WindyCityPeach Wanders: 10 Things to Know Before Visiting Chicago

Welcome to WindyCityPeach Wanders 🍑 — a series where I’ll share favorite places, local experiences, hidden gems, practical tips, and everyday adventures from around Chicago.

I may be a proud South Georgia girl, but I’ve called Chicago home for nearly 20 years. During that time, I’ve explored iconic landmarks, neighborhood festivals, museums, restaurants, gardens, lakefront trails, and countless corners of the city that don’t always make the typical travel guides. 

I’ve had such an advantage being a tourist in the city while hosting my friends and family when they come and visit. And I’m visiting places to this day! Whether you’re planning your first visit or you’ve lived here for years, I hope this series helps you experience Chicago through the eyes of someone who chose this city, fell in love with it, and still finds new reasons to love it every day.

And where better to begin than with the question I get asked most often?

“I’m coming to Chicago for the first time. What should I know before I visit?”

I Fell in Love with Chicago Before I Fell in Love with My Husband

I visited Chicago for the very first time in July 2005. My then-boyfriend (now husband) invited me to come visit for a few days.

I stayed for about five days, and those five days changed something in me.

When I tell people I fell in love that week, most assume I’m talking about my husband. While we eventually did fall in love and later get married, the truth is that weekend I fell in love with Chicago.

Because my husband is a lifelong Chicagoan, I got the full Chicago experience that weekend. I visited many of the city’s iconic attractions, but I also attended cookouts, family gatherings, and neighborhood hangouts. I experienced Chicago through the eyes of both a tourist and a resident.

Now, more than twenty years later, that love affair with Chicago is still going strong. And that is how I like to look at Chicago. 

Now, let me be clear: I am a very (VERY!) proud South Georgia girl- 229 born and raised!  Chicago is my adopted home and I have a lot of love for it. 

Like many families who came north during the Great Migration, I understand what it means to build a life somewhere new while holding on to the traditions of home. One of the things I love most about Chicago is how many Southern influences are still found throughout the city. Aside from the brutal winters, I never feel too far away from home.

So before I start sharing my favorite places around the city, let’s start with the basics.

Here are 10 things I think every visitor should know before coming to Chicago.

1. Parking Is Expensive

Parking downtown can add up quickly.

Even with parking apps, you’ll want to plan ahead. I highly recommend downloading Spothero and Park Whiz, and Park Chicago before your trip.

Using SpotHero or ParkWhiz often allows you to reserve parking near your destination for a flat fee, which is usually much cheaper than paying hourly garage rates. Park Chicago is needed for street parking and is the way you feed the meter. 

2. You’re Going to Walk… A Lot

Chicago is a walking city.

Between parking costs, public transportation, festivals, and the sheer size of downtown, you’ll likely find yourself walking much more than expected.

Bring comfortable shoes. You’ll thank me later.

Honorable mention: bring a jacket or a coat (depending on the season). 

If it’s summer, bring a jacket and an umbrella. If it’s winter, bring a coat/gloves/hat/boots (warm items). Check the weather before you come. 

3. You Cannot Do Chicago in One Trip

You simply can’t.

I’ve lived here for nearly 20 years, and there are still neighborhoods, restaurants, museums, and attractions I haven’t experienced.

Instead of trying to see everything, choose a handful of priorities and enjoy them.

Chicago will give you plenty of reasons to come back. And it will be different every time. 

4. Not Everyone Goes Downtown All the Time

Visitors often assume everyone who lives in Chicago spends every weekend downtown.

Not necessarily.

Some people work downtown every day. Some only visit a few times a year. Others live in the suburbs and rarely come into the city at all.

If you’re meeting someone, provide an exact location and time. “Meet me downtown” isn’t nearly as specific as you think.

A lot of the places I visit or take people to- are not located downtown. I love taking people to Rainbow Cone- which is on the Southside. 

5. Chicago Is Not As Dangerous As People Make It Seem

Let’s talk about it.

The nickname “Chiraq” is offensive and unnecessary. Please do not use it.

Does Chicago have crime? Yes. Every major city does.

But the overwhelming majority of visitors will never encounter the places they constantly hear about on the news.

Be a thoughtful traveler. Stay aware of your surroundings, keep an eye on your belongings, and respect the communities you’re visiting.

And please don’t visit neighborhoods simply because you’ve heard about them online or in a song. People live there. They’re not tourist attractions.

6. Your Friend Might Not Actually Live in Chicago

This one always makes me laugh.

If their ZIP code doesn’t start with 606, chances are they don’t actually live in Chicago.

They may live nearby.

They may live in Chicagoland. Or not even in Chicagoland. 

That is not Chicago. 

Also to add- if you’re in any city besides Chicago- you’re not in Chicago. 

7. Chicagoans Are Friendly—But Proud

Chicagoans are some of the friendliest people you’ll ever meet.

Many families have Southern roots and you’ll often find people willing to help visitors navigate the city. 

But Chicagoans are also incredibly proud of their city.

Don’t compare Chicago to New York.

Don’t compare Chicago to Atlanta.

Don’t compare Chicago to Los Angeles.

Don’t compare Chicago to D.C. or Philly.

Chicago is Chicago.

And that’s exactly why we love it.

8. Many of Chicago’s Best Attractions Are Free

One of my favorite things about Chicago is that you can experience so much of the city without spending a fortune.

Some of my favorite free attractions include:

• The Lakefront Trail
• Buckingham Fountain
• Cloud Gate (The Bean)
• Millennium Park
• Grant Park
• Museum Campus
• The Chicago Riverwalk
• Michigan Avenue and the Mag Mile 
• The grounds surrounding the Obama Presidential Center
• Pullman Park 
• Hyde Park 
• South Shore 
• Or many of the parks in Chicago

9. All Harold’s Are Not Created Equally

I said what I said.

Chicago natives know exactly what I mean.

The cleaner the location, the less “down home” it tends to taste.

Ask your people about the best Harolds. My personal favorite Harold’s closed but the close second is located here.

10. The Best Part of Chicago Is the People

The architecture is stunning.

The food scene is world-class- I’ll be sharing more posts on my favorite locations.

The lakefront is beautiful.

But the thing that truly makes Chicago special is the people.

Chicago is one of the most culturally diverse cities in America. Every neighborhood has its own personality, traditions, restaurants, and stories.

No matter where you’re from, you’ll probably find a little piece of home somewhere in Chicago.

And that’s one of the reasons I fell in love with this city all those years ago.

What’s Next for WindyCityPeach Wanders?

This is just the beginning.

In future editions of Windy City Peach Wanders, I’ll be sharing some of my favorite restaurants, neighborhoods, museums, festivals, seasonal activities, hidden gems and local experiences from around the city.

So whether you’re planning your first Chicago visit, looking for something new to do or simply curious about life in the Windy City, I hope you’ll come along for the adventure.

Have a favorite Chicago spot I should visit or feature? Drop it in the comments. You might just see it in a future edition of Windy City Peach Wanders. 🍑