Chicago

The Best Chicago Neighborhood Walking Tours | Sherpa Tours

Table of Contents

Chicago neighborhood walking tours are one of the best ways to discover the beautiful architecture and history of the Windy City.


There are no two ways around it: Chicago is one of the USA’s greatest cities. From its soaring skyline filled with steely skyscrapers to its fierce love of sports, this is the gem of Midwest America.

Architecture takes center stage here, and even the biggest city-skeptics can appreciate the sheer beauty of Chicago’s skyline. It was here where the skyscraper was invented, and it shows. Concrete, steel, and glass combine in a striking testament to human innovation. As you wander through the city, craning your neck upwards reveals a wealth of treasures waiting to be discovered.

But don’t forget to scour the ground level as well. Creative public art installations lie around every corner, while a dazzling array of world-class galleries are home to some of the best artworks the world has ever known. A Millennium Park tour is a great place to start, where you’ll find famous works such as The Bean and Crown Fountain.

Loosen those belt straps because Chicago is a serious foodie city as well. Locals take their cuisine very seriously, from their classic hot dogs to the iconic deep-dish pizza. Also on offer is a fine range of global eats, from Latin American to kitchens inspired by the deep south. There’s seemingly no end to this destination’s culinary prowess – luckily, our Chicago neighborhood walking tours will help you work it all off before you leave.

Welcome to Chicago.

History of Chicago

Early Beginnings

The Potawatomi people were first to live in the area around Chicago, usurped by settlers who arrived in 1803. The town got off to a slow start – the population was only 340 by 1833. Although soon after, thousands would flock to the town searching for work, as construction on the Illinois and Michigan Canal began, linking the city to the Mississippi River and Atlantic Coast.

A Booming Frontier Town

As America’s great railways began to be built in the 1860s, Chicago became one of the main connections between the established East Coast and the wild frontier to the west. As such, thousands poured into the city from all over, and innovation boomed. The city’s steel industry also profited from the Civil War while propelling the city to new heights.

The Great Fire of Chicago

It all ground to a halt in 1871, when a blazing inferno engulfed the city. Rumor has it that it all began with a cow kicking over a lantern – no one knows for sure, but what’s certain is that much of downtown was destroyed in less than 36 hours. As the city was rebuilt, unique architectural designs came to the forefront. The skyscraper was invented, and the cityscape developed into one of the most famous in the world that we see today.

Sherpa Tours has two Chicago architectural walking tours: One is a Chicago art-deco walking tour, while the other explores Chicago’s most famous architecture.

Chicago Gangsters and Prohibition

Another famous period of Chicago history is during the Prohibition Era (1920–1933), when notorious gangster Al Capone had a firm grip on Chicago’s gambling and liquor trade. But other gangsters also had designs on Chicago; the result was a bloody era of shootouts, sharply dressed gangs, murder, and robberies.

For a more in-depth look at the events that helped shape this city, check out our range of Chicago guided walking tours below. All our offerings are also available as Chicago virtual tours, letting you discover the Windy City from the comfort of home.

Where to Stay in Chicago

The 5 Best Neighborhoods to Stay in Chicago

  • The Loop
  • River North
  • Lincoln Park
  • Streeterville
  • Wicker Park

For many visitors to Chicago, staying in The Loop neighborhood will be the best choice. This is downtown Chicago, the business district where you’ll find towering skyscrapers, architectural wonders, and fantastic public art installations.

For art lovers in Chicago, you’ll do well to stay in River North. This neighborhood is famed for its incredible number of art galleries and museums, making it a great spot for culture lovers. But it’s also sprinkled with some of the city’s best bars, restaurants, and clubs, making it a fantastic location if you enjoy nightlife as well.

Chicago architectural walking tours Riverwalk

The river is also one of the best vantage points to take in the city. Our Chicago Riverwalk tour is the perfect way to enjoy this beautiful part of the city.

Lincoln Park is the perfect choice for budget travelers looking for a more affordable neighborhood. It’s also one of Chicago’s greenest districts, making it a great choice for families as well. Home to the famous Lincoln Park Zoo, this is a calm and residential area, perfect for experiencing local life in Chicago.

