Things to Know Before You Go to Chicago: Windy City and Deep-Dish Pizza

Chicago or to many the ‘Windy City,’ blows visitors away with its towering charm and hearty cuisine. Our guide winds you through the essentials of the city’s most vibrant attractions!

Dramatic sunset over the Chicago skyline
Dramatic sunset over the Chicago skyline

Welcome to Chicago, the ‘Windy City’ where skyscrapers kiss the sky and deep-dish pizza rules the culinary scene. If you’re planning to visit the third largest city in the United States, it’s our pleasure to share some must-know things to know before you go to Chicago.

May this guide help you plan a bespoke trip!

Best Time to Visit and Getting Around

Considered as one of the best places for a family vacation, Chicago shines brightest from April to October when the weather is pleasant. The city also hosts numerous festivals and outdoor activities for visitors of all ages between these months. 

Do note that summer is best for exploring the city’s parks and lakefront, while autumn brings beautiful foliage and cooler temperatures for some interesting snapshots. Now if you visit in winter, be prepared for cold weather and potential snow. And as one of the world’s most spectacular Christmas destinations, you can certainly enjoy the charm of its holiday lights and ice skating rinks that truly spread the cheers of the holiday season.

Another important thing to know before you go to Chicago is how you can get around the city without any hassle. For one, Chicago’s public transportation system, including the ‘L’ train and buses, is extensive and user-friendly. And since the ‘L’ train covers most of the city and suburbs, going from one place to another is easier to navigate even without a car. 

But for seamless travel, consider purchasing a Ventra card, which works on all public transit. Taxis and rideshare services like Uber and Lyft are also readily available throughout the city.

With your travel logistics in place, it’s time to dive into one of Chicago’s iconic culinary delights: deep-dish pizza—a must-try for any visitor!

Chicago’s Famous Deep-Dish Pizza

Of course, no visit to Chicago is complete without indulging in its famous deep-dish pizza. Unlike the delicate, thin crust of Neapolitan pizza, this hearty dish features a thick, buttery crust, plenty of cheese, and a generous layer of tomato sauce. 

Lou Malnati’s, Giordano’s, and Pequod’s Pizza are just some of the most popular spots to enjoy this Chicago staple. Each restaurant has its own twist on the classic, so why not try a few and find your favorite? 

Then after satisfying your taste buds with Chicago’s deep-dish pizza, why not explore the iconic sights that shape the city’s skyline and cultural history next.

Must-Visit Attractions

Chicago is undeniably full of iconic sights. 

Being familiar with these architectural wonders is definitely among the top things to know before you go to Chicago: 

Exploring these beloved attractions will give you a taste of Chicago’s vibrant culture. 

Up next, let’s discover some of the neighborhoods that give the city its unique charm.

A couple walking in downtown Chicago
A couple walking in downtown Chicago

Neighborhoods to Explore

As a city with diverse neighborhoods, you might not know where to visit first. 

Here’s where to get started:

  • The Loop: The central business district is home to many of Chicago’s famous buildings, parks, and museums. It’s definitely a great place to start your exploration.
  • River North: Known for its vibrant nightlife, art galleries, and dining options, River North is perfect for those looking to experience Chicago’s modern side.
  • Lincoln Park: This neighborhood offers a more relaxed atmosphere with plenty of green spaces, the Lincoln Park Zoo, and the beautiful lakefront.

After discovering the unique neighborhoods of Chicago, we bet you’ll want to find a cozy place to rest your head at night. 

With that, let’s explore some accommodation options that cater to every taste and budget.

Where to Stay in Chicago

Deciding on where to stay is another crucial thing to know before you go to Chicago. 

Here are two insights that can help: 

Now that you’ve got your itinerary and accommodation sorted, you’re all set to explore like a true Windy City wanderer!

Ride the ‘Windy City’ Wave with ThisCityKnows

From towering skyscrapers and bustling streets to the savory delight of deep-dish pizza, Chicago truly has something for everyone. With this guide on the ‘Things to Know Before You Go to Chicago,’ you’re all set to discover the magic of this iconic city! 

Plan your adventure with ThisCityKnows, and let Chicago’s charm blow you away! 

And if you have your own insights, tips, or experiences about Chicago, please do share them in the comments section below!

Author: Lei

Armed with curiosity and a knack for planning, Lei loves finding cool stuff to do and places to see that aren't packed with tourists. This City Knows becomes her platform to guide you through the world's wonders, sharing easy tips for making your trip awesome and packed with memories.

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