Exploring Chicago: Sunset Views and Unique Experiences

Intro

It’s finally the last leg of my Los Angeles – Las Vegas – Chicago trip. You can see the first part of this trip here:

A Day at Universal Studios Hollywood: Attractions and Experiences

Halloween Horror Nights 2025 in Hollywood: A Memorable Night

Your Guide to The Wizard of Oz Show at The Sphere in Las Vegas

Universal Horror Unleashed: An Honest Review

I was arriving in the Windy City from Las Vegas, and the time change had already made this day go even faster. I was hoping to see a few things before the night tho.

In this post I am going to show some things to do in Chicago, and will finish with more tips on the next and last post of this saga.

Arriving to Chicago

My flight landed in ORD Chicago O’Hare International Airport, and on the way in I could see the famous skyline next to the Lake Michigan.

The giant airport was easy to walk around, and I was looking for the Blue Line train into the Loop or Downtown.

My first sunset in Chicago

I visited Chicago for a couple of days in the same week of September in 2013. I liked the city, but the weather unfortunately makes it a little bit unwilling to visit for me at least. I had a stop a couple of years ago in ORD coming from an international flight, but did not really go into the city. The train from ORD to the Loop takes more than an hour, and did not have time then.

Now, I was finally back for a few nights, and wanted to start with a great sunset in this big city.

From a building in The Magnificent Mile, the famous street in Chicago, I was able to see this beautiful sunset, confirming my last leg on this short trip.

Chicago surprises me in the best way. Home to almost 3 million people, it’s a city that perfectly mixes big-city energy with that easy Midwestern warmth. Sitting right on the edge of Lake Michigan, its skyline is stunning—massive towers like the Willis Tower and John Hancock Center rise above the water, creating one of the most beautiful views in the U.S. Every neighborhood feels like its own little world. Between the food (yes, the deep-dish really is worth it), the music, and the museums, there’s so much to do without it ever feeling overwhelming. It’s one of those cities that somehow feels both impressive and inviting at the same time.

As I approached my hotel, I walked the Magnificent Mile, with a view of the John Hancock Center (875 North Michigan) where I would go the next day for 360 Chicago, the Observation Deck.

Starbucks Reserve

One of the coolest spots I visited in Chicago was the Starbucks Reserve Roastery on Michigan Avenue. It’s the largest Starbucks in the world, spread across five stunning floors that feel more like a coffee museum than a café. You can watch beans being roasted on-site, try exclusive drinks you won’t find anywhere else, and even grab cocktails at the rooftop bar. Whether you’re a coffee lover or just want a unique Chicago experience, it’s absolutely worth stopping by.

Hilton Chicago/Magnificent Mile Suites

My stay was fantastic. I went from a expensive but run down motel in Hollywood, to a regular hotel in Las Vegas, to a cheap but amazing suite in a Hilton in Chicago.

I was about to sleep so well the next couple of nights lol.

Lou Malnati’s Pizzeria

The next day, and after having an Architecture Boat Tour (that you will see in the next post), I went to Lou Malnati’s Pizzeria, where I had to get one of the typical dishes of Chicago: the deep dish pizza. Surprisingly, the Colombian flag was right upfront the entrance.

Lou Malnati’s Pizzeria is a Chicago classic and one of the best places to try authentic deep-dish pizza. The crust is buttery and crisp, the cheese stretches for miles, and the chunky tomato sauce has that perfect balance of sweet and tangy. It’s casual, cozy, and feels like the kind of place locals have been going to forever. If you’re in Chicago, grabbing a slice (or honestly, a whole pie) here is a must.

I chose the personal size and oh my. I actually enjoyed it more than I anticipated. The texture was amazing. The taste immaculate. I thing I would definitely try it again sometime.

Harry Potter Store

Also located in the Magnificent Mile, The Harry Potter Store in Chicago is a magical stop for any fan of the Wizarding World. From the moment you walk in, it feels like stepping right into Diagon Alley, with shelves full of wands, robes, and themed treats. The decor is immersive, full of little details