Skip to Content

Visit Chicago! A Little Trivia and a Lot To Do

Chicago, Illinois is one of the world’s greatest cities. Whether it’s holograms, pizza, baseball, Ernest Hemingway or tall buildings you’re after, there’s something for every visitor. Here are some facts and trivia that you may find useful if you visit Chicago.

While you may not find being constantly buffeted by winds particularly funny, Chicago is legendary for its comedy culture. It is regarded as the home of improvisational comedy, and the Second City comedy club has hosted many world-famous stand-up comics over the years.

visit chicago

The home of the Chicago Cubs baseball team, Wrigley Field, is named after the founder of the chewing gum company. Quite apt, given the sticky situation the Cubs have been in over the last couple of years.

Fans of the much-travelled Ernest Hemingway should head to Oak Park, where they can find the suicidal writer’s former home. The house has now been converted into a small museum, with exhibitions about Hemingway’s life and works.

The Sears Tower (renamed Willis Tower in 2009) is the tallest building in the US, and some would argue, the world. Constructed in 1974, and has The tower 108 stories as counted by standard methods, though the building’s owners count the main roof as 109 and the mechanical penthouse roof as 110.

While not exactly a foodie heaven, Chicago can claim to be the birthplace of two not-so-gourmet foodstuffs. The hot dog and deep dish pizza both originate there.

The Buckingham Fountain in Grant Park is one of the biggest fountains in the world.

If you like your attractions on the dark and grizzly side, then there are plenty of options available. The more sick-minded tourist may like to visit the home of notorious gangster Al Capone, or the site of the Valentines Day massacre. If you like things more on the grizzly rather than outright criminal side, try the International Museum of Surgical Science. It’ll tell you more than you really need to know about cutting into bodies and having a dig around with all manner of equipment.

Feeling arty and need a quick dose of culture in the Windy City? Why not try the Museum of Contemporary Photography or Smith Museum of Stained Glass Windows

Chicago also does music rather well, particularly the blues. You can find Howlin’ Wolf’s guitar at the Chicago Blues Museum, while Willie Dixon’s Blues Heaven was where many of the greats – including Muddy Waters – recorded.

The world’s biggest collection of holograms can be found at the Museum of Holography.

The Field Museum hosts the biggest Tyrannosaurus Rex skeleton ever discovered.

Chicago is a city filled with surprises. No matter what the season, be prepared to fall in love. It has the most amazing architecture, a splendid location on Lake Michigan, great pizza and enough world class museums to keep anyone occupied for as long as they would like.

Visit Chicago

Did you know? The surprising reason Chicago Is called the “Windy City” – It’s got nothing to do with the weather! The nickname, the “Windy City” wasn’t describing the weather but the people. Nineteenth-century journalists first gave Chicago this designation when criticizing the city’s elite as “full of hot air.” More and more journalists—from Cincinnati in particular—began using the “Windy City” jab, and it stuck.

Here are just a few tips for enjoying the Windy City.

Planning Your Trip

Use the Chicago transit authority’s website to plan your trip. You can put in the address where you will start your trip and where you want to end up and the site will tell you exactly how to get there. It even lets you put in the time of day you want to travel. It will even tell you how long you should have to wait for your next connection. Purchase a day pass, 1, 2 or 3 days. If you are going to be in town more than 3 day buy the 7 day pass it will be the better buy. The day pass is good on the “L” (elevated rail or what most us call the subway) and on the bus and can also be used to get in from Midway airport. We bought ours at the “L” Station at Midway in a machine.

Hop on a Trolley Tour

Take one of the Trolley Tours. It is amazing how much this helps you to get your bearings. We took a hop on, hop off tour; there are several companies that offer these. We rode almost all the way through the tour and then got off at the Art Institute. It helps if you have an early start to your day, this way you can go all the way through one time and then get off at the places where you would like to spend more time. There are multi day passes available.

Cruise Down the River

Take an architectural river cruise of the Chicago River. You will see the city from a perspective that you won’t get from anywhere else. The range and scoop of the buildings is amazing and the river itself has a story to be told. There is a live tour guide who is a font of information. Tours start from Near the navy Pier.

Shop on Michigan Avenue 

Walk up Michigan Avenue and enjoy window shopping, you will find all the major designers have stores there. While you are there stop at the Visitor Center and get all the local information that you will need for a great visit. For anyone with young daughters, nieces or granddaughters the American Girl Store is a must.

Enjoy the Navy Pier

Walk on Navy Pier. From here you can take a cruise of Lake Michigan, visit the Stained Glass museum (free) take a Ferris wheel ride, watch a play at the Shakespeare Theater or just go and have lunch or dinner at one of the many restaurants. We also enjoyed the displays along the pier of the vehicles that have been pulled out of Lake Michigan.

Get Your Exercise

Rent a bike and pedal your way around some of Chicago’s ethnically diverse neighborhoods. There are several different companies who do this. You can also rent a segway.

See Chicago from the Heights 

Go to the top of the country’s tallest building the Sears Tower. The views from the observation deck are amazing. Just the ride up is something that you don’t get everyday. There is a display of pictures of Chicago and her more famous people on the observation deck.

Be Impressed by the Arts 

If you can only do one museum make it the Chicago Institute of Art. This is a world class museum that really is in a class by itself. A very deep collection of old masters, American artist and impressionist and post impressionists.

See a Show

Get tickets to one of the shows, Broadway or comedy take your pick, both can be found in abundance. I am going to suggest that you buy them as far in advance as you can since they are very popular.

Eat Pizza

Be sure to try some Chicago deep dish pizza. It is an institution that has spread to the far corners of the United States you must try it whehre it all began.

Stay at a B&B

Flemish House off of North Michigan Ave is a downtown B&B and it is amazing. The location is fabulous and the hosts very welcoming. You don’t get a cooked breakfast but you get what you need in your apartment everyday to make your own breakfast. Without doubt your bed there was the most comfortable that you have ever slept in and all at a very reasonable price.

Chicago is a city that has an interesting past and an exciting future. There are so many things to see and do that two weeks would not be too much to spend here. But no matter how many days you have you will be able to fill them with fun and fascinating things to do.

Please Share and Follow