How to NOT Look Like a Tourist in Chicago, USA | The Invisible Tourist

“She is novelty; for she is never the Chicago you saw when you passed through the last time.” ~ Mark Twain.

Ever wondered what the secret is to having the most enjoyable trip possible? Welcome to my “Be Invisible” series – your ultimate guide for how to avoid looking like a tourist on your next adventure and guaranteed to boost your entire travel experience.

Bursting with helpful tips and tricks, I’ve asked locals from particular cities around the world to share their insider knowledge on the best ways travellers can become “invisible” when visiting their city and enjoy it like a local. If you’re ready to challenge travel stereotypes, overcome language barriers and embrace what I like to call invisible tourism, you’ve come to the right place!

This post contains affiliate links, at no extra cost to you, I may earn a small commission if you click through and make a purchase. 

Chicago Travel Tips: Do's and Don'ts to Not Look Like a Tourist | The Invisible Tourist
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8 Useful Chicago travel tips to not look like a tourist

Chicago is a city built for tourists. From its museums, restaurants and nightlife to its pedestrian-friendly layout, it has everything a visitor to the US could want. It’s been rated as the third most popular tourist destination city in the US.

Usually, tourism is also a significant driver of the city’s economic engine: nearly 150,000 people are employed in roles related to tourism in Chicago, and tourists add nearly a billion dollars to the city’s economy each year.

It’s easy to see that Chicagoans love tourists, with one significant caveat: we don’t really love tourists that… you know… act like tourists. If you’re visiting our fair city, you’ll have a much better trip if you follow some simple do’s and don’ts to blend in with the locals:

Do try Chicago Style pizza

Chicago Style (deep dish) pizza is the best in the world. Full stop. End of story. If you really want to annoy a local, tell them how you like another city’s pizza just as well or better than ours. Even worse – tell a local that you like New York style pizza better, and you’ll probably get shown the door. Or at least get the cold shoulder.

If you come to Chicago to sample the pizza, try Pizzeria Uno, Lou Malnati’s or Gino’s East restaurants. They’re all great places to enjoy the finest pizza on earth.

Don’t ever put ketchup on your hotdog

Just don’t do it. A Chicago-style hotdog has lots of tasty toppings, but you eat it the way its served. No substitutions. And whatever you do, do NOT order it with ketchup on top. You will get laughed out of whatever restaurant you’re in. You want ketchup on a hotdog, go to California.

Do take the Architecture River cruise

How to get around in Chicago? When the weather is favourable, Chicago’s Architecture Foundation offers a fantastic river cruise to show and teach you about the city’s wide variety of architectural styles. Chicago has many award-winning buildings that span many generations of architectural styles. Learning about the buildings and how they were constructed will help you appreciate the amazing designs and landmarks we have to offer.

Sunset on the Chicago River from London House
Sunset on the Chicago River from London House


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Don’t mess up the names of landmarks

Chicagoans tend to be very persnickety about the names of famous buildings and landmarks around the city. Nothing screams “I’m a tourist!” like calling a place by the wrong name.

Many of the buildings and landmarks had their naming rights sold in the late 20th or early 21st century, but that doesn’t matter…Chicago is a city of tradition, and we stick with the traditional names. Some examples:

  • While the tallest building in Chicago is officially known as the Willis Tower, true Chicagoans will always refer to it by its original name: the Sears Tower.
  • The Chicago White Sox play at a stadium called “Guaranteed Rate Field,” but it is known to true fans as Comiskey Park.
  • The place where the Chicago Bears play? It’s Soldier Field, not “Soldier’s Field.”

Do embrace the sports culture

Chicagoans love their sports teams. Small talk about sports is generally the preferred – and least offensive – way to start a conversation with a Chicagoan. Most residents have deep loyalties to their teams, so don’t compare your city’s team to Chicago’s… even if they’re better.

Don’t argue about baseball or softball

One of the most crucial Chicago travel tips is when it comes to sports, Chicagoans love to argue about two things: which of our baseball teams is better, and what constitutes “real” softball.

White Sox and Cubs fans usually grow up in families that have embraced “their team” for generations. While a small minority of Chicagoans can root for either team, most pick team to love, and one team to hate. If you get pulled into an argument about who is best, it’s likely you’ll end up on the losing side.

Chicagoans also fight about whether softball should be played with a 12” or a 16” ball. To the rest of the world it doesn’t really seem to make that much of a difference – but those who play in this city are passionate about how their style of playing softball is the only “real” kind there is.

Do stroll along the Riverwalk

The Riverwalk is arguably one of the best ways to tour the Loop area. It’s a 1.25 mile pathway that follows the Chicago River from Lake Shore Drive to Franklin Street. During the spring, summer and fall, the Riverwalk is dotted with restaurants and bars where you can enjoy a great meal in a beautiful and unique setting. At various strategic points along the Walk, you can also take staircases or ramps up to Wacker Drive street level to explore nearby areas.

Don’t visit Navy Pier

While Navy Pier is one of Chicago’s more popular tourist destinations, it’s typically only a place that tourists go. It’s been converted from a beautiful example of mid-century architecture into a homogenized tourist mall with overpriced, stale food and souvenir shops. Seriously… just skip it.

Chicago is a great city with everything you’d want to see or experience on a trip. As long as you follow these few simple tips for visiting Chicago, you’ll have a great time and will blend in like a local!



Chicago Travel Tips: Do's and Don'ts to Not Look Like a Tourist | The Invisible Tourist

Ready to be invisible in Chicago?

Now you’ve discovered the best secrets for how to avoid looking like a tourist in Chicago, perhaps you’re ready to make the trip! Why not compare hotel prices here? 

If you’d like to learn learn my strategies for how to not look like a tourist ANYWHERE, take a look at my  book – it was a #1 Amazon New Release!

Do you have any extra tips to add to this list? Let me know in the comments below!
I hope you enjoyed this instalment of my Be Invisible series! If you found this helpful, please share it or follow me on Facebook, Pinterest or Instagram and TikTok for more!

Until next time, 

The Invisible Tourist

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