I lived in Illinois for 13 years and only visited Chicago… once. 😅

I lived near the bottom of Illinois, about 50 minutes from the Kentucky border, making Chicago an approximately 6-hour drive north. It sits at the top-east of the state, right on the great Lake Michigan, and is known for being the residence of Barrack Obama, Kanye West’s hometown, the Bears football team, the Cubs (World Series Champs!! FLY THE W!!!), White Sox, Willis Tower, The Bean, Magnificent Mile, Navy Pier, canals that run through the city, and much more. There is, unfortunately, an infamous danger element to Chicago, however, if you stay alert and aware, and in the more populated, touristy areas, it’s like any other major city.

Hotels in Chicago are like any large, metropolitan city – overpriced. To stay in any downtown hotel, particularly along the river walk, an average room costs $300 to $400 per night. We chose to stay near the airport, at the more economically conscious Hyatt Regency O’Hare hotel (would recommend), located at 9300 W Bryn Mawr Ave, Rosemont, IL 60018. It was much cheaper, around $100 per night, and we just took the Amtrak into downtown. A one-day Amtrak pass costs $10 per ticket, with several other various passes available, like 3-day, 7-day, annual, etc.

We headed to downtown, with our goal being Navy Pier, as we planned on taking a scenic boat tour through the waterways that run right through downtown Chicago. As we walked from the Amtrak station to the pier, we passed iconic attractions like a 30-foot statue of Abe Lincoln giving the Gettysburg Address next to a modern-day man (sadly gone – it was moved to a museum in Peoria, Illinois), Willis Tower (formerly known as Sears Tower), the Tribune Tower, The Mart, the Trump International Hotel, and more. We’d end up seeing all these buildings from the boat, which offers a better view, and learning their histories while on the tour.

We toured with Chicago Cruise Lines, which offers a variety of cruises – we chose the Architecture Cruise. All their cruises take around 90 minutes (except the one with fireworks) and tickets for all cruises are $45 (age 12+), $24 (ages 7-12), and children under 6 are free. It’s a tad pricey, but also a fantastic way to tour the downtown skyscrapers and historic buildings while getting live commentary from the guide. The daily tours run periodically, however please be advised, there aren’t a ton of them – 4 to 6 per day, depending on time of the year. My advice is to book in advance and definitely be at the pier when required. The last tour is typically around 4pm or 6pm, depending on when you go and which tour. The Chicago Cruise Lines website has all the exact times listed for the different times of the year: https://www.chicagoline.com/.

The boat is wide open, so you get a lovely 360-degree view of the city as you slowly float your way through the canals. We went in June, on the last tour of the day, so the sun was setting and it was cooling off, making it was very pleasant and enjoyable. The guide was extremely knowledgeable about the city of Chicago and gave loads of information about the various buildings lining the canal. We learned about the Merchandise Mart– known locally as “The Mart” – which is so large that it had its own zip code until 2008. When it opened in 1930, it was the largest building in the entire world.

Then there is the Civic Opera House, which opened its doors in 1929, and is still the second-largest opera auditorium in North America, one-upped only by NYC’s Metropolitan Opera House. There’s also Marina City, which sits directly on the canal, and is one the most famous “mixed residential” (owners and renters) buildings in the entire world. To rent a one-bedroom, it’s between $1650 and $1750 a month, which is pretty equivalent to many California prices. We learned about several other iconic buildings as well.

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As we were walking back to the Amtrak station, we passed the Tribune Building, which has a pretty awesome feature: chunks of rock and building fragments from very famous places around the world. These include: Pearl Harbor, House of Commons in England, Mt. Rainier in Washington, Omaha Beach in Normandy, Petra, Antarctica, the Great Pyramid of Giza, Taj Mahal, the Alamo, the Great Wall of China, Ab Lincolns Tomb, Norte Dame in Paris, the Berlin Wall, and many more. Some of these stones and building fragments are much too high up to touch, but a lot are within reaching distance.

The next day we headed to Millennium Park, where the famous Bean is located. Officially called Cloud Gate, I’ve never heard anyone call it that. Growing up in Illinois you hear about it all the time and it’s essentially exclusively referred to as “The Bean”. I was honestly unaware it had a different, formal name until researching it before we went. A public sculpture, it was installed in 2006, and is completely free to view (parking will cost $$). Truthfully, I was rather surprised by how dirty it was up close, because from far away, it looks so clean and shiny. It needed a good bath.

Within spitting distance of The Bean is Crown Fountain (please see below), named after the Crown family, a very prominent clan in Chicago during the early 1900s. It’s a favorite spot for locals during the summertime, especially children, as it can get very hot and muggy. Plus it’s also free. It’s designed with a video display that is used for various things throughout the year.

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Overall, I’m extremely grateful I was able to visit Chi-Town before moving out of state. I was disappointed I never got to see the Bears play at Soldier Field, however, I watched them annihilate the Rams at the Dome in St. Louis, so all ends well there. While Chicago does get a bad rap, this city still has a lot of good offer. There’s an enormous amount of history here, and what we got to experience was seriously just the tip of the iceberg. Please don’t pass up visiting this historic city.

And with that, I say, DA BEARSSSS! 🐻🧡💙