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Plan Your Trip to the Windy City of Chicago!

January 12, 2020 3 min read No Comments

Are you ready to taste some pizza that will put nearly all other to shame? Or try a hot dog that is paired to comparison as the hot dog stands in New York? Delicious Italian food or visit Portillo’s? All of these things can only be done in the great city of Chicago!

Now there is more to do in Chicago than just eat food, though there is an amazing selection around the city for special “Chicago styled” foods that you can’t find anywhere else.

Get lost through the streets of Chicago, you will be amazed by the architecture that is so widely diverse from block to block downtown. Most notable are buildings like Willis Tower, Radisson Blu Aqua Hotel, Tribune Tower, Wrigley Building, Chicago Water Tower and of course Cloud Gate. If these buildings could talk you could would hear some amazing stories.

Now you might also be thinking about Chicago as a big gangster city, and you are right! During the Prohibition when alcohol was banned in the U.S., Chicago gangsters, like Al Capone and Bugs Morgan, took advantage of this. Running liquor from Canada and selling it across the country. This, of course, was known as bootlegging, and it was a very lucrative business for these Chicago gangsters. Illegal drinking institutions, called speakeasies, began popping up across the country. Most famous speakeasies were in big cities like Chicago, New York, Atlanta, and San Fransisco. These places got alcohol either from making it in the backroom – bathtub gin became a common method – or by purchasing it from very dangerous characters, like our gangsters and having it shipped in crafty methods.

Trust me, you’ll want to experience a speakeasy while you are visiting in Chicago (if you are of age of course). There are many to choose from that are still held to historical standards of hidden doors and passwords but some of the best ones out there, The Ladies Room, Violent Hour, The Pub, The Drifter, Room 13, Watershed. There are a few options, but you might need to know someone to get in there. They try and keep the original integrity of a Speakeasy.

Continue your trip down to the Navy Pier. This is an iconic location that dates to the early 19th century and popular destination throughout much of its history. Opened to the public in 1916 and was originally named the “Municipal Pier,” now what is called the Navy Pier was built under nationally-known architect Charles Sumner Frost based on Daniel Burnham’s “Master Plan of Chicago.”

If you enjoy live music and art shows then you have to visit Millennium Park. In Millennium Park you can catch a movie screening in the summer, folk concerts in the summer time or in the winter you can skate through life on the ice rink at McCormick Tribune.

We talked about the food locations in Chicago earlier – well if you are a foodie, or just looking for a taste of Chicago that is original to the city and the culture of this city we have a few places in mind for you. At Portillo’s you can pick yourself up the original Chicago-styled hot dog and the dressings on this dog don’t include ketchup. Order a slice at Uno Pizzeria & Grill, a Chicago mainstay since 1943, this is the best pizza in the city! End your Chicago meal with dessert at The Original Rainbow Cone, this is the oldest ice cream shop in the city, established in 1926.

If you are a baseball lover a trip to the Windy City isn’t complete without a trip to the baseball field. Try to catch a game and or maybe a ball at Wrigley field or Guaranteed Rate Field. Both located in the city limits of Chicago, you won’t be disappointed heading out to watch a game of either the Chicago White Socks or the Chicago Cubs.

Day or night – the best way to see the city without having to worry about traffic, blinkers, finding parking or paying for it for that matter, are Divvys. Divvy is a Chicago bike share program where you can see the city with ease, carefree and you don’t have to haul your own bicycle. There are stations where you can pick up or park all over the city.

Whatever your plans are for wandering around Chicago – I hope these tips help you have a full experience in Chicago!

Traveling 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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