“Going to Chicago was like going out of the world” ~Muddy Waters

“Going to Chicago was like going out of the world” ~Muddy Waters


Spontaneous Travel:

I planned this trip less than 24 hours before I landed in the wonderful city of Chicago. Why did I decide to go? Well, let’s just say it was a rough week and I needed a break. I was on a budget of course and one of the reasons I booked this trip was because the plane ticket was so cheap! I was hesitant about doing it because I didn’t have a place locked down as to where I’d stay, but I thought, “What the heck! Let’s do it!” I have gotten lucky a few times doing this the day before and I recommend that you keep looking for tickets directly from the airlines or even third party sites like Expedia. Flight was booked – now on to where to sleep for the weekend….

Where I Laid My Pretty Little Head:

I was looking around for about an hour before the panic started setting in. As you can imagine, staying in the downtown Chicago area and booking the day before is not cheap. Then I stumbled upon the Freehand Chicago (http://freehandhotels.com/chicago/). This is not just a hotel, but also a hostel. They accommodate both hotel suites and coed or all female shared rooms. Let me tell you that I did my research on this place! I was a little nervous, but adamant that I wanted to stay downtown. This place had EXCELLENT reviews and after talking to a few friends of mine who have stayed in hostels before, they agreed this was a good one. I paid just $40 per night (I know, how incredible for downtown Chicago) and they had lockers there, too, so I could put my duffel bag and laptop safely tucked away. The room was extremely clean, welcoming with a warm hipster theme. It had two bunk beds, a small couch and one bathroom.   

More About Freehand Chicago and Broken Shaker:

The staff at Freehand were outstanding! Super friendly and accommodating are words I would use to describe all of them. I made friends with my bunk mate Daniela and we hung out all weekend! It was so fun to have a friend to show Chicago to and explore with. One of the most exciting things Freehand offered was a free two hour tour on Saturday morning that Daniela and I went on together. We saw so much in two hours and learned even more! They offer a free standard breakfast in the basement level of the building, which consists of an assortment of fruit, bread for toast and a variety of cereals.

On Friday and Saturday nights, they offer an assortment of tacos, something they call Tacoteqa. Because I ate my weight in pizza, hot dogs and chocolate, I wasn’t super hungry, but I made sure to interview some of the other hostel stayers who ate them and they assured me they were the best tacos they ever had. They said they were full of flavor! Next time, I’ll be sure to be hungrier so I can have them.

I did indulge in an adult beverage, however. After a long day of walking, I was excited to head to the Broken Shaker (http://freehandhotels.com/chicago/broken-shaker/) and check out what it was all about! I got a margarita and it a very good! Garnished to perfection and shaken just the way it’s supposed to be. The vibe in the Broken Shaker was super laid back and wasn’t the rushed atmosphere that I was used to. I met a couple from Colorado and we chatted for a few hours. This is the experience I’d hoped to get out of staying in a hostel. I didn’t want to a hermit of sorts. I wanted to make sure I interviewed people, got to know them and where they were from. When I asked the people I was speaking to why they chose the Freehand they said they were drawn to it by price, the location, the awesome reviews, or a mixture of any of these. I am so happy I found this place!

Donuts, Pizza, and Dogs – OH MY!


Anyone who knows me knows that I have a fascination with donuts. Why? I think it has something to do with nostalgia. Remembering childhood and how happy you got when you were able to have a donut. Also, now that I’m an adult donuts are made more creatively than just a Dunkin Donuts shop or something generic like that. I like creativity and value mom and pop type shops when I want something good for my soul. Do Rite Donuts (http://doritedonuts.com/) has two locations in downtown Chicago and I’ve been to both. Both locations are tiny, but you aren’t going there to open your computer and hunker down for hours on end as if you’re in a Starbucks. No. You’re going in there to indulge on delicious morsels of heaven. Otherwise known as donuts. I found this shop by accident in August 2016 and have not stopped talking about it since. I may own a t-shirt from this shop as well. What can I say? I love it! When I became friends with Daniela on our first night at Freehand, I said, “We are getting donuts.” It wasn’t a question. It was a fact. She was in! On Sunday, we walked over to the Loop and ordered.

When you make your way to Chicago after reading this blog and you find yourself in line at Do Rite Donuts, you MUST order a buttermilk old fashioned donut. After that you can order whatever you want. That must be the first thing you order. You haven’t lived until you’ve tried that one. Be a tourist and take a picture with the donut outside of the W. Randolph location, too.



Since I’ve been to Chicago previously, I’ve had already tried 1 out of the 3 biggest Chicago pizza eateries there are. This previous time, I tried Gino’s East and Connie’s Pizza. In comparison, I would say that Connie’s Pizza was incredible over Gino’s East, but I also really love Giordano’s Pizza.

Giordano’s (https://giordanos.com/locations/gold-coast-magnificent-mile/) does tend to get super busy around dinner time and the wait times can get long. They also do not serve food at the bar, which is something that was new to me. It was worth the wait for my take out though! Piled high with cheese, toppings and sauce, you can’t go wrong! I’d also recommend trying a side order of their meatballs. Flavorful and covered in sauce – it’s really a perfect starter before your pizza arrives.

Gino’s East had INCREDIBLE bar service (http://www.ginoseast.com/locations/superior#home). My bartender, Julio was very nice and attentive to everyone at the bar. He had extensive knowledge of the menu and made sure to give me updates on when my pizza was coming. Deep dish pizza does take longer to cook than regular pizza. Average cook time for authentic Chicago deep dish is about 45 minutes. I liked the flavors of Gino’s pizza, but felt is was slightly soggy at the bottom, making it difficult for the toppings and cheese to stay on.

Connie’s Pizza (https://www.conniespizza.com/archer-avenue/) is located more on the South Side of Chicago, which wasn’t really my favorite part. However, it was worth the Uber ride! Connie’s was Daniela’s idea and I’m glad we went. Upon walking in, you can tell it’s a family establishment. This location was built in 1985 and I knew families have gathered here for a while. Our service was great as we sat in the bar area. We decided to get personal sized pizzas with different toppings and crust options so we could each try something new. What a fantastic, cost saving idea! We each paid the same as the cost of one large pizza (after the cost of our drinks!). If you travel with friends, I would recommend doing this. It gives you all the experience to try new things! Daniela loved Chicago pizza and I obviously already adored it!

Chicago Dogs:

Now, let’s chat about Chicago Dogs. You know, the delicious, no-ketchup-having, mustard and green relish dressed, dog that has pretty much everything out of your fridge on it. Yeah, that. It’s pretty insane. I love them. The best place to get them in my opinion is Downtown Dogs (http://www.downtowndogschicago.com/). This was another authentic Chicago food Daniela hadn’t tried just yet. I always get mine without hot peppers, but if you love them, keep ’em on! They hand cut the french fries there, too, which is awesome. To me, this means the restaurant takes pride in what they are doing. Upon the first bite, your mouth can be confused about what’s actually happening. Pickle, mustard, hot dog, green relish, onions, tomato all nestled in a poppy seed bun. Wow! Talking about it makes me want one right now. Trust me. You want one.

Places you need to see:

Upon the completion of reading this blog article, after you book your stay at the Freehand Chicago and your flight, make sure you write these places down so you can visit them while you’re there:

Something I learned on this trip was to use the technology to its fullest! Daniela were all about using Groupon. For example, she wanted to go to the Chicago History Museum while I met a friend of mine for tea. Instead of her paying a $16 entrance fee, I found a $10 cost on Groupon as well as additional discount code, making her cost only $6.40! How crazy is that?! She was so excited we found that. I would suggest anywhere you travel to that you use that. You never know what you will find. Daniela saved well over $10 just by signing up and using a discount code. Simply type in where you are looking to go to see if there’s a discounted rate. I’d also suggest using UberPool if you are traveling alone or with one other person and aren’t in a rush to go somewhere. It’s A LOT cheaper and incredibly convenient!

Until next time, Chicago:

I hope you find this blog helpful and hope you’re planning your trip to the Windy City! Leave your comments below if you have suggestions for others about places to go or questions for me!

Happy traveling!