Streeterville is a trendy neighborhood nestled between Lake Michigan and the high-end shopping street Magnificent Mile. This is a fantastic spot to stay in Chicago, well connected to both the center and Chicago’s Gold Coast. It’s also the location of Navy Pier, a fun attraction with shops, restaurants, theme park rides, and plenty of games.

For those interested in Chicago’s Magnificent Mile, our walking tour of the area delves into the architecture, history, and development of this famous street.

Finally, Wicker Park is another great all-around choice in Chicago. Loaded with cafés, pubs, and restaurants, you’ll have a great time mixing with the cool kids of Chicago here. There are also several concert venues, letting you easily catch a live gig while you’re in town.

What to Eat in Chicago?

The 5 Must-Try Dishes in Chicago

  • Deep Dish Pizza
  • Chicago-Style Hot Dog
  • Italian Beef Sandwich
  • Sweet Steak
  • Gym Shoe Sandwich

You’ve likely already heard about Chicago’s famous deep-dish pizza. More a tomato and cheese casserole than a pizza in the traditional sense, there’s no denying that this is a delicious treat to enjoy in Chicago. Across the city, you’ll find several must-try restaurants with their own take on this sumptuous dish.

A Chicago-style hot dog is the perfect street food while taking a  chicago neighborhood walking tour

Another greasy fast-food treat is the Chicago-style hot dog. There’s no ketchup allowed on hot dogs here. Instead, this beef hot dog is slathered in yellow mustard, diced white onion, tomato, sweet pickle relish, dill pickle spear, sport peppers, and a dash of celery salt, served in a steamed poppy seed bun.

Another of the region’s most important dishes is the Italian beef sandwich. Originating in the city in the 1930s as a workingman’s lunch with the influx of arrivals, you can find it all over Chicago. The sandwich features shaved roast beef, sweet peppers, giardiniera (a Chicago condiment), and gravy.

The sweet steak is Chicago’s take on America’s famous cheesesteak. This sandwich is filled with bits of rib-eye steak, fried onions, sweet peppers, tomatoes, and cheese, topped off with a tangy sweet sauce.

You’re not full yet, are you? We’ve got another classic Chicago sandwich to get through. The gym shoe sandwich originated in Chicago’s south side and is a half beef half Greek gyro. This delicious and messy treat is loaded with three types of beef, topped with onions, lettuce, tomato, cheese, mayonnaise, tzatziki, and giardiniera.

Insider Information

Capital of Sports

Another fantastic way to experience the real Chicago while you’re in town is to watch a game. Whether you’re watching the Chicago Bulls play basketball or the Chicago Cubs at Wrigley Field, there’s a fiery passion to the local teams here that is incredible to experience. Heading out to show your support is a local rite of passage and an easy way for visitors to catch a glimpse of life in the Windy City.

World-Famous Comedy

Chicago is a city that’s known the world over for its fantastic standup comedy scene. Theaters across the city have acted as the stomping ground of America’s funniest personalities, from Stephen Colbert to Tina Fey to Bill Murray. Catch a live act while you’re in town, and you might just discover the next star. The city’s most popular comedy club is Second City.

Singin’ the Blues

Chicago was introduced to the Blues after the Great Migration, when thousands of black migrants streamed into the city. The Windy City was home to stars such as Bo Diddley, Muddy Waters, Howlin’ Wolf, and Willie Dixon; some of the most famous records were made in this city’s hallowed, musical streets. Checking out a live blues show when you’re in town is a great night out.

The 5 Best Blues Music Clubs in Chicago

  • Buddy Guy’s Legends
  • Kingston Mines
  • The Smoke Daddy
  • Rosa’s Lounge
  • L.U.E.S

Chicago is a fantastic choice for a city break from its stunning architecture to a fierce pride in its cuisine. To discover the Windy City from the ground or the comfort of home, check out our range of Chicago neighborhood walking tours below.