an entire checklist of things to be done before launch.  It was an Oscar and Felix moment. So after some brief discussion on the theory of vacationing that I’ve since stored in my memory along with a mental memorabilia box labeled retrospect here is what Rachel and I learned together on the Road to Chicago.

Know where to go and where not to

While seeing the tourist destinations of Chicago: Lincoln Park Zoo, the Shedd Aquarium, and the Skydeck up top Willis Tower (the people of Chicago will be sure to remind you it’s still the Sears Tower while your there) are all that some will do, others like me want to see the heart and soul of the city. This usually requires a venture off the beaten path. In any city or tourist destination there are just some places you do not go whether it’s the destination or a shortcut so do your research. Sometimes the signs are easy to spot: cars shells on cider blocks while the occasional 2016 Escalade circles the block, but other places aren’t so obvious until the sun sets. Learn about the local area beforehand. There are usually articles online about the good and bad neighborhoods of any city or just ask people. Good research means good finds.

It takes time to do EVERYTHING

So remember my quip about the Skydeck up top Sears Tower? Yeah, we didn’t do that. You would be surprised how much time everything took. Be realistic about time constraints. You aren’t getting through Shedd Aquarium in an hour. Our hotel in Waukegan while inexpensive was a good hour away from downtown Chicago. And it runs on a tight schedule. So to be back to the train to Waukegan by 9 pm was already a constraint followed by the time it took to reach each destination then experience it. Don’t forget food. So by 9 pm, with our last chance to do so left somewhere at a hotdog dive, we said goodbye to the Sears Tower and the missed gorgeous view it offered. Give yourself ample time or you’re going to miss something because you spent three hours looking at dolphins, awesome dolphins.

Walk with a hint of Subway

Don’t drive. Not in the city, it’s just not worth it nor is it fun. Get out and be with the city instead of looking at it from the window of a car. Take public transport then walk.  Now you might be saying “Nate, if you had driven you would have been able to see the Skydeck” but you would be wrong. For starters if you followed step 1 you will find yourself in some really gorgeous neighborhoods. The streets are lovely full of great architecture, lined with little hole on the wall shops and hidden gem cafes. Second it’s cheaper than the gas you would have spent to get here, quicker than the time it would have taken to actually find a parking spot, and both quicker and cheaper than retrieving your car from the impound because that wasn’t really a parking spot you stashed your car hours earlier.

The locals know their city better than you do

Hungry? Yeah there is a McDonalds on the corner but remember you came here to experience something new not live for a week like you do in North Dakota! Chicagoans love their cuisine and are willing to share their favorites if you just ask. With just a little inquiry Rachel and I were guided to a little pizza joint with some seriously deep dish pizza. It was fantastic (I still prefer New York style but don’t tell them I said that).  Ever have Blue Moon ice cream? I still crave it as I write this. Yelp or Zagat online are also great resources to discovering a new dining favorite, often they are rated by locals. More importantly, by asking, you can learn what is and is not worth your time. You see, Waukegan, where we stayed, is best known for their Six Flags Amusement Park. It was always part of the plan to spend some time there but it also meant sacrificing some downtown Chicago time. Even though Six Flags was a marquee event on our Chicago vacation, I still had doubts. So I asked around. In little time, I was told how overrated Six Flags was and how great some of the other plans we had as backup were.  It was decided and we never looked back. Maybe Six Flags would have been fun, but nothing beat the experience we had instead.

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