Chicago, IL

Photo taken of an exhibit at O’Hare International Airport

See Chicago through a river cruise

I recommend starting your Chicago sightseeing with a River Cruise by the Chicago Architecture Center (CAC). It’s a relaxing and informative 90-minute cruise along the Chicago River and enables you to view the city seated on Chicago’s First Lady (first photo above). Snap photos of top attractions like Chicago’s tallest building, the Willis (formerly Sears) Tower (last photo above on the right), and ride under one of the draw bridges that line the River.

CAC’s River Cruise highlights the many unique and impressive structures in Chicago. You get to learn about history, architecture, and the famous personalities who left an imprint on the city.

Chicago Riverwalk

On the CAC River Cruise, I learned that Chicago’s Riverwalk is one of the newer riverwalks in the US. The city completed the most recent phase in 2016. It shows; the Chicago Riverwalk is clean and a nice way to meander along the water. Head east toward one of the piers to breathe in Lake Michigan.

The Loop

For a first time visit to Chicago, you must visit the Loop, which is the central business and downtown district. Named after the elevated “L” train which loops the area, the train and buses are an alternative to walking (although I find walking in the city easy and enjoyable). The Loop is south of the Chicago River.

Millenium Park

Millenium Park is located in The Loop. In Millenium Park, visit Cloud Gate (aka “The Bean”), which is iconic to Chicago. I associate The Bean with Michael Jordan and the Chicago Bulls basketball team. The Park itself is covered in grass and trails. Jay Pritzker Pavilion (second photo on the right above) was designed by Frank Gehry and is home to music festivals and performing arts events. Also designed by Frank Gehry, the BP Pedestrian Bridge (last photo above) connects Millenium Park to Maggie Daley Park.

Maggie Daley Park has many activities for the whole family, such as a climbing wall, mini golf, play garden (aka playground), roller blades & micro scooters, and tennis courts.

Public transportation in Chicago

Chicago has an efficient public transportation system. Connections between my trains and buses ran smoothly. They even had a button at one of the bus shelters that the visually impaired can press for bus time arrivals (third photo above).

Like I mention in my solo travel post, I usually take public transportation to and from the airport. From Chicago O’Hare International Airport (ORD), follow the signs for ground transportation then the Chicago Transit Authority (aka CTA) Blue Line. The CTA accepts contactless payment on buses and the “L” train lines.

Unlimited ride passes & a Ventra card

To utilize unlimited ride passes, you will need a Ventra card. For a weekend trip of 3 nights and 4 days, I bought a 3-day pass for $15 for the Taste of Chicago in September of 2025. This was a great value since the fare to/from O’Hare was $5 each way. “L” train fare on the various lines was $2.50 each and buses were $2.25 each. Up to two transfers are free within two hours. I definitely saved money with the pass.

You can buy a Ventra card (first photo above) once you take the long walk toward the CTA station from O’Hare. I found there were two sets of kiosks. The first set of machines seemed older and wanted to charge me for a Ventra card. I decided to go to the second set of kiosks, which were taller and looked newer. They had the contactless payment symbol. Although I found that contactless payment wasn’t available at any of the machines, the second set of kiosks didn’t charge me for a Ventra card.

Farewell to the Signature Room

Located off the Magnificent Mile, north of The Loop, I sat at the bar at The Signature Room in May 2023. The Signature Room was a fine dining restaurant that wrapped around the 95^th Floor of the John Hancock Center. It had panoramic views of Chicago’s skyline and shoreline. I was told the best view was from the ladies’ restroom. Sure enough, the rumors were true. I snapped the photo on the right from the ladies restroom. Alas, The Signature Room closed in September 2023. The Signature Room has since become the 360 CHICAGO observation deck.

Chicago is a must see

I recommend visiting in the late spring or early fall. Depending on how far you’re coming, it can be a holiday weekend getaway. Both times I’ve visited, I’ve only brought a backpack and purse. Chicago should be on your travel list, especially if you are drawn to an urban environment. It’s a bustling city with top notch cuisine and Midwestern humility. I will be back.