Chapter 1: The Journey Begins

Traveling from Wisconsin to New York along Interstate 90 presents one major hurdle: the bustling Windy City.

For the past two years, we've been making regular trips on I-90. If you're familiar with this route, you know it's expansive, multi-laned, and often congested with heavy traffic and construction delays. The drive from Wisconsin to New York (and even as far as Maine, as we did this summer) is straightforward, but can test your patience. You simply hop onto "the 90," as locals refer to it, and hit the road.

However, the journey is not without its challenges. Tolls used to be a significant inconvenience. Navigating the right lanes, carrying enough coins, and enduring long waits at toll booths could be quite time-consuming and costly. Fortunately, the introduction of transponders has transformed this experience. Now, you can drive through toll areas without stopping, making the process much smoother. In fact, in places where toll gates have been modernized, you might not even realize you've passed one. Many states, including New York, are also removing traditional toll barriers.

These transponders automatically register your vehicle and charge the appropriate credit card. We've been using an EZ Pass for over two decades, and it has definitely simplified the tolling experience.

Section 1.1: Ongoing Challenges

Despite these advancements in toll collection, the ongoing need for road construction and infrastructure upgrades remains a significant issue. The thought of navigating downtown Chicago often induces anxiety—not just because of the high volume of traffic, which can be daunting, but also due to the construction-related bottlenecks. Earlier this year, we found ourselves stuck for two hours in the express lanes due to construction lane closures. It was incredibly frustrating.

On our return journey to Wisconsin, we completely bypassed Chicago. While this added extra time to our trip, it was not always the most practical or cost-effective choice. What could have been a single-day journey turned into two days because we had to stop for the night. But we experienced less frustration as a result. So, one must carefully consider their travel strategy based on time, finances, and patience.

Subsection 1.1.1: A Pleasant Surprise

This past December, we drove through Chicago on I-90 in both directions. On our way east, we were pleasantly surprised to see that the construction was finally complete! It's hard to express how long the expressway had been under repair. However, despite the absence of construction, heavy traffic remains a constant in the city. Drivers, well-acquainted with the roads and exits, tend to speed—often exceeding the speed limit. Expect to be cut off, tailgated, or face difficulty changing lanes. This can create a dangerous and stressful environment. We usually plan our drive through the city late at night on weekdays to avoid these issues.

Yet, this time, we made excellent progress. We arrived in Chicago earlier than anticipated, around 7:30 PM on a Monday. To our delight, we encountered no traffic and didn’t have to slow down at all. We zipped through the Windy City on I-90!

It may seem trivial, but it was absolutely wonderful! No construction, no traffic jams, no accidents blocking lanes, and just a handful of reckless drivers. It felt like a breeze!

Chapter 2: Reflections on the Journey

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