Chicago City Guide

Do much traveling over the course of your lifetime, and you’ll surely notice cities have a lot in common with people. Each has its own unique personality and vibe. Each has its own set of values, quirks, and concepts it holds dear. San Francisco is the place to be if you’re into culture and the inner workings of brilliant minds. Miami is a wonder if you’re into color, flavor, and lively nightlife. New York is an eclectic mix of just about everything people like about city life.

Chicago is no different in this regard. Affectionately known as the Windy City, Chicago is another great American location that not only has its own unique vibe, but has a little something to offer just about anyone. For foodies, there’s an ever-expanding culinary scene just waiting to be explored. There’s plenty to tempt sports fans, culture lovers, shutterbugs, and history lovers as well.

6 Reasons to Fall in Love with Chicago

Anyone who’s ever called Chicago home or spent much time visiting can tell you that this is a city that really leaves its mark on you. Even the late, great Frank Sinatra felt the need to sing his heart out in its honor:

“And each time I roam, Chicago is calling me home. Chicago is why I just grin like a clown – It’s my kind of town.” – Frank Sinatra

It’s hard not to be intrigued by a place Old Blue Eyes felt comfortable describing as “his kind of town.” However, it’s also only natural to wonder why you should make Chicago your next vacation when you could just as easily go to New York City, Las Vegas, or Los Angeles. The following are just a few of the many reasons Chicago is truly something to sing about.

1. Chicago’s got history going for it.

These days, Chicago is considered to be a highly desirable place to live or visit. However, that wasn’t always the case. Once upon a time, immigrants who found themselves moving west through the area described it as nothing more than “Indian-filled swampland” that wasn’t worth a second look, let alone serious consideration.

People’s tunes would change once national trade began to rise in importance. Chicago would soon come to be seen as a noteworthy transportation hub between the booming east and the developing west. A multitude of canals and railways were built. Chicago would eventually blossom into a powerful manufacturing and retail location as a result.

It only stands to reason that Chicago would come to make history many times. There was the Great Chicago Fire of 1871, of course. Chicago was also the location of the World’s Columbian Expo in 1893. It was the place where Al Capone ran the streets throughout the 1920s as well. That said, to visit Chicago is to step right into history itself.

2. Chicago’s architecture is second to none.

Chicago has come a really long way from the swampy, muddy mess it was many years ago. Once engineers successfully tackled the problem, Chicago gave rise to some of the most astonishing works of architecture to be seen in America today.

You don’t have to be an architecture expert to appreciate it, either. Even untrained eyes can’t help but marvel at such wonders as the Chicago Avenue Pumping Station, the John Hancock Building, Buckingham Fountain, or the Chicago Merchandise Mart.

3. Chicago is filled with sports history and culture

Chicago is practically synonymous with the concept of great sporting events, and it’s not hard to see why. The Chicago Cubs, the Chicago Bulls, and the Chicago White Sox are quite literally the stuff of legends. After all, who hasn’t heard of the likes of Frank Thomas and Michael Jordan?

Plus, the experience of attending a game is unforgettable. Chicago sports fans are nothing if not passionate about their teams and the games they go to. The stadiums themselves are widely recognized as national landmarks. This is exactly why even those who aren’t diehard sports fans would jump at the chance to take in a Bulls game via floor seats.

4. Chicago is centrally located.

Other major urban destinations – like New York City, Boston, or Los Angeles – may be major travel locations, but Chicago brings something to the table that they don’t. It’s centrally located, so its airports and transportation hubs are capable of servicing the entire country with ease.

No matter what direction you’re going, getting a direct flight right out of O’Hare or Midway is a piece of cake. Multiple major destinations like Salt Lake City, Buffalo, New York City, and many more are just a couple of short hours away – a foreign concept if you’re used to flying out of LAX or JFK!

5. Chicago offers easy access to the water.

Chicago isn’t the first place most people think of when they picture a beach vacation, but natives and regular visitors agree that maybe it should be. Not only does Chicago offer all the culture and diversity of a big city, but the beach is right there as well.

Summer is the perfect time to go biking while you feast your eyes on beautiful views of Lake Michigan. You won’t want to miss the opportunity to enjoy a glorious night walk down Navy Pier or go for a drive along the Chicago River, either. Looking for a classic beach experience? Pencil in some time at North Beach for a day of beach volleyball followed by some cold beer and some local cuisine at one of the many nearby restaurants.

6. Chicago’s people are wonderful people.

Although each city and town in America is filled with amazing people, Chicagoans are truly in a class by themselves. City life in Chicago is as fast-paced and bustling as life in New York City itself. However, residents also demonstrate classic Midwestern values and boundless generosity.

That said, Chicago is the perfect place for you if you appreciate down to earth folks who represent the perfect balance between blue collar appeal and confident sophistication. That’s what Chicago and the amazing people that live there are truly all about.

What to Expect When You Visit Chicago

We’ve established that Chicago is a truly amazing place, and we’ve touched on a few of the reasons why. Now it’s time to discuss the practicalities of what you can expect while you’re in town.

When should you visit Chicago?

Chicago is the type of town where there’s always something going on, so just about any time is a good time to visit. However, most of the noteworthy events, festivals, and scenery take place in the spring, summer, or fall.

If you’re looking to avoid extreme temperatures, then it’s worth noting that January is the coldest month with average temperatures clocking in at around 31 degrees Fahrenheit. Summer heat peaks in July with an average temperature of 84 degrees Fahrenheit.

