Let's Take a Day Trip

CHICAGO, Ill. — It is commonly the punching bag for conservative talking points regarding crime. Because of its geographic location, it’s often overlooked as a “go-to” destination like Los Angeles, Miami, and New York City. Like most Midwestern cities, the City of Big Shoulders is known for its cold nature.

While Chicago can have harsh winters and violence, which leaders should continue to work on reducing, the Windy City is a world-class city with a skyline that pierces the heavens. Everything you want in a major city, Chicago, has it.

Take a day trip with me to America’s third-largest city.

Getting around Chicago

Public transit must be top-tier for a city to be functional. In Chicago, that’s certainly the case. Two major airports serve the city – O’Hare and Midway International Airport. O’Hare is the largest of the two on the city’s northwest side. Midway is a hub or “focus city” for Southwest Airlines on the city’s southwest side. A couple of other carriers, like Delta, fly into Midway. More than likely, if you’re flying any other airline other than Southwest and a few select Delta flights, you’ll fly into O’Hare.

Regardless of which airport you arrive in, both are served by the Chicago Transit Authority (CTA). For $5, you can take the Blue Line train from O’Hare to downtown Chicago (The Loop) or the Orange Line train from Midway. Here’s the cool thing: The Blue Line runs 24 hours a day from O’Hare to The Loop.

You may be thinking, why is that significant? There is no other city in the United States of America where you can take the train directly from the airport to the central business district 24 hours a day — but you can in Chicago.

I’m sure you can take a train all day and night from Newark’s Liberty Airport to New York City, but EWR isn’t in New York City. So, again, Chicago wins. Keep in mind there isn’t a train at LaGuardia or JFK. You can take a train to those airports and connect to a shuttle or bus. However, there isn’t a train serving those two airports 24/7.

Back to Chicago, the Orange Line isn’t 24/7, but the CTA’s website says a few trains run after midnight during the week. Be sure to check the train schedules ahead of time. While in the city, the CTA will be your mode of transit when getting around. You should download the Ventra App to buy a bus or train ticket. The one-day pass is $5, and the three-day pass is $15. For all things CTA, click here.

Things to do while in Chicago

Imagine sitting at the beach with beautiful blue waters roaring towards the shore. A cool breeze blows by you, and a picturesque skyline towers in the background. It’s a perfect blend of nature and architecture. This is what makes Chicago unique.

I’m not putting down Los Angeles, but when you go to beaches in Southern California – more often than not – you aren’t within Los Angeles’ city limits. And if we’re being honest, Miami’s skyline isn’t comparable to Chicago and most of the beaches there aren’t in the City of Miami. And because Chicago sits on Lake Michigan, you don’t have to be concerned about sharks.

My point is that you get the best of both worlds in Chicago during the summer. You have the “big city” New York-like skyline with endless shorelines that you’d expect in SoCal or Miami. That’s Chicago.

Beaches aside, Chicago offers something for everyone. Do you like Broadway performances? Chicago has the Chicago Park District Theatre. Do you want to shop at high-end retailers like Gucci? Chicago has The Magnificent Mile. If you’re into sports, you already know Chicago has all five pro teams scattered across the city.

The parks are the city’s hidden gems! If you don’t do anything else, I suggest going to Millennium Park. The views from there are breathtaking, and it’s a nature oasis in the middle of the concrete jungle.

While in The Loop, take a boat ride tour along the Chicago River as it twists and curves through downtown and see Chicago’s iconic skyline towering over you.

Lastly, if you know me, I love going to the casino. They have a Bally’s Casino downtown and are building a state-of-the-art casino where Bally’s will be located. Its current location is temporary.

I’ll be honest, though; I don’t care for Illinois casinos; I go to Indiana, but that’s neither here nor there.

Food. Let’s talk about food

After you’re done gallivanting across The Loop, you’re probably hungry. My favorite thing about Chicago is the food. I’ve always had a good food experience in the city. I’ll preface this by saying my pallet may be different from yours, but here are some of my favorite spots in The Loop.

Pizza: Lou Malnati’s

Soul Food/Bar: Kitchen and Kocktails Chicago

Brunch: Yolk

Of course, there are other Chicago staples like Harold’s Chicken, Sharks, Jim’s Original, Italian Fiesta, and the original Home Run Inn that I can name. However, I’m focusing more so on The Loop.

On that note, what’s interesting about Chicago is there are 77 neighborhoods in the city. You can have the time of your life in Lakeview, the Near West Loop, and Hyde Park, to name a few. One of my favorite buzzing areas is Lakeview, near the Southport Brown Line station. Grab a taco at Tuco And Blondie or a burger at Corridor Brewery & Provisions.

Quick mentions before addressing the elephant in the room

While in the city, take a helicopter tour to see Chicago’s majestic skyline from above, explore some of the city’s world-renowned museums, and experience Navy Pier. See Chicago from the Willis Tower’s (Sears Tower) Skydeck then venture outside The Loop.

Go on an early morning jog in one of the forest preserves in Cook County. Perhaps, grab a rental car and visit the Woodfield Mall in Schaumburg, Illinois. Check out Six Flags Great America in Gurnee and then gamble at the American Place Casino.

Check out the Indiana Dunes over in northwest Indy and then go on a wine tour in southwest Michigan.

I know you’re thinking man we’re going way outside of the city, but Chicago’s influence goes beyond its borders.

Now to the elephant, and then I must go on…

Yes, it’s true. Chicago is a violent city. It breaks my heart to watch grieving parents crying on the news because their innocent child, who wasn’t the intended target, gets gunned down. It is also true, watching this on the news breaks my heart when I’m in any major city.

Crime isn’t unique to Chicago.

I watched people do and sell drugs on the light rain train in Minneapolis. I’ve seen people fighting on the subway in New York City. I’ve heard gunshots while visiting Atlanta. As a former T.V. news reporter, I’ve covered sad, tragic stories from gun violence in Grand Rapids, Michigan, to the opioid crisis in the nation’s Heartland in Davenport, Iowa.

The moral of the story is crime is everywhere.

Chicago isn’t a playground. Be mindful of your surroundings regardless of where you are.

But remember — have fun.

Until next time, enjoy your stay in my hometown, Chicago.