6 Things to Know Before Traveling to Chicago Alone

Are you planning to travel to Chicago and wondering where to start? Moving for the first time to a highly populated city like Chicago may seem overwhelming. However, with knowledge about the city of Chicago, you can, at any time, walk to Chicago head up. 

It is for this reason that we have decided to write this article for you. To let you know of the things in Chicago.

a city next to a water body/Traveling to Chicago Alone

Continue reading this article to find out more about the essential things to know before traveling to Chicago alone.


Are you planning to travel to Chicago with your light t-shirt and a pair of shorts? If so, then you’re in for a shock. One of the cities greatly affected by the winter season in the US is Chicago.

The city also experiences some rains accompanied by thunderstorms. The heavy winds resulting from the storms are capable of causing so many damages. It may even cause tornados.

The city also experiences other seasons like summer and spring. You should be sure of the type of season being experienced in the city before you travel there.

You’re advised not to visit Chicago during the winter season, as this may be dangerous for you.


While taking a visit to Chicago, you should be ready to travel more. You didn’t get that. Let me make it easy for you.

You will surely love the architectural designs in Chicago. The city is known for having the most extensive and tallest buildings in the world. This was after Chicago was destroyed by fire. The skyscraper originated from Chicago.

Some of the best iconic examples of the Chicago architecture include:

  • Wrigley building
  • Rookery building
  • The MART
  • Marina city
  • Tribune tower
  • Marina city

The above are just but a few of the iconic architectural designs in Chicago. They provide beautiful sceneries, especially for first-time travelers. You should be sure to enjoy your travel to Chicago.

You may be left staring at these architectures in the middle of a city if you are unaware of their existence. It is good to know what to expect before traveling to Chicago alone.

Some of these buildings may make you want to extend your days in Chicago. They are beautiful for the eye. You can’t get away from them.

How will you convince someone that you went to Chicago and saw Marina city? It will be impossible unless you back your claims with proof. Take a photo of it and make it your best memory in Chicago. 

Public Arts and Monuments

Chicago has the best monuments and public art displays. Some donors provide funds for those public arts. Some of the best open paintings available in Chicago are Chagall’s four seasons, the Picasso, cloud gate, crown fountain, agora, and bronze cow, among others.

All of the above arts and monuments serve various purposes. Some of the statues were built in honor of local heroes. Apart from this, they are also some of the best attractions for tourists and first-time travelers like you. We would all love to visit Chicago one day and see some of these beautiful monuments.

Find out if there are restrictions on accessing the places with those public arts and monuments. A small thing like taking a photo of a memorial might lead you in big trouble. Be careful. This is somewhere you are going for the first time. You don’t know their rules and regulations. Humble yourself. Ask for permission, where necessary, before doing anything with the public arts and monuments. Stay out of trouble.

a shiny dome


This is any style or type of cooking involving the recipes, traditions, and practices. It is mostly associated with the culture of a particular place. When traveling to Chicago, be ready for a delicious meal.

Some of the most famous foods in Chicago include deep-dish pizza, steak, Barbecue, Italian food, Chicago hot dog, Malort.

One of the best places to find these types of foods within the city is the west loop. It has the best restaurants and passionate chefs to ensure your meal is prepared just perfectly.  When you go to Chicago, eat what they eat. Drink what they drink. Do not start making special requirements for your meals.

Explore various types of foods found at their restaurants. Get to know the tastes of those foods. You never know some may be more delicious than you ever imagined. Don’t be so quick to judge from the look of your eyes.

Well, you will need enough money so that you get the best services. Be prepared financially.

 Have you ever gone to a place, specifically a restaurant, and you wonder what you will order? Nothing seems familiar on the menu. What do you do in such circumstances? You end up ordering something you can’t even eat.

It is good to familiarize yourself with the types of foods available in the city.

The Chicago Pedway

This doesn’t sound familiar to you, right? Let’s first start by knowing what a pedway is. In simple terms, this is a footway for pedestrians. It is mainly found in urban areas. 

Some of the pedways in Chicago are open only for business hours, while others are available 24/7. Be sure of the type of pedway to use while in Chicago. 

Also, the Chicago pedway has various entry and exit points. Some of them include One North Dearborn Street, One North State Street, Two First National Plaza, 25 East Washington Street, and 2 North Riverside Plaza. The entry and exit points are very many. Make sure to familiarize yourself with them so that you know where to go and where not to go.

In most cases, the Chicago pedways connect hotels, retails stores, skyscrapers, and train stations around the CBD.

 The pedways are mostly useful during seasons of inclement weather. Inclement weather, for those who don’t know what it means, is a period or season of unpleasant cold or wet weather. 

Since Chicago is one of the cities majorly affected by the winter seasons, the pedways are of significant importance to the residents as well as travelers.

The pedway is an underground network of tunnels built so that you won’t be affected that much by inclement weather.

Pedways makes it possible to go out on the streets of Chicago without having to brave the elements.  Don’t postpone your trip to Chicago just because you are afraid of the winter season. Make good use of the pedways while in Chicago. Don’t keep yourself indoors for fear of the inclement weather.

Also, you should be aware that most of the pedways in Chicago are connected to government/commercial buildings. For this reason, there could be some restrictions. You don’t want to find yourself on the wrong side of the law, yet you have just landed in the city.

Music and Comedy

Who doesn’t love comedy? What of music? Chicago is popularly known for blues music. Some of the most common and popular blues artists in Chicago are Willie Dixon and Muddy Waters.

One of the most influential of the Chicago blues music was Mississippi bluesmen. The blues developed from country blues, which was followed by city blues then urban blues.

You must be ready for such music. This is the type of music that will be played in most events. Don’t be shocked when you hear this. It is part of their culture.

Download some blues music on your phone and put on your headphones on your way to Chicago. Get to know the flow of their sweet blues music. Learn some of the lyrics.  Look at their dance styles. Know some of their most influential artists.

While in Chicago, you are likely to attend live music performance. If you are not familiar with the kind of music they play, it will be a waste of your time and money. Some of the city’s best blue’s institutions include green mill which is located in uptown and Kingston mines found at the Lincoln Park.

Chicago blues music significantly influenced early rock music.

Talking of comedy, Chicago has the best improv theaters for holding comedy shows. Located in the neighborhood of Chicago’s Lincoln Park, the iO theater is home to Chicago’s improvisational comedy. It has unlimited shows every night of the week.

Also, the iO theater in Chicago trains one of the best America’s entertainers, which means you can learn comedy in Chicago. What a joy.

dream theater

The above are the things you should be aware of while traveling to Chicago alone. Chicago is a big city. You have to know some, if not all, the above items for you to be safe. The list is endless. The tips above are just the basic ones. You can research other articles of the same to find out more about the city of Chicago. Do not keep on guessing things when there is a lot of information you can acquire about Chicago.

Make your travel experience to Chicago memorable by knowing the above things. You will surely love it.

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