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Cigar Shops…

March 27, 2015 5 min read No Comments

Greetings from the Windy City!

I am so excited to be back in Chicago! I haven’t really been here and spent a lot of time since I graduated Boot Camp and went over to “A” school. I love this city, I love the history, the culture, the architecture and the food! Now I can’t say that I have seen all there is to see in the city from previous trips through but I will say that I have seen a bit this city has to offer and yet I am always finding something new even in places I thought I knew.


We have spent a few days on more the out skirts of the actual city of Chicago and I got to experience my first experience of true Chicago food in years! I was taken to a chain of restaurants that originally started as a single hot dog stand near the Navy Pier, called Portillo’s! When I walked through the front door of Portillo’s I felt like I walked into a time capsule that preserved the 1920s. The swing jazz music being played over the PA system, I loved how every employee was wearing a newboy cap and the walls were decorated with items you would have seen and used in everyday life in the 1920s.PAH_6490

My next adventure in Chi-Town was one an adventure that I will never forget. Have you ever had those spur of the moment decisions to do something completely spontaneous and out of the ordinary? That was my adventure Saturday night. It started off like any other night when you have a large group of people all trying to figure out what to do for the night….”I don’t care either way”, “I’m up for whatever”, “You guys decide I’m in”…aka completely unproductive. It took a while but we finally decided to go with my idea to go find a Speakeasy.PAH_6513

Speakeasy is a bar that during the Prohibition years were hidden all across the city. They were hidden in basements, attics, storage facilities and basically anywhere where they could be hidden away and only be found by someone on the “inside”. Driving into Chicago I was surprised to see the lack of traffic going into the city on a Saturday night, it basically took us no time to drive past the Shad Aquarium and towards the Navy Pier. After finding a place to park we set off on foot into the city!


Seeing the city skyline is nothing short of breath taking and when you see it at night it is even more astounding. Even if you don’t like big cities, even you could appreciate the architecture genius that goes into laying out a big city while still preserving the historical buildings throughout Chicago.

We went past the Millennium Park Ice Skating rink and found our way under the famous Chicago “Bean” Cloud Gate. I have always found the “Bean” to be an amazing engineering feat! You could take pictures of the reflection of the city against the metal and after two hours you still wouldn’t be able to capture every angle. Now I didn’t try to capture every angle but I did capture a few of them.PAH_6526

I could have walked around the city all night (though I don’t think the rest of my party would share my same sediment). My favorite part of the city is how the subway tracks are built above the city streets, listening to the train roll through the city “ca-clack, ca-clack, ca-clack” echoed off of the blacked out store front windows and interrupted pedestrians trying to hold a conversation as the train passed above them. I have been to a lot of cities in my life and yet Chicago is one of the unique cities for this engineering design alone.PAH_6561

We finally made it to our stop, the “Bassmen”. I thought that when the GPS told Blaster that we were there he was just lost. But we turned the corner and you saw a cigar shop built into the side of another restaurant, finding that to be strange the image was complete by two greased back security guards bundled up against the howling wind with trench and peacoats standing on the street corner looking suspicious as ever. I finally found the only job in the world where you are being paid to look suspicious! PAH_6586

Blaster went up to them and said some type of secret password, they radioed down to see if we were clear. Once we got the okay the second security guard opened the secret door and let us inside. Walking in it was nearly blacked out in the entry way, making me feel slight disoriented. We walked through the black velvet curtain to see the coolest jazz bar I have ever seen! They definitely were trying to keep the atmosphere as true to the original Speakeasies as they could.PAH_6598

Tea light candles on every table, antique chairs with metal backs, the attire being worn by the staff and the sound barrier ceiling to silence the noise to the outside walls to ensure the location’s secrecy. I was absolutely ecstatic about actually making it to a legitimate replica Speakeasy. Once we had our fill of the overly priced drinks we kept walking, till my friend had the brilliant idea to rent bicycles and ride around the city! This was the best idea I have heard almost all year! I am so happy that everyone else wanted to as well because if they didn’t I probably would have gone anyways. It really does change the entire experience of traveling around the city, it adds a level of wonder and excitement that wasn’t there before.PAH_6565

Eventually we ended the night at Exchequer Restaurant & Pub. This is another location that is slightly iconic to Chicago history. This restaurant was established in the early 20’s and was the graced by the presents by their patron Al Capone. During the Prohibition this was one of the original Speakeasy locations known as “226 Club”. Now it s home to some of the greatest Chicago style pizza I have had…probably ever.  All in all it was a great day and really exactly what I needed, since acquiring a school bus on the tour and leaving my poor Luna (my car) in Florida my photo excursions have basically come to a grinding halt. So having an adventure like this is exactly what the doctor ordered for this crazy photographer. PAH_6617PAH_6683Traveling Photographer Out!


The things I love the most...Wine, traveling, and photography! Join me on my adventures as I travel the world and share my experiences as I travel with my daughter, top places to visit and how to travel on a budget!

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The Backpacker Mom

Hey there! I'm Phylicia, but you probably know me as "The Backpacker Mom." As a passionate wine educator and travel blogger, my daughter and I embark on exciting adventures around the world, sipping wine and creating unforgettable memories together. Join us on our wonderful adventures around the globe! Read More Here

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