The Ultimate Chicago Travel Guide

If asked to think of aspects that make Chicago great, anyone can immediately think of a few universally known examples. Most would immediately say Chicago is the home of deep dish pizza, the Cubs, the White Sox, the Bulls and the Bears. And they wouldn’t be wrong.

These attractions alone drive people to visit Chicago in droves every year, and the proof is in the numbers. In 2012, over 46 million people visited the Windy City, many of which filled Chicago stadiums and cheered their favorite teams. But you’ll find more than sports and pizza places in Chicago. Much more!

As the third largest metropolitan area in the country, Chicago is a cultural hot spot with a long history and many hidden gems. Anyone can explore the streets of Chicago and discover something new. It’s no surprise that Hollywood superstars who grew up in the city have written public love letters to their hometown. John Hughes based many of his movies in Chicago, including Ferris Bueller’s Day Off and Home Alone. Kanye West dedicated his hit song Homecoming to his home Chi-town, and the band that shares the city’s namesake is still going strong.

This in part is why Chicago is highly recommended as a place for visitors to experience. If you’re in town for the pizza and sports but want to stay for the arts and culture, Chicago has something for you. It is a city that has history, culture and commerce — all of which have helped it become the great place it is to visit and stay today.


Chicago’s History

Chicago was first incorporated as a town in 1833. Before then, it was known as a water transit port and trade center converted from Native American territory. At the time, Chicago was home to the Fort Dearborn army base, built by what now is known as the Chicago River. The base was built long before Chicago was first incorporated in 1803, but was destroyed by a deadly raid during the War of 1812. It was quickly rebuilt by 1816, only four years later. The second Fort Dearborn survived to see the city’s incorporation but was only destroyed again. This time by the Great Chicago Fire in 1871.

The Great Chicago Fire was a devastating event, fueled by a domino effect of bad circumstances. No one knows where it really originated, just that it started in or around a barn and spread quickly. Dry conditions encouraged the flames and high winds carried embers into the city. The buildings then, over two thirds made of wood, fed the fire. And many of the houses had highly flammable shingle or tar roofs.

It was one bad stroke of luck after another, and the fire raged for two days. At the end, it killed hundreds of people and left thousands homeless. It was a horrible tragedy that left survivors in shock. After news got out of the fire, cities, companies and individuals around the country sent donations to Chicago in the aftermath. The donations ranged from money to food and clothing, anything that could help after the devastation. Chicago did what it had done with Fort Dearborn so many years before. It began to rebuild quickly, as it was now a bustling city that housed and employed the over 100,000 people that had been left homeless by the disaster.

It was this drive to succeed that has helped Chicago grow to be the great city that it is today. Instead of letting the devastation of the Chicago Fire define it, Chicago used the disaster to learn and build. The world’s first skyscraper — the Home Insurance Building — was built in Chicago in 1885, only 14 years after the devastation of the Great Chicago Fire. It was a significant symbol of growth and innovation. They knew they had to rebuild and honor what was lost and never really stopped building.

Today, Chicago is a destination hotspot. It is the home to some of the most iconic architecture and public art in the world, a synergy between nature and creativity. With our public concerts, free public events and numerous parks, walking around Chicago alone is a treat for those who come enjoy what this great city has to offer.

Public Sights and Art

Chicago is a vibrant cultural hub that offers visitors and natives alike a wide arrangement of theatres, sights, museums, events and parks to enjoy, many of which are free and open to the public. The gothic-style architecture found in this city, along with many pieces of public art that decorate and complement the space, make walking through the city a truly enjoyable experience. The parks, which bring slivers of tranquility to such a busy area, are sprinkled with creativity as much as greenery. And the museums offer a connection to history that is very much part of what holds the city together.

It is no exaggeration that Chicago has something for everyone. Whether you’re traveling alone or with family, for business or pleasure, Chicago has many things to offer around every corner, street, and even down the river itself.

the-chicago-river1. The Chicago River

The Chicago River is a main character of this city and is constantly bustling with activity. With walkways along each side of the river, visitors can enjoy the sights all the way down to Lake Michigan. Visitors can expect to see the Trump Tower, Marina City and the Wrigley Building all from the Chicago River Walk.

If walking is too slow, visitors can rent bicycles from Chicago’s Divvy Bike service, take a segue tour or join an architecture river tour. The River Walk also serves as a public park and is home to many events. We all know that the Chicago River is dyed green every St. Patrick’s Day and is the place to be on this holiday, but it is active during other times of the year, too. With summer in full swing, for example, seeing kayaking clubs floating along the river is commonplace here.

2. The Municipal Device

If you enjoy finding interesting clues in your surroundings, search for the Municipal Device the next time you visit Chicago. The Municipal Device is a symbol of Chicago civic pride and can be found hidden in the city’s architecture. It’s the letter Y in a circle, symbolizing where the three branches of the Chicago River meet at Wolf Point.

An inverted Y with a vertical stripe on top symbolizes the reversal of the flow of the Chicago River, a massive water canal engineering project completed in 1900. The inversion of the Chicago River was a necessary step to keep the city functioning so that it could exist today. It was a successful project to reverse the flow of the Chicago River away from Lake Michigan to reduce pollution, and it has allowed the city to flourish, as access to clean and safe water is instrumental. If it hadn’t been for the reversal of the Chicago River, Chicago itself might not exist today.

