Chicago

Chicago—a cosmopolitan and commercial metropolis—is one of the largest and most important cities in the United States. It is home to stunning architecture, the Chicago Bean, and the the delicious deep-dish pizza.

Overview Attractions / Activities Adventurous Activities Food Final Comments

Nicknamed the Windy City, Chicago is an international hub of commerce, culture, finance, and technology, among others. Being one of the largest cities in the United States, it also features a diverse selection of attractions and food.

Either for work or for fun, I often find myself back in the Windy City. From 2019 to 2020, I flew into Chicago no fewer than 10 times. It is a vibrant and fun city with entertainment options that will please all visitors.

When you visit, make sure to follow this adventure guide to maximize your time in Chicago.

Recommended Duration of Visit

3 days (ideal), 2 days (doable), 1 day (difficult)

Click for some interesting facts about Chicago

As of 2020, Chicago is the third-largest city in the United States.
The McDonald’s and Boeing headquarters are in Chicago.
Walt Disney was born in Chicago (in the Hermosa section of Chicago).
Hugh Hefner, the creator of Playboy magazine, was born in Chicago.
Acclaimed actors such as Harrison Ford and Robin Williams were born in Chicago.
Barack Obama and Oprah Winfrey were Chicago residents.
Michael Jordan, although born in New York, is often associated with Chicago since he played for the Bulls.
Many comedy icons such as Bill Murray, Tina Fey, and Seth Meyers got their start in Chicago.

Before You Go

Flights / Getting There: Flying directly into Chicago is the most efficient strategy.

Overview

Climate: Chicago’s climate intuitively follows the normal pattern of North America. There is one distinction: winters (December, January, February) are very cold. The Great Lakes often contribute to brutal winters. Summers (June, July, August), on the other hand, are very pleasant.

Communication: English is the official language.

Navigation: Traveling by car is, by far, the best way to explore most of what Chicago has to offer.

Lodging: Lodging, in general, is moderately expensive in a metropolis such as Chicago. When possible, staying within the outskirts of the city is ideal. I often stay in the Oak Park region (west of Chicago) and drive into the city.

Activities Planning: Most attractions are free to visit, but they are far enough apart to necessitate driving.

Special Considerations

Parking is relatively pricey in the Chicago downtown area. Therefore, it would be ideal to plan a whole day for exploration. It’s often very expensive to park for short durations. Grant Park North or South are decent options for parking. Both garages are in a relatively central area in downtown Chicago.

General: Winters are especially brutal in Chicago, but the weather is relatively cold mid-Fall as well. Make sure to bring plenty of cold gear for visits planned during the Fall or Winter.

Peak Seasons: Summer is the ideal and peak season because Chicago has nearly perfect weather in the summer. Early Fall attracts a fair amount of visitors as well.

Currency: United States Dollars (USD). Currency Converter.

Things to Do: Attractions and Activities

Most of the time, attractions are paired up based on similarity and/or proximity. All the names provided are easily searchable on Google Maps.

Berlin Wall Monument: From 1961 to 1989, the Berlin Wall represented the physical and ideological Cold War divisions in Berlin.

This piece of the wall was donated by the city of Berlin to the citizens of Chicago as “an expression of gratitude for the invaluable assistance rendered by the United States of America in securing the safety and freedom of Berlin, in bringing down the wall, and in supporting the reunification of Germany and Berlin.”

For some reason, this section of the Berlin Wall can be found in the Western Metro Station. Other random monuments or art pieces can be found throughout Chicago. Prepare to be thoroughly amused as you explore Chicago because something random and interesting could be around any corner.

For more interesting information on the Berlin Wall (or Berlin in general), refer to the Berlin Adventure Guide.

Cost: Free to visit. Recommended Duration of Visit: 10 – 15 minutes.

Chicago Riverwalk: Flanking the Chicago River on both sides, this waterfront offers views, dining, piers, bridges, boats, and lights. Arguably, the riverwalk is the best way to explore the city and admire its stunning architecture.

Cost: Free to Visit. Recommended Duration of Visit: 1 – 2 hours.

This is the definition of a hidden gem (hidden wall?). It is quite far north of Chicago, in a random location, and distant from other major attractions.

As someone who has visited in the morning and at night, I recommend a stroll during nighttime. You can also partake in the boat tours that run up and down the river (not available at night).

Buckingham Fountain: Won from Buckingham Palace in London via a poker game, this Chicago landmark is one of the largest fountains in the world.

Okay, I was just kidding about the poker game thing. But what I’m not kidding about is the fact that the fountain is modeled after a cake (rococo-style) and inspired by the Latona Fountain at the Palace of Versailles.

The fountain represents Lake Michigan, and the seahorses at the corners represent the four states bordering the lake (Wisconsin, Illinois, Indiana, and Michigan).

Cost: Free to visit. Recommended Duration of Visit: 15 – 30 minutes.

Grant Park: Grant Park, named in honor of President Ulysses S. Grant, is located near Chicago’s downtown and business district. It features gardens, art pieces, and spectacular skyline views, among others.

Cost: Free to visit. Recommended Duration of Visit: 1 – 2 hours.

During the winter (around Christmas time), the fountain is often decorated with Christmas lights. Unfortunately for me, I went during a time when no one gave a damn. They didn’t even turn the damn thing on.

Buckingham Fountain is located within the greater Grant Park region. Lakefront Park is across the street. Hutchinson Field, located within the park, is a giant field for sports activities, picnics, and large events.

Millennium Park: Opened in 2004, Millennium park celebrates the third millennium (spanning 2001 – 3000). As the top tourist destination in the Midwest and one of the top tourist destinations in the United States, it features a variety of public art pieces, gardens, skyline views, and, of course, the famous Cloud Gate, among others.

And since the park sits atop a parking garage (that’s underground), it is technically the world’s largest rooftop garden.

Cost: Free to visit. Recommended Duration of Visit: 1 – 2 hours.

Cloud Gate: Cloud Gate, the centerpiece of Millennium Park, is Chicago’s most recognizable landmark. Its design is meant to reflect and distort the city’s skyline. However, calling it a gate is a bit of a stretch. It’s literally a giant metallic bean, so its nickname is The Bean.

What’s truly special about The Bean is its engineering. This legendary legume was created using 168 precisely-cut steel plates. The plates, after being welded shut, were polished so finely that people often assume the structure was just designed as one massive bean.

Cost: Free to visit. Recommended Duration of Visit: 15 – 60 minutes (depending on the crowds).

Unfortunately, only service animals are allowed in the park. Smoking, bicycling, rollerblading, barbecuing, and drinking alcohol are prohibited. During Christmas time, Millennium park hosts the annual Christmas tree lighting celebration.

Cloud Gate's tourist density is disgusting, disheartening, and downright detestable at times. Therefore, it would be wise to arrive as early as possible during the mornings in order to achieve the desired photo.

Things to Do: Attractions and Activities

Most of the time, attractions are paired up based on similarity and/or proximity. All the names provided are easily searchable on Google Maps.

Berlin Wall Monument: From 1961 to 1989, the Berlin Wall represented the physical and ideological Cold War divisions in Berlin.

For some reason, this piece of the Berlin Wall can be found in the Western Metro Station. Other random monuments or art pieces can be found throughout Chicago. Prepare to be thoroughly amused as you explore Chicago because something random and interesting could be around any corner.