Illinois Solo Travel USA Mid-West Travels

I Backpackish Chicago

Backpacking Chicago
The Bean in Millenium Park

You’re probably wondering what the hell do I mean by backpackish Chicago, right? Don’t worry when I told my friends I was going to backpackish Chicago even they gave me a funny look… probably the same look you are giving the computer screen now.

Wikipedia defines backpacking as:
“a form of low-cost, independent international travel. It includes the use of a backpack or other luggage that is easily carried for long distances or long periods of time; the use of public transport; inexpensive lodging such as youth hostels; a longer duration of the trip when compared with conventional vacations; and an interest in meeting the locals as well as seeing the sights. It is typically associated with young adults who generally have fewer obligations and thus more time to travel.”

Backpacking Chicago
Jay Pritzker Pavilion Millennium Park

Although I was not traveling internationally, nor for a long period of time, all other aspects of this trip pertained to my visit to Chicago. I had not intended on “backpacking”, but I was on a tight budget and had a fear of driving a car in a city of 3 million. When you come from a town of 8,000 a city of 3 million might as well be 3 billion.

There were a few things about this trip that were going to make me step outside of my comfort zone:
1. Relying solely on public transportation
2. Carrying everything in a backpack and small cross bag
3. Going on the trip completely solo
4. Staying in a hostel

Backpacking Chicago
Nicknamed the L Train because they are elevated above ground

I think I was most nervous about the public transportation part of the trip as my prior traveling history was limited when it came to public transportation. I assumed I would get lost in Chicago… often. I was correct. The moment I stepped off the Amtrak and walked up to the street level, gazing up at the tall Chicago skyscrapers, I was instantly lost. I was arrogant in the fact that memorizing the maps prior to my arrival and my “cheat sheet” of transportation notes would be sufficient enough. I was wrong. My street map was of no help and I did not use my phone for walking directions – as I was running low on data minutes… damn you overages! In hindsight I wish I would have just paid the overage. But due to my recent job loss, saving money was in my best interest.

I walked so much during my trip that I had blisters on my feet (even with appropriate shoes on) and was hobbled around like a shameful creature. Getting lost had both it’s highs and lows. The highlight was proof in the kindness of people. After about an hour of being lost I got on the correct bus, only to find out that where I had got on was where I should have gotten off. A stupid mistake, but the bus driver was kind enough to drive off route to drop me on the correct street and told me which bus number to catch to get me to where I needed to go. My lowest point was on my last day. I was fed up loosing my way each day and I stood on a corner feeling hopeless. There were no people around to ask for directions and I felt my eyes welling up with tears of frustration. I gave myself a mental pep talk, told myself to pull it together, and eventually found my way thanks to a local, who magically appeared and directed me to the correct subway line.

My next hurtle was carrying everything I would need in a 30L backpack and small cross bag. A true backpacker can probably laugh at my neediness for more packing space. Especially as I was only gone for 6 days but as a road tripper I am accustomed to at least a medium sized suitcase. And that suitcase being carried around in the back of my car as opposed to on my back. I had different accommodations each night while in Chicago so leaving my bag with the hotel or hostel was not an option. Prior to my arrival I was worried about sticking out like a sore thumb carrying my bag on my back. I was relieved on my first day as I saw many backpacks and wheeled suitcases being dragged around as I walked to my hotel. Aside from a tired back it really wasn’t that bad.

My next step was that I had never traveled completely solo before. I had either departed with my travel companion, met a friend at our destination or Boomer tags along with me. Some may believe me traveling with Boomer is solo traveling but I disagree. Anything that travels with more luggage than I do is a travel companion.

With the combination of solo traveling and public transpiration I knew I would be putting myself to the test with both of these challenges. Since my trip was short I never felt any effects of loneliness, however I am an only child and I am accustomed to doing things on my own. It was interesting to me however when people realized I was traveling alone as it evoked curiosity. While in Chicago waiting for a bus I chatted with a couple of fellow tourists. Once we got on the bus we parted ways… briefly. The wife left the seat next to her husband and sat next to me, bluntly asking “I need to know why you would travel to Chicago by yourself”. Her inquisition was in no way meant to offend, but she wanted to know why a girl from Idaho would travel to Illinois by herself. I obliged her with the answer of life is too short to wait around for someone to go with you. If you want to go somewhere, then go. Don’t wait as it may be too late.

Backpacking Chicago
my Westernized hostel room

My last step was my biggest leap. A hostel. Yes it was “Westernized” and I did rent my own room as opposed to sleeping in a bunk but I was not about to Thelma and Louise myself off a cliff. I had stayed in a shared bunk space before during hiking excursions in Canada with my Dad. From that experience I knew enough to book my own room.

Backpacking Chicago
All my crap that I lugged around Chicago

It did cost about $40 USD more but it was about $180 less a night than the hotel I had been staying at. In addition to the savings I did not have to deal with being woken up by people as they came into the bunk room. I’m a light sleeper and it takes me forever to fall asleep. My only complaint was a girl (who I assume was drunk) running down the hallway at 1 am yelling about how someone was mean to hear. This of course could have happened anywhere and she was lucky I wasn’t bitchy enough to be one more mean person to her that night.

Looking back on this trip I did have an enjoyable time, regardless of a few of the complaints above. Visiting Chicago was a great experience and I ticked off a few things on my bucket list. I also tried a few things that I rarely see on the West Coast, such as Chick-fil-A. I wasn’t impressed, sorry Mid-Westerners and East Coasters!

Backpacking Chicago
Deep Dish Pizza

I also had my first deep dish pizza from Giordano’s. The deep dish was good, but not really my style. I also impressed the waiter by how much of the pie I ate that night. Hey – I don’t keep this “svelte physique” by eating just salads.

Backpacking Chicago
Mamma Mia Broadway Show

I also took in a Broadway show. It was not my first show but it was my first one in a major city. I saw Mamma Mia, a show I had never seen before but I had watched the 2008 movie with Meryl Streep. I enjoyed myself but I do always have a question… why the hell do certain audience members always feel compelled to sing along? Great you know the words and you love the songs but I did not pay to hear you sing, I came to hear the performers sing. You don’t hear me belting it out at a Bon Jovi concert because I know every word that beautiful man sings, do you???? No, I let Jon sing it because that’s his job and he’s really good at it.

Now if you will please excuse me I need to go listen to some Bon Jovi.


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10 replies on “I Backpackish Chicago”

I’m happy that you stepped outside of your comfort zone and went on a vacation that you really wanted to see, and didn’t wait for someone to travel with you! Sorry that you almost ended up in tears at one point, but I think that we’re able to learn from experiences like that, and they make us tougher! 🙂 Thanks so much for linking up with #WeekendWanderlust this week and we hope to see you back again next week!

Chicago is a great city but can be a little overwhelming when traveling solo. Nothing like a good deep dish pizza to make you feel better. We saw Mama Mia here in Florida, and it was one of my favorite musicals. Bon Jovi grew up only a few blocks from my grandmothers house. Thanks for being part of #WeekendWanderlust.

Chicago is one of my favorite cities in the world, but it can definitely be intimidating the first time around. In fact, every new city I visit gives me a momentary “oh crap” moment — usually over the public transportation system. It’s just different enough everywhere to give me a fresh heart attack each time I try to figure it out.

Still, Chicago is definitely an amazing city, and pretty good one to use as a way to step out of your comfort zone. I’m glad you had a good time! Thanks for linking up to #WeekendWanderlust!

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