What’s the best way to get around Chicago?

Like many major urban destinations, Chicago has plenty of options for getting around. For instance, Chicago is famous for its elevated train system (affectionately known by locals as the “L”). Both the trains and the Chicago bus networks offer extensive and very affordable service to all of the city’s neighborhoods, as well as many of the surrounding suburbs. Chicago is also a fairly walkable city.

In fact, many visitors to the Chicago area prefer public transportation to renting their own vehicles while they’re in town, and with good reason. Chicago traffic can be incredibly thick. Also, car rentals, parking facilities, and gas are relatively expensive, so make sure you consider your options carefully.

Fantastic Things to Do in Chicago

There’s a reason Chicago was the city Ferris Bueller chose for his famous day off! It’s positively packed with things to do. Whether you’re traveling solo, with friends, as part of a couple, or with the entire family in tow, you’re guaranteed to find plenty of activities for everyone to enjoy, both together and separately. The following are just a few of the many options you’ll most certainly want to consider.

1. Take in some art at the Art Institute of Chicago.

The Art Institute of Chicago isn’t just any museum. It’s one of the largest, most respected art museums in the country. View over 300,000 major works of art, as well as artifacts and antiquities from all over the world. You’ll have the opportunity to see Japanese prints, fragments of buildings designed by Frank Lloyd Wright, and countless paintings from some of the art world’s most notable masters. Don’t forget to enjoy the museum’s breathtaking views of Millennium Park while you’re there.

2. Pay a visit to Wrigley Field.

If you’re a baseball fan, then you probably won’t want to miss an opportunity to take in a game at one of America’s most famous stadiums. However, that’s not all there is to do at this iconic location. Even if it’s not baseball season when you’re in town, consider taking a seasonal tour that treats you and your travel companions to a peek behind the scenes. Planning on being in town during the winter? Don’t miss a chance to go skating on the ice rink located just outside the stadium.

3. Experience the wonders of the sea at Shedd Aquarium.

Animal lovers and ocean enthusiasts alike won’t want to miss the chance to visit this 75-year-old institution. See and learn about aquatic creatures from all over the world, including frogs from the Amazon, turtles from the Caribbean, lungfish from Australia, and many more. Don’t forget to visit the tide pool exhibit, the otter habitat, and the spectacular mammal shows while you’re there, as well.

4. Enjoy a walk (and some photo ops) along the Chicago Riverwalk.

No matter what time of year you visit Chicago, you’ll definitely want to spend some time taking in the views along the Chicago Riverwalk. Multiple seating areas, walkways, boat tours, and water taxis combine to show you the city’s most beautiful architecture at its very best. Enjoy the fresh air, stretch your legs, and snap a few photos for your scrapbook. Then enjoy a bite to eat and a perfectly blended cocktail at one of the many restaurants and cafes located along the waterfront.

5. Take in an art-house flick at the Music Box Theatre.

If you and your travel companions are suckers for a great film, but aren’t interested in seeing the latest blockbuster, consider visiting the Music Box Theatre. It’s a beautiful two-screen theater where locals and visitors alike can enjoy documentaries, art-house films, and other off-beat movies. Play your cards right, and you might even be able to catch a midnight showing of your favorite cult classic. (P.S. The popcorn here comes topped with real butter.)

6. Get back to nature at the Peggy Notebaert Nature Museum.

Chicago isn’t just a great place to see the beauty of urban life in action. There are also plenty of spots where you can take in a little nature as well. Case in point – the Peggy Notebaert Nature Museum. Learn all about various ecosystems in the area – river, prairie, and so forth – as well as conservation strategies. Engage with hands-on exhibits that the entire family will love.

7. Experience a cocktail the way Al Capone would have loved one.

If you love nothing more than a perfectly crafted cocktail, fantastic bar food, and great music, then you’ll love the Green Mill Cocktail Lounge. During the 1920s, Al Capone and a number of other gangsters hung out there regularly. Today, patrons come from all around to enjoy a fantastic martini and take in a little jazz. This is a popular place, though, so make sure you get there early so you have your choice of seating.

8. Go exploring in Lincoln Park.

Lincoln Park is the kind of place you could literally spend all day (or all week). Named for the 16th President of the United States, the park sprawls along the lakeshore and includes such noteworthy locations as the Lincoln Park Conservatory, the Lincoln Park Zoo, and the Lincoln Park Cultural Center. It also offers access to a wealth of activities, including golf, baseball, a skate park, and plenty of lovely paths just perfect for strolling, jogging, or cycling.

Get Psyched for Your Trip with Regional Interest Literature

As is the case with a visit to anyplace new, you’re sure to enjoy your visit to Chicago even more with a little background information on the city and its history. The right regional history and local interest books can offer you just the introduction to the Windy City that you’re looking for.

Planning on doing as the Chicagoans do while you’re in town and getting around via the “L” train? Get more out of the experience by reading up on this iconic Chicago fixture first. Are you one of the many people who believe it’s the people that make the city? Explore Chicago’s rich cultural heritage with volumes on Mexican Chicago, Italian Chicago, or Irish Chicago.

Are you a diehard news hound? Discover the fascinating backstory behind the Chicago Defender, one of American history’s most noteworthy early papers. You’ll even find special books written by seasoned local experts and historians on the forgotten side of Chicago life, Chicago’s mob history, and more. It’s all right here waiting to be discovered at Arcadia Publishing!