Throwback to my first solo trip: Chicago, 2015

A new year’s throwback and encouragement for you to try something new this year, like solo travel. Start small and build from there. My ticket to Chicago was $80 and the AirBnB was quite affordable as well. Take a chance, trust yourself. But first, reminisce with me.

Chicago. My solo trip to somewhere I've never been. I'm planning on doing this at least once a year. Within the first few hours of my arrival, I chatted (in Spanish) with an older Puerto Rican lady on the bus. Even though she was fussing at someone else in the process...there was something welcoming about it and I claimed it as the first win of my trip.

Also on my first day in town, I got terribly lost getting to my Airbnb. Yes, I rented an Airbnb for the first time on this trip-if you’re going to plan an experiences trip, go all the way with it.

So yes, completely lost-with my bags, of course. At first, everything seemed like it was going well. I was successfully following the CTA transit directions on an app I downloaded. Mistake. The app didn't tell me which way I should be going on said transit once my route switched from train to bus. Just what bus I should be on. Soooo....naturally I got on the right bus in the wrong direction and an hour or so after I'd told my Airbnb host that I'd be by in 40 minutes to drop my bags off...the bus I was on turned around. It hit the end of the route and just completely turned around. Umm...WAIT, WHAT?? So...I quickly got off at the second stop on this return route, then deleted the app. I wandered for a bit, saw a ramen bar I quickly put in my notes to come back and visit once I got my life together and decided to just call a cab-hailing one proved essentially impossible. They just ignore you. So I call the first one that popped up in my search, and the dispatcher was rude as hell. She proceeded to tell me that it would be at least 40 minutes before anyone arrived and that they couldn’t guarantee anyone would even show up and to just look out for a maroon car. W...T...F?

Then I saw cars with Uber stickers and a light bulb went off. THEY HAVE UBER HERE! DUH! Up until this week, there was no Uber in San Antonio. City officials have been fighting about it for months...being greedy and ridiculous yada yada. So I downloaded the Uber app as quickly as my little fingers could go, went through all of the steps and within minutes I was in and had requested my Uber. BOOM. I was at my Airbnb within the next 30 minutes. Problem solved.

By the time I got there though, check-in was just an hour away so I dropped my bags and did a search for food. Straight up…”food near me”. The first thing on the list was a Cuban sandwich restaurant. Done and done. I headed out to waste an hour. My first experience being a “local”. I mean, I basically had my own apartment and I was walking to my destination. Total local. It started drizzling, but nothing crazy. I arrived at El Cubanito and salsa music was playing. Second win of the day. I ordered an egg, ham and cheese sandwich, a cortadito, a bottle of water and a Malta India, which I ordered in a moment of excitement when I saw it in the fridge behind the cashier. I was hungry and apparently wanted to bounce off the walls. Once I ordered both a cortadito and a Malta, I realized it was a bad idea, but I didn’t care. I was on a mini-vacation. Plus I’d need the energy for my explorations for the rest of the day. Am I right? Holler if you hear me.

I ate my delicious sandwich, drank all of the caffeine and headed back to my apartment. Sat down for a few minutes, because worn-out, freshened up, changed and headed out. It was my mission to visit 360Chicago. I HAD to do it. So I figured out my transit track directly from the CTA website, got on a bus then a train and headed downtown. Once I got to my stop, I was ready with headphones in my ears, secretly giving me walking directions to my destination. Made it to 360Chicago, looked up at the building in awe, smiled and headed inside. I waited in line for just a few minutes, asked for “one please”...and was told there was full overcast. Zero visibility. This was not a win. But I have to give credit to the ticket salesmen/women, who were honest enough to tell everyone in line that there is zero visibility, but tickets are full price. Sooo you’re paying full price to see absolutely nothing. I thanked them and headed out, unsure of where I wanted to go next. On my way in, a guy on the street had given me a flyer to a comedy show at The Comedy Bar. Luckily I didn’t throw it away. I put in the address, took a train and purchased my one ticket for the show. Because why not? There was no agenda on this trip, nothing was planned. I was doing as I pleased when I pleased for the weekend. I sat at the bar, had local beer and an order of fries (yep, just fries) and enjoyed an evening of pretty good comedy. It ended around 9:30p and since I wasn’t yet familiar with my surroundings, I decided to end my exploration for the night. Realizing I hadn’t packed any of the 7 pair of flip flops I own, I made my way to a Walgreen’s nearby and after having to wait for a very nice associate to find the last pair in the building for me-a sassy purple pair with “Chicago” in yellow comic sans type all over them, I hit up Uber again because I wasn’t fighting with transit anymore that night. It was getting late and I was growing tired.

On day two, I started with ramen, because what could go wrong after that. I went back to Jinya Ramen Bar-the one I’d seen while I was lost-and it was everything I could have wished for. Just everything. It made me briefly forget that my right foot was starting to hurt a bit. But I treaded on and tried 360Chicago again. Still overcast and zero visibility. Still full price. So I headed towards the Art Institute of Chicago. Let me just say that this museum is HUGE. I don’t even think I made it to all of the corners of art and amazingness. I saw the main exhibits and made sure to make it to the section with tiny rooms. Literally-tiny, detailed rooms only a little bit larger than a shoebox. There was something extra special about those and I loved them very much.

