Chicago is probably my favorite big city. Every time I have been there I have a great time. I have been a few time before this trip but it has been eight years.
Eight years ago I stayed with my cousin in her dorm and she took me around to all kinds of really cool spots. Before that, my trips there were with family and we did all kinds of tourist activities.
This trip I was determined NOT to do any touristy things. I had family and friends who might as well be in the city. I really didn’t give a fuck what we did, I just wanted to spend time with them! So that’s exactly what I did.
I showed up in Chicago the same day as Cindy and her mom. They had planned to stay at my friend Justin’s apartment by he was still out of town. I tagged along with them. I told his roommates who I was and how we met in Taiwan. No problems, slept on the couch.
The next morning my cousin picked me up to drive out to Naperville to see her mom. Cindy was leaving to Minnesota for a couple days and Justin wouldn’t be in until for a couple days. I had nothing better to do then go to the suburbs. But, I am super grateful that I did.
We stayed up all night with her mom drinking wine, eating cheese, and talking about our family history. I learned a lot of things that I hadn’t known. It really puts certain family situations in perspective.
The next night, we had dinner with my cousin’s boyfriend. After that, we went to a bar and played darts. I almost won my first game. Does that count for anything??
The next day, a Friday, I was alone in Chicago. Everyone I knew was either working or not in town. A made myself vulnerable and tried out Couchsurfing’s new Hang Out function.
It was a great experience. I think I met up with the group at around five p.m. and ending up closing a bar at 4 a.m. Couchsurfing makes it easy to never travel alone.
One of the guys I met was named Darren. He was interested in going out approaching people and meeting girls. I told him the truth, “I am down to go to talk to people, but I am awful at approaching strangers.” “It’s easy,” he said.
He told me, “just go up to this group and ask them what a good bar is.” Before I could come up with any excuse not to, he literally pushed me into them.
We went from bar to bar doing these all night until I left him to go to sleep. I learned a lot from him. It actually is no big deal to approach strangers in a bar. Everyone seemed quite happy to talk. This is not something I have personally experienced in my life before.
I’ve led a shy existence. But, that is changing.
The next day, technically it’s the same day because I went to sleep at 4:30 A.M., I met up with my friend Justin. He had another friend he met in Taiwan, Carina, visiting too. We all went out for a late breakfast. Justin had to go work. I wanted to go to the Lincoln Park Conservatory to see the plants. Carina came with me.
After the Conservatory we rented some bikes and rode by the lake. This was such a relaxing way to spend the day. It reminded me of the bay in San Diego. I wanted to go home and make a point of riding along the bay regularly. (I have not done this.)
The plan was to meet up with Justin for dinner. But apparently Carina is just naturally late. Justin told us to meet 30 minutes early so we would be one time. Fantastic! They went to a play and I went back to my cousin’s to get cleaned up. We met up for drinks after.
Ended up getting drunk. Getting hungry. And, dropping a watermelon in the grocery store. I also through a cantaloupe at Justin while he was trying to sleep. I went to bed at 4 or 5. Two hours later Cindy showed up.
She had pie from Justin’s mom. She feed it to me while I was barely awake. Life can be good sometimes. 😉
I spent the next two days doing some touristy stuff with Cindy and her mom.
I took only four pictures. Mostly of Lego versions of the Chicago skyline.
And a fat Tinkerbell graffiti piece.
Chicago was wonderful.