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Chicago is a city full of history, culture, and entertainment. From the iconic skyline to its world-class art and cuisine, it's no wonder why so many people visit this vibrant city every year. So, whether you're looking for a weekend getaway or a more extended stay, this Chicago travel guide is here to help you make the most of your trip to the Windy City. We'll cover the best attractions, activities, food, and areas for your stay and tips for getting around and staying safe. So, let's get started!

History 

In the middle of the 18th century, Chicago was inhabited mainly by Potawatomis. Jean Baptiste Pointe du Sable founded Chicago's first trading post in 1770. But, it wasn't until 1816 that Chicago became part of the United States under the Treaty of St. Louis. Chicago became a city in March 1837. Besides, it was the fastest-growing city in the world within its first century. In just 40 years, the population grew from over 30,000 to approximately 1 million. 

Chicago was made famous in the 1920s when it became a hub for gangsters. This was also the time of Prohibition and the Great Migration. Moreover, by the 1960s, Chicago was hosting the turbulent 1968 Democratic National Convention. There were also large-scale riots on the streets. Chicago was also famous for its Sears Tower, the world's tallest structure. It became a popular tourist and movie location in the 1970s.

Chicago grew to be a more livable and greener city in the 1980s. However, in the 1990s, the town underwent a major revitalization, with significant investments in infrastructure, the revival of downtown theaters, and improvements to the riverfront and lakefront cityscapes. These developments significantly contributed to Chicago's popularity as a top-rated tourist destination.

Best Time to Visit 

Chicago might have cold winters, but the Windy City has warm and sunny days with live music, blue skies, and community festivals. When the city's beaches are at their best, June to September is the best time to visit Chicago. Besides, runners might want to delay seeing it until October, when Chicago hosts its annual Chicago marathon. The Chicago Blues Festival is June's highlight, while the Taste of Chicago outdoor food festival allows you to sample a variety of local favorites. 

The Christkindlmarket is for those brave enough to stand up to the freezing temperatures. But it offers the opportunity to get on your skates through Grant Park. There are also many opportunities to see Christmas lights at Navy Pier and Lincoln Park Zoo.

Things to Do & Places to See  

Here are the top things to do and places to visit in Chicago.

Grant Park and Buckingham Fountain 

Grant Park is a 313-acre expanse of green space. It starts at the east edge of the Loop and ends at the northern fringes of Chicago's Near South Side. It is recommended that first-time visitors spend a lot of time in Grant Park. This park contains many of Chicago's most famous attractions. These include The Field Museum, Shedd Aquarium, and the Art Institute of Chicago. Millennium Park is also on the northwest corner of Grant Park. There are also baseball diamonds, flower gardens, and walking paths.

Furthermore, Buckingham Fountain is in the heart of Grant Park. This tiered fountain is the largest in the world and features 133 water jets. Besides, they shoot water up to 150 feet high during choreographed 20-minute displays. The shows take place from 8 am to 11 pm, depending on the weather. The fountain's last performance of the night starts at 10:35 pm.

Art Institute of Chicago 

The Art Institute of Chicago is home to nearly 300,000 pieces from around the globe. It houses one of the country's most important collections of post-impressionist and impressionist art. There are also pieces from the Byzantine period.

The Art Institute also has a variety of interesting artifacts. These include European armor and the Thorne Miniature Rooms. These rooms showcase interior design and furniture in Europe and America between the 13th and the early 20th century. The Art Institute also hosts traveling exhibitions covering various topics and showcasing diverse artists and genres.

Moreover, recent visitors have given high marks to the Art Institute of Chicago due to its outstanding collection. The museum's Impressionist collection features works by famous artists such as Renoir, Monet, and Van Gogh. 

Cloud Gate 

Cloud Gate, a stunning piece of art that is undoubtedly one of Chicago's most popular spots to visit, is an iconic landmark. This is the ideal spot to take a selfie. Since its inception, it has been a favorite among tourists all over the globe. This fun installation, also known as the Beanbag, is a house made of mirrors that's a must-see for anyone visiting Millennium Park.

Navy Pier 

Navy Pier extends out onto Lake Michigan and offers plenty of family-friendly entertainment. First, you'll see the Ferris wheel, which stands 196 feet tall. You will notice it first when you step onto the pier. There's also a drop tower as well as a carousel. After the thrill rides, the children can take a cruise on the Chicago River. Or, they can spend time exploring the Chicago Children's Museum.

Besides, Navy Pier is open to all ages. You can shop at various shops or have a beer at the Navy Pier Beer Garden. There are also many concerts here. On Wednesdays and Saturdays, impressive fireworks display light up downtown. Furthermore, many of the city's most famous operators offer Segway tours that take you to the pier on the summer evenings.

John Hancock Observatory 

Also known as 360 Chicago, the John Hancock Observatory is the most famous structure. It offers a panoramic view of Chicago. This is an incredible sight that you should not miss. You will have an unforgettable experience. This is also Chicago's most loved place. You can see five states and Lake Michigan from this location.

