My Solo Chicago Trip

My solo trip to Chicago was full of good food and a lot of walking around the city seeing some of its landmarks. And it ended with me spending time with my little sister and I saw one of my favorite band’s 10th-anniversary show. This wasn’t my first time visiting Chicago, but my first time getting to explore and see the city. So here’s how my solo trip to Chicago went and what I saw and ate.

Donut, Donuts, and Donuts!

While I was in Chicago, I started each day walking down to one of the local donut shops. The first donut shop I went to was the Doughnut Vault. It was a ten-minute walk from my hotel but turned into a 40 min walk. I ended up walking past it twice before I found it, and it was well worth all the walking I did to find it. It’s inside of an old bank vault and has some of the best donuts I’ve ever had. I bought an apple fritter, an apricot jelly-filled donut with vanilla frosting, and whiskey caramel pecan old fashioned donut. Which was all their special for the day and boy were they good.Chicago Donut Vault

The following day I walked down to Stan’s Donuts & Coffee after a not-so-great breakfast at my hotel. They had a wide variety of donuts to choose from, but I didn’t want to order more than one again. So, I bought their pistachio glazed donut and a cup of tea. I’m glad I ordered the tea to go with it because the donut was sweet. And when it comes to sweet things I like to have a hot drink or a cup of non-dairy milk on the side.

Chicago Stan's Donuts

My last two donuts shops were The Dapper donuts and Do-Rite Donuts & Coffee. The Dapper Donuts does mini fried donuts with your choice of toppings. I ordered their Strawberry Bella, which is their fried donuts topped with a strawberry sauce and graham crackers. Since their donuts are fried they have a nice crisp on the outside and are warm and fluffy on the inside. With the toppings, it reminded me of a strawberry shortcake. If I wasn’t visiting, it would be something I would order, take home, and eat with a side of ice cream.

Dapper Donuts & Do-Rite Donuts

My last donut shop was Do-Rite Donuts & Cofee. There’s also Do-Rites Donuts & Chicken where you can get a chicken sandwich made with a donut. But, since I don’t eat meat I visited their only location that doesn’t offer it. When I walked in there was a line so it gave me plenty of time to look over my options. I decided to have their Michigan Apple Fritter. Since I got there the donut was still warm. So I hurried to the river walk so I could eat it while it was still warm.

After trying four different donut shops my final ranking is Donut Vault at the number one spot then Stan’s Donuts for second place, with Dapper Donuts and Do-Rite Donuts tying for third place. If you’re ever in Chicago I would recommend checking out Donut Vault they sell out so make sure you get their early so you can try some of the best donuts.

The Bean

You can’t visit Chicago without checking out the iconic bean. So, my first full day in the city I walked 30 minutes down to Millennium Park to see The Bean. My favorite part about visiting Millennium Park and seeing The Bean was hearing all the different languages and accents. Around The Bean, it was a giant melting pot of different cultures and people had traveled from miles away to see this iconic Chicago landmark. I thought it was cool how a silver blob that looked like a bean could bring people together.
Chicago Bean Landmark

Food!

When I travel I have one rule and that’s no major chain restaurants. There’s nothing special about major chain restaurants they are all over the United States. My only exception is regional chain restaurants since they are only found in certain areas. So when I planned my trip to Chicago my goal was to eat at local restaurants.  My first stop was Kuma’s Corner off Belmont Street for an impossible burger. This restaurant was mentioned by someone on Instagram as one of their favorite places to get a burger. So I checked out the menu and say that they had an impossible burger and decided to give them a try. I had the Converge which is an impossible burger patty with Cherry tomato jam, avocado mash, cheddar (V), roasted garlic mayo (V), baby arugula, red onion, on a pretzel bun.
Kuma's Corner

The next day I did more walking and site seeing than eating since it was going to rain the following day. For lunch, I ate at Native Foods Cafe. I had their orange cauliflower which breaded and fried cauliflower breaded, fried, and tossed in an orange sauce. Then served on fried brown rice. It was delicious and something I could see myself making at home for lunch or dinner.
Native Foods Cafe

Since it rained most of the day on Friday I didn’t want to venture out too far. So I went to The French Market since it was only a block away from my hotel. There was a lot of good food to choose from there and I ended up eating at Vegan Now a vegan soul food stand. I had their jerk chicken, BBQ ribs, kale, and mac and cheese. It was all delicious and my favorite part was the jerk chicken it had a kick to it. So, afterward, I went over to Vanilla Patisserie for dessert and cool down from the spice of the jerk chicken. They had a lot of sweets to choose from and I ended up getting a pumpkin cheesecake that was satisfied with my sweet tooth and cooled down my mouth.

On my last full day in Chicago, my little sister drove up to spend time with me and see the concert later that day. We ended up walking down to the Nutella Cafe. I’m not crazy about Nutella and the idea of a whole cafe centered around it was a little strange. I ordered a hot tea and my sister ordered pancakes with Nutella, strawberries, and whip cream. I didn’t much care for it since I’m not a fan of Nutella. Afterward, I grabbed dinner at the Veggie Grill. Since I hadn’t been eating the healthiest throughout my time there. I decided that I’d have the taco salad instead of a burger or sandwich.

All the food I tried during my visit was delicious. Well, except for my hotel’s breakfast buffet, but I expected that. I didn’t have a favorite and would have everything I tried again.

Chicago’s Navy Pier

The day I had planned to visit the Navy Pier was cold and wet. Ideally, I would have liked to visit the pier during the day, but it didn’t stop raining until around 5 pm. It was an hour’s walk from my hotel so by the time I got to the pier the sun had already set. Though I didn’t get to see it during the day it was nice to see the city at night. I walked around the pier and took photos. Then sat for a while in the crystal gardens, before walking back to the hotel. In the future, I’d like to visit Chicago again, and hopefully get to see the pier during the day. Chicago Navy Pier landmark

NSP’s 10th Anniversary Concert

NSP is one of my favorite bands, and I didn’t want to miss being there and supporting them for their 10th anniversary. The line up for the show was Planet Booty, TWRP (Tupper Ware Remix Party), and of course Ninja Sex Party (NSP).

I went with my little sister, the venue didn’t allow backpacks. Both my sister and I use small backpacks as purses. So, we ended up going back to my hotel to drop off our bags, and when we got back Planet Booty was almost finished with their set. Afterward, I learned that they do allow backpacks of a certain size and if it’s a large backpack it must be clear. So, we went through all that trouble for nothing. But despite all that I still had a good time at the show.NSP's 10th

Before their set, they played a video that showcased their 10-year career. Then they came out with TWRP and played songs from current and past albums. They played a song off a cover album they’ll be releasing soon. It was wonderful getting to see them in concert and a great way to end my trip.

Overall, I had a great time in Chicago even though I was there by myself. I explored the city, tried different donuts, and ate lots of good food. And I couldn’t think of a better way to end my trip other seeing one of my favorite bands hit the 10-year mark.

Related post: Dragon Con Recap

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Angela Louise
Written by Angela Louise
Angela is the owner and chief content creator for Weird Louise and is working towards becoming a full-time blogger. In addition to blogging here on Weird Louise, she is an artist and owner of the Social Awkward Club. She also has a passion for helping others discover ways to live their best lives.