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Challenging Myself with Travel, Part 2: Going Solo

I recently took my most solo trip. Now, this doesn’t include the months I’d lived in Spain. However, I have some really close friends who live in New York and suddenly I’d gotten the overwhelming urge to see them. It was January, so since not many people want to be caught in NY during that time of year, tickets were cheap. And that didn’t even matter so much because I had points and miles that I was able to use in order to get myself a free flight.

But, who would I go with? I wouldn’t want to fly across the country all by myself would I? I asked a couple close friends if they wanted to join me, but they weren’t able to. I started to think that I’d just have to call it a day and plan on heading out there another time.

Wait, I told myself, I don’t need to have someone there with me. I have friends there, I really wanna go, why not?!

So I booked a ticket. But this booking didn’t just take me to New York. I’d always had adesire to see Chicago? Why? It’s hard to answer. I’d always just had a desire to see it! I mean, you can’t go wrong with classic deep dish pizza right? So I built that into the itinerary as well. I didn’t even know anybody in Chicago. But I knew it would all work out.

Stoop kids afraid to leave their stoop

This ended up being one of the most memorable trips I’ve ever taken. Catching up with close friends in New York that I hadn’t seen in such a long time really made for a great time. I can’t recall the last time I’d laughed so much over a short period of time. You know those friends where when you’re with them everything is funny? Well that was my experience, and it was a blast.

Getting to Chicago was quite an adventure too, as I felt even more alone upon my arrival. I didn’t know anyone there. However, a friend of a friend offered to show me around for my two days there. And a friend of a friend of said friend was willing to let me stay at his place. So I felt pretty well set up. Making new friends there in Chicago came pretty easy. Meeting up with other friendly people made the transition even easier.

What great hosts they were! Probably my most memorable experience in Chicago came in the form of a burger. Yes, a burger. We went to eat at a spot called Au Cheval. But get this… It was a Monday night. There was a solid snowfall that left the roads hard to traverse. You’d think these elements would contribute to a slow level of business at a restaurant.

Well apparently to an extent, it did. My new friends marveled at the fact that the wait would “only” be two hours tonight.

Two hours?! I thought, keeping it cool in my demeanor. Well, this place had to be worth it.

Two hours later, once we’d had a drink (and I’d had a Chicago Dog!) next door, we sat down and experienced what I’d call culinary ecstasy. The burger I ate was on another level. Seriously incredible. Perfectly cooked, dripping with melted cheese, stacked high with the thickest bacon, complimented with a delicious egg, sandwiched between perfectly buttered bun slices, and joined with perfectly salty fries. It was every burger lover’s dream come true.

And of COURSE, I had to indulge in deep dish pizza. It’s basically the reverse of what I’m used to, with the meat toppings on the bottom, cheese above that, and the sauce on the very top. Two slices and I had to tap out.

Just getting around the city was really cool. I say that figuratively and literally, as the temperatures dropped well below freezing, even by Chicagoan standards. While my fingers at times felt like they were going to give up on me and separate themselves from my hands, I hung in there. From rooftop drinks with friends, to movie nights with the heater blasting, it was really great venturing out on my own like that and traveling.

So if you’re ever in Chicago, be sure to

  1. Go to Eataly, an Italian marketplace with food shopping and dining. The squid ink seafood pasta (complete with BLACK noodles) was fantastic!
  2. Check out the Art Institute of Chicago. I’m not always into museums, to be honest, but this one was really interesting! There were plenty of pieces that I’d seen before but had no idea were there in Chicago. Traveling tip: the last hour of the day is discounted, too.
  3. Of course, without a doubt, no matter what the wait, no matter what the weather… GET A BURGER AT AU CHEVAL. You’ll thank me later.
Brand new friends in the awesome Chicago

As much as I enjoy being around people, getting an opportunity out there on my own helped me to challenge myself, to put myself out there and really see things on my own initiative. I’d hop on the opportunity again in a heartbeat!

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