You can have fun searching for it as you take a walking tour the Chicago Loop, Chicago’s business district and the most active area of the city. The Municipal Device is the symbol of Chicago and can be found on many public structures, such as:

  • The Chicago Cultural Center
  • City Hall
  • The Chicago Theater Marquee
  • The Civil Engineering Monument of the Millennium
  • Grant Park
  • The Harold Washington Library Center
  • The LaSalle Street Bridge
  • On the light fixtures in Millennium Park
  • The Rookery Building
  • Navy Pier
  • The River Walk Gateway

These are just a few. There are many other places that are integral to Chicago that feature the symbol. So if you see it, know that it is purposely there to celebrate one of the things that made Chicago possible.

3. The Bean/Cloud Gate

Cloud Gate, also known as The Bean for its shape, is a metal structure inside Millennium Park designed by Anish Kapoor in 2006. Cloud Gate was fashioned to mimic the look of mercury metal and is famous for its polished mirror-like exterior with no visible seams.

Cloud Gate has become a go-to destination for photo opportunities in Chicago and a fun tourist spot in the Chicago Loop district. It reflects the Chicago skyline on its surface and weighs 98 long tons. This piece can expand and contract with the change of temperatures. It sits on two rings which move independently of each other, allowing the piece to move independently itself. It’s interactive with its environment and intelligent by design.

Bobby’s Bike Hike offers a walking and food tour around Chicago which includes a stop at Cloud Gate was well as other famous Chicago landmarks. During the tour, you’ll also get top stop at Giordano’s for a bite to eat. When you are planning your trip to Chicago, be sure to check out Bobby’s Bike Hike for all kinds of Chicago walking and biking tours.

4. The Crown Fountain

Also found in Millennium Park, the Crown Fountain is an interactive sculpture and open pool that offers relief from the summer heat. The fountain is 48 by 232 feet with a water depth of about .25 inches, making it one of the world’s shallowest pools. But it’s the 50-foot towers at each end that really steal the show. Both towers have LED screens with videos of over 960 Chicago area residents that were videotaped for this project. Many who visit the Crown Fountain are residents themselves that come to see their videos, but others come to get a little relief from the summer heat.

5. The Navy Pier

Found along the Lake Michigan shoreline, the Navy Pier is home to many fun rides. The 15-foot Ferris Wheel is based on the first Ferris Wheel that debuted right here in Chicago at the 1893 World’s Columbian Exposition. In addition to the famous Ferris Wheel, you’ll also enjoy a wave swing and a carousel, making it a great place for families to visit.

6. The Lincoln Park Zoo

The Lincoln Park Zoo is free and open to the public. A credited member of the Association of Zoos and Aquariums (AZA), it is one of the oldest zoos in the country and one of the few remaining that offers free admission to visitors. Lincoln Park Zoo is home to many animals such as lions, tigers and bears — about 200 different species in all.

7. North Avenue Beach

A short distance from the Lincoln Park Zoo is North Avenue Beach, a popular summer destination with a west coast vibe. The beach faces Lake Michigan and offers a nice little summery oasis in the city.

zombie-escape8. Zombie Escape

For the visitor who likes exciting and planned activities, you can book a Trapped in a Room With a Zombie adventure with a group of friends for some scary fun. The objective is to find clues that will help you find a way out of the room before the zombie attacks. Participants have 60 minutes to discover the clues in the room and work together to get out safely. It’s a great activity that inspires the detective in all of us.

9. The Willis Tower

What we once knew as the Sears Tower, the Willis Tower is the second tallest building in the United States. It is also home to one of the observations decks open to the public in Chicago, allowing individuals to visit and photograph the city from new heights.

10. The Magnificent Mile

Just like California’s Rodeo Drive and New York’s 5th Avenue, The Magnificent Mile is Chicago’s go-to place for shopping excursions. It’s home to stores such as:

  • Eileen Fisher
  • Brooks Brothers
  • AllSaints
  • Cartier
  • Max Mara
  • Bloomingdale’s
  • Vince
  • Nordstrom
  • Macy’s
  • Neiman Marcus

The Magnificent Mile has something for everyone.

11. The Money Museum

Located at the Federal Bank of Chicago, the Money Museum is also free and open to the public. Inside you will learn not only about historical currency, but also about counterfeit money. At the Federal Reserve exhibit, you will receive gift bags of shredded money that was destroyed after being too worn to be in circulation.

12. Borders

An installation of statues inside Grant Park, Borders is located in the Solti Gardens at Grant Park. It’s a series of human-shaped sculptures sitting and posing along the park. The Borders installation offers a fun photo opportunity for visitors. You can try to mirror the sculptures or pose for your very own wacky pictures. For children or their families, it can be a fun bonding opportunity.

13. The Field Museum

The Field Museum is one of the largest natural history museums in the world and can be found in Chicago. It is also home to Sue, the largest and most complete T-Rex found by archeologists to date. The Field Museums Library holds over 275,000 books.

The Field Museum is also next door to the Shedd Aquarium, a popular attraction for families at all times of the year.

best-chicago-style-pizzaThe Best Chicago Style Pizza

There is denying that Chicago is synonymous with deep dish pizza. A sturdy, full-on meal that has more in common with pies than its east coast sibling, the Chicago deep dish pizza is also a point of pride in this city.

You may be interested in seeing the sights of Chicago now, but if you’re in search of the best Chicago style pizza, that desire won’t go away after seeing the sights. And what better place to enjoy Chicago pizza, than in Chicago itself?

There is some heated debate about where the first “real” deep dish pizza came from, and well, all we can say is that taste speaks for itself. We do, however, invite you to visit Giordano’s and grab a slice. Or two.

So if after all this sightseeing you’ve worked up an appetite, enjoy a slice of Chicago deep dish pizza and decide for yourself. We bet you’ll find Giordano’s is the best restaurant in Chicago for its world-famous pie. Whether you’re a resident or just visiting, there’s nothing stopping you from starting now. We’ll even ship it to your home so you won’t be without this essential Chicago culinary treat!