Lincoln Park Zoo 

This zoo is 2 miles north of Loop in Lincoln Park's North Side neighborhood. It is home to almost 200 species, such as sloths, zebras, and hippos. The zoo's furry and scaly friends can be viewed in their natural habitats. Also, visit the Regenstein Center for African Apes to see gorillas. Or visit the Kovler Seal Pool, where you can get up close to harbor seals. Besides, daily feedings and training of seals take place at 11:30 am. However, you may need public transport or a taxi to reach the zoo. There is limited parking in the lot.

Culture & Customs

Chicago is home to many fine restaurants. But don't overlook the chance to try some local cuisine. For example, Chicagoans believe their hot dogs and pizza are better than those from New York City. Also, remember that soda in Chicago is known as "pop."

Chicagoans are also passionate about their sports teams. So it shouldn't be challenging to find a fellow Chicagoan fan of "da Bears" or "da Cubs" at any sports bars throughout Wrigleyville.

Moreover, the Reader and Time Out Chicago have information about musical and theatrical performances available throughout the city. And don't miss out on one of Chicago's most famous comedy shows. These are presented regularly by local comedy clubs like UP Comedy Club.

What to Eat 

Chicago cuisine is often associated with three things: hot dogs, steak, and pizza. However, Windy City is constantly at odds with New York City about who can make the best slice. While New Yorkers like pizzas wide and flat, Chicagoans prefer deep-crust pizzas that can hold many toppings.

Chicago is also famous for its steakhouses. The Loop and North Side have many fine restaurants offering prime beef cuts. Joe's Seafood is one of Chicago's most renowned steakhouses. You will find them just off The Magnificent Mile and Bavette's Bar & Boeuf, in the area of River North.

The Italian beef sandwich is another popular food choice. This seasoned roast beef sandwich was created by Chicago's Italian immigrants in the early 1900s. You will find it in many hot dog stands and restaurants. Portillo's is a great place to get a traditional Italian beef sandwich. There are two locations downtown: one is on West Ontario Street, and the other is on West Taylor Street.

Where to Stay 

Chicago offers many great places to stay. Here are some of the most desirable areas. In addition, the city provides a broader range of Boutique hotels with marble bathrooms and a fitness center.

The Loop (Downtown Chicago)

This district has all the major attractions within walking distance. It is also home to some of America's oldest skyscrapers and modern steel and glass giants like the Willis Tower, the third-largest US building. Besides, the adjacent Millennium Park and Grant Park offer pleasant, green escapes along Lake Michigan. Also, Chicago River boat trips provide the best views of the city. The Loop is the central point of the city's public transportation network. It makes it easy to get anywhere in the city from the Loop. 

South Loop and Lakeshore East (New Eastside)

The South Loop and Lake Shore East are famous for families because they offer easy access to Chicago's top kid-friendly attractions. They also have excellent hotels and a more peaceful vibe than the main Loop. You will find South Loop near Shedd Aquarium and the Field Museum of Natural History. Lakeshore East is on the Chicago Riverwalk. 

River North 

River North is a neighborhood just north of the Loop and Chicago River. It's one of Chicago's most lively neighborhoods. You can find top restaurants and bars here. There are also some of the city's most famous clubs and bars. Three Dots and a Dash offers a classic tiki bar atmosphere, while Bassment has live music. Moreover, TAO Chicago is an Asian-themed restaurant that has transformed into a trendy nightclub.

The Kerryman has the best Guinness. House of Blues Chicago is also available. It is just a half-hour walk or a train ride from River North to Old Town, a nightlife center that also hosts The Second City, a renowned comedy club.

Magnificent Mile 

The Magnificent Mile is the ideal place to stay in Chicago if you love luxury shopping. High-end stores like Water Tower Place and other shops are only available in Chicago.

The sheer size and beauty of the buildings will also strike you as you drive up North Michigan Avenue for Magnificent Mile. The Tribune Tower, Wrigley Building, Chicago Water Tower, and John Hancock Center are all breathtakingly impressive.

Lincoln Park 

Chicago's most significant green space is approximately two miles north of the Loop. Its name reflects the neighborhood of stately townhouses and leafy streets that surround it. It is a safe and laid-back area that's great for families. Lincoln Park, which includes the Peggy Notebaert Nature Museum and many monuments, is the main attraction. However, many high-end shops and restaurants along North Clark Street exist. The Chicago History Museum and a few family-friendly beaches on Lake Michigan.

How to get around 

Chicago is very walkable. It also has a great public transit system, which includes buses and trains. Besides, Uber, Lyft, and taxis are all available in some parts of Chicago.

The train system, known as "El," is elevated above the ground and runs through most of the city. The El makes it easy to travel from Chicago Midway and Chicago O'Hare to downtown Chicago.

Chicago has a lot to offer in terms of train service. But, if you learn how to use buses, there are very few places you won't be able to reach by public transit. You can also access bus information via text. In addition, taxis are easily found downtown and in the surrounding areas. 

How to Stay Secure 

Exercise caution while out and about, just like you would in a big city. Always keep your valuables close at hand. When you travel after dark, ensure you have a good idea of where you are going, and don't walk alone. Also, avoid the West and South sides of neighborhoods. These areas are more prone to gun violence. For example, the White Sox stadium is on the South Side. Visitors who wish to attend games should use the L, which stops outside the stadium. Furthermore, although areas such as Kenwood and Hyde Park are less affected than that west of Lake Michigan, it is still important to be alert.