First Time in Chicago? Here’s Your Guide to the City

First Time in Chicago? Here’s Your Guide to the City

Chicago is known for a lot of things. It’s the windy city, it’s the city of deep dish pizza, and it’s the heart of the midwest. These are only a few of the things that Chicago is known for all across the nation, and even worldwide, and why so many people come to visit Chicago on an annual basis. However, being a city made up of over 3 million residents, Chicago is also one of the largest cities in the United States, and a true metropolis.

As such, the windy city can be a little bit daunting to navigate for a first time visitor, despite the friendly demeanor of the midwest people. Driving into the city, you’ll be greeted by one of the most beautiful city skylines in the world, and it will be hard to miss the billboards in Chicago, but they’re all a part of the experience. Depending on where you’re spending the majority of your trip, from here you’ll likely take a cruise on lake shore drive and end up in one of Chicago’s many neighborhoods, or perhaps even in the heart of the city, downtown in the Loop.

If you’re visiting Chicago for the first time, here’s a relatively complete guide to make the visit well worthwhile.

The Loop and Michigan Ave

First things first, the loop and Michigan avenue are often what people think about immediately when they think about Chicago. Michigan Avenue is home to a slew of high end shops, clothing stores, boutiques, and of course, high-rise buildings. This is where many tourists go to get the true “downtown Chicago ” feeling, get some shopping done, and maybe even try garrett’s popcorn (which is an absolute must).

Michigan and Wacker is just as famous an intersection as any in the United States, and is also featured in a variety of films as sort of the central intersection of downtown Chicago.

Surrounding Michigan and Wacker is the area known as the Loop. The Loop is also a reference to the L which is the elevated train that takes people all throughout Chicago. How the two are related is because the Loop specifically refers to the section of the elevated train that runs in a circle around what is essentially its center. Hence the Loop.

Using the L

Speaking of the L, this is certainly worth discussing for a first time visitor. The L, as mentioned above, stands for the elevated train. This is a tiny bit of a misnomer because the L is also a subway that has underground stations, but a large majority of the train and its stations sit elevated above ground.

The L is color coded, and each color is a different line of the train. In other words, it services a specific section of the city neighborhoods, before it merges with the other lines in, you guessed it, the Loop.

For example, the red line is the line of the train that mainly goes North up all the way until you have to switch to the purple line which takes you up to the most northern neighborhoods of Chicago that there are. The brown line, on the other hand, still travels north, but will also take you west through some quieter less populated neighborhoods.

Understanding the L is integral to navigating the neighborhoods of Chicago.


The Cubs and the White Sox are the two baseball teams of Chicago, and the rivalry is fierce. The Cubs are on the Northside and play at Wrigley Field which is in a neighborhood with the same namesake, Wrigleyville.

The reason Wrigleyville is specifically on this list is because of the revitalization it went through after the Chicago Cubs won the pennant in 2016. This victory not only ended a 108 year old curse, but it also brought a whole new life to the landscape of Wrigleyville and the bar scene there.

If you want to catch a Cubs game, or get some drinking done, you should definitely make time for a trip up to Wrigleyville.

The Pizza

This was already mentioned a bit earlier, but Chicago is the home to deep dish pizza that goes above and beyond all the rest. If you’re not a fan of deep dish pizza, you should still try at least a slice from Pequods, which is one of the best pizza parlors in all of Chicago, Illinois. Their cast iron skillet pizza is absolutely perfect.

A New Experience in Every Neighborhood

Chicago is a wonderful city that is brimming with new experiences waiting to be had. One of the best things about Chicago is the fact that while it’s a big metropolitan area, it truly is made up of small neighborhoods, each with their own distinct atmosphere, feel, and vibe about them.

If it’s your first visit to Chicago, I doubt it will be your last.