Chicago Travel Guide

chicago travel guide

Chicago is the largest city in Illinois, the most populous city in the Midwest, and one of the biggest cities in the United States. That’s not all; this world-class city is said to have inspired sky-scraping, multi-story city construction, worked on modern-day sewage systems, and even succeeded in reversing the flow of the Chicago River during Chicago’s developing stage. It’s famous for its skyline, deep-dish pizza, public transport system, industries, public parks, historical high-rises, diversity, museums, and a large number of events & activities! Read on for a complete Chicago travel guide


history of chicago

Pre-18th century, the area that is now Chicago was native American territory. And if you look into the native American history of the area, you’ll see that Miami, Sauk, Fox, & the Potawatomi people have all been inhabitants of the region. 

It was in the late 18th century that Jean Baptiste Point du Sable came to the area, and he is believed to be the first non-native person to settle here. This explorer of African & French descent is referred to as the Founder of Chicago. 

In the years that followed, a settlement developed at the mouth of the Chicago River. It attracted migrants from all over the world and grew larger and became one of the fastest developing cities in the world after it officially became a city in 1837. This went on until the Great Chicago Fire in 1871. This city then went on to rebuild and revolutionize urban living. It is also believed to have spearheaded the era of superstructures.

What to see and do

what to see & do chicago travel guide

Many cities around the world might have taken inspiration from Chicago and adopted its methods of erecting tall buildings. However, Chicago is still among the largest cities by area and has one of the most dramatic skylines. The skyscrapers of Chicago attract a lot of tourists and there are different ways of seeing these structures. You can do an architecture-themed tour on the Chicago River, or get into the waters of Lake Michigan for sweeping views of the big city to its southwest. You could also visit John Hancock Tower or Willis Tower to see the city from the top. Helicopter tours are just another way to see it all!

Chicago is a city that’s filled with things to see, from its skyscrapers to its sandy beaches on the shores of Lake Michigan. There are some waterfront public parks like Lincoln Park, Grant Park (which is referred to as Chicago’s Front Yard), & Millennium Park, which lies in its northwestern corner. Within these parks are smaller attractions like the free Lincoln Park Zoo, Cloud Gate, Lurie Garden & Crown Fountain, Buckingham Fountain, Art Institute of Chicago, & Museum Campus.

For museum lovers, there’s also Fields Natural History Museum, National Museum of Mexican Art, History Museum, Chicago Theater, and even an International Museum of Surgical Science, to name a few. 

Architectural tours & boat tours are a must, & so is a walking tour along the Chicago River & a Crime Tour of the city. Other things to do include sampling the food that is special to Chicago & shopping at North Michigan Avenue.

For more ideas on what to do that aren’t included in this Chicago travel guide, check out my post: Top 10 Things to do in Chicago.


food chicago

The Deep Dish Pizza that Chicago is famous for is what might first come to mind when you think of local food. Some of the best places to go for these cheesy delights are Pequods, Giordano’s, & Lou Malnati’s.

Pizza is not the only thing that is special to Chicago, though! Other delicacies to indulge in while you’re here are Stuffed Pan Pizzas, Chicago-style hot dogs, Italian Beef Sandwiches, & Polish Sausages.

With Chicago being home to ethnicities from all over the world, you’ll find Italian, Mediterranean, Mexican & Latin American, Asian, & Southern Comfort food to treat your taste buds with. 

Yet another way to experience Chicago’s food scene is to take a food-related tour like a Donut Walking Tour, a Pizza Tour, an Odyssey Brunch on the Chicago River, or Spirit of Chicago Dinner Cruise. You could even eat your way through the Time Out Market in Chicago. 

For specific restaurants to visit that aren’t included in this Chicago travel guide, check out my post: Best Restaurants in Chicago.


shopping chicago

State Street in the downtown area is filled with places to visit for shoppers. Across the river and north of the street lies The Magnificent Mile around North Michigan Avenue where you’ll find high-end brands, boutiques, & restaurants. 

Other places to shop or window shop would be Lincoln Square, Andersonville, Wicker Park, & Belmont Avenue. 

If you’re up to going a bit out of the downtown area, northwest of it is Fashion Outlets of Chicago where you’ll find all your household names as far as clothes & shoes are concerned, and several luxury brands too!


geography chicago

Illinois’ largest and most happening city lies in the northeastern part of the state, on the southwestern shore of Lake Michigan. Passing through the city is the Chicago River, which helps connect the Great Lakes area with the Mississippi River. 

Chicago is around an hour’s drive south of Illinois’ border with Wisconsin, and just thirty minutes away from the Indiana Stateline southeast of it. 


accommodation chicago

With Chicago being a big city that sees a lot of leisure travelers as well as business travelers, almost all the well-known hotel chains have a presence here. So do several high-end & boutique properties. If you’re looking for budget options, you’ll find a few hostels around town. 

If it’s your first time in the city and you’re looking at exploring ‘The Second City,’ you might want to stay in the downtown area or just outside it. If you’re here to shop and hang out, you might want to consider a hotel or Airbnb near Magnificent Mile. 

If you’re going to be using public transport, it would be a good idea to take note of where the bus stops & the L Stations are and plan accordingly.


transportation chicago travel guide

A must for this Chicago travel guide: how to get there! For those taking a flight to Chicago, the nearest airports are Midway International Airport & the busier O’Hare International Airport where all the bigger carriers, both national & international, fly into. From the airports, you could take public transport or a taxi into town. 

If you’re traveling from another part of the country, you might also want to check out the option of trains to the city. Chicago is well connected by Amtrak.

Driving into the Chicago Metropolitan Area should also not be difficult thanks to the network of highways around here. There are ‘Expressways’ coming in from the north, northwest, west, southwest, & south. 

Once in the city, you can find your way around using the public transport system — the city’s Ls (elevated rails), or the buses operated by CTA (Chicago Transit Authority). They are quite efficient & user-friendly, too; you just need to get familiar with the card system (Ventra) used here, as well as the colors of the routes that you want to travel to.

If you’re exploring the downtown area, you can do a good part of it on foot. And there are the tours around town too.

Best time to visit

best time to visit chicago

Chicago’s winters can be cold & harsh and it’s summers are quite hot. It’s in the spring & fall that Chicago enjoys pleasant weather. As such, the best time to visit Chicago might be in the months of March, April, May, September, & October. As this is shoulder season, room rates will also be reasonable. And you avoid the summer crowds too! 

Chicago gets most of its tourists in the summer. A lot of events & festivals take place around this time of the year. That’s also when you can watch the firework from Navy Pier. 

However, the city does have events taking place all through the year. Visit around St. Patrick’s Day and you get to watch some parades & other celebrations. You’ll  also witness the dyeing of the Chicago River when the water is turned green! In September there’s the Hyde Park Summer Festival & Jazz Festival. And October brings with it a couple of Wine Fests.

Nearby Destinations

Despite this being a Chicago travel guide, I wanted to include some of the nearby locations that you might want to check out! If you’d like to explore further out, you can go see the capital city — Springfield, or Peoria. You could also visit Historic Galena, or Starved Rock State Park. 

From Chicago, it is also easy to cross some state borders and go into Wisconsin & Indiana.