I also made it to the bean, because that’s a must. Also, I had no idea it would be in my path to the museum, so that was a win.

Once I managed to find an exit to the museum-which happened to be out of a completely different door than I came in, I decided I deserved a cup of coffee from a Chicago Starbucks. I walked in, looked in awe at their “after 5pm” menu and calmly ordered a venti iced water (I was SO thirsty) and a tall flat white (why does anyone order this in a larger size?). While I waited for my caffeine, a young woman approached me to watch a movie trailer and take a survey. There was a Starbucks gift card in it for me and again...no schedule...so naturally, I said yes. I can’t say what movie it was for or anything though, I agreed that I wouldn’t say anything specific about the movie on social media or the interwebs...about 25 times.

So moving on…

I went back to the Airbnb to rest for a minute, changed into warmer clothing for the evening and headed out to experience deep dish Chicago pizza. After doing extensive research, a place called Pequods kept popping up. Something about caramelized cheese in the deep dish crust...I was intrigued. I hopped on the correct bus and got off at the correct stop. Once I got there, walking directions in-ears, I was taken down a mildly sketchy sidewalk...and then under a very sketchy bridge...and once I walked about oh, .75 miles I arrived at my destination. The pizza was AMAZING. I only tried two different pizzas while I was there-this one and the original Gino’s, and this one was the best, hands down. I ate my entire personal pan, had a few glasses of wine and slowly won all of the bartenders over. One by one, the girls’ shifts ended and they went from the serving side of the bar to the drinking side of the bar-and sat next to me. They chatted, asked me if I lived there (flattered), and when I said no asked me what I was in town for (just visiting)...etc. I asked them what people there do on a Sunday night. Like, is anyone out or is everyone in getting ready for the week? How responsible are Chicagoans?

They discussed a few different places, one of which quickly got shot down because one of the girls described it as “kinda rapey” and ultimately directed me towards Boiler Room, a bar that has Jameson. Infused. Soft. Serve. That was all they had to say. That was my next stop. It was a straight bus ride down the street. Off I went to have my spiked soft serve.

Luckily, this bar was basically under the blue line train. Which was perfect, because I was on the blue line. I went in and had to wait a smooth 20 minutes for the train to actually arrive. It took SO long. 

20+ minute wait at California Station

Then I got on the train and soon realized the stop I needed wasn’t on the route. I got off at another stop that had the name of one of the streets near the apartment in hopes things would look familiar. Not only did they not look familiar, but it was the sketchiest train stop I’d seen thus far. I swiftly exited the train station (after being extremely hesitant) and headed to the other side in order to go in the opposite direction, at least to a safer looking stop. I was tired and getting annoyed with this whole situation. I got off at the next normal looking stop and called Uber to be rescued yet again.

By Monday I was pretty tired. On day one I logged in around 9.5 miles of walking, day 2 was milder with about 6 miles. So by Monday I JUST wanted to go to the observatory. But I called and they said there was overcast, but it should clear up around 2pm. Again I started the day with ramen, this time at an amazing place called Furious Spoon. The place was nice, welcoming, fresh ramen, good sake (a little expensive, but good) and hip hop music. All the good stuff, too. I’m talking the Roots, Common, Fugees...all the greats. I lollygagged until about 2:30, then took a stroll around the neighborhood I was in (super cute!). I also called the observatory again and was told there was still overcast but it should clear up around 4. My right foot was really starting to hurt. Just the one. After I walked around a bit and ended up limping a little, I boarded the train (the right one) and headed down to the observatory. Overcast. Again. WTF. So I said ok, fine. I guess this won’t be happening on this trip. I proceeded to go to Macys because I was pretty much full on limping. This was in part my fault because I took Chucks on this trip. No support. Never had a problem though. But oh bitch was it a problem now. Nothing in Macy's...so I headed to Sports Authority and picked up a pair of high tops from the kid’s section. Relief for my arches and right foot, but still not 100% comfy. I was growing more and more over it. I literally just got on a bus and rode it to sight see...saw the shoreline and rich part of town, got off at a bus stop and waited for a random bus with some older women. Rode that one to sightsee a little more...then got off and got serious...it was time to eat.

I headed out for the last time to have something to eat and went to Gino’s East. The real deal, right? I had an old fashioned (I don’t think the bartender knew how to make one really) and 40 minutes later out came my small pizza. The crust was super thick, but it was delicious. So much cheese.

That was my last adventure in Chicago. I proceeded to take all of the proper trains and buses, and got back to the apartment in one piece.

The next morning, I got up bright and early at 5am for 7am flight, Uber’d it to the airport and came home to Texas sunshine and heat and slept in my own bed again and all was well in the world. Another trip of experiences in the books.

Until next time, travelers, dreamers and soul searchers…

Peace, love and travel to all!

Originally published in October 21, 2015 to the original sdotcurls.com on Blogger (a true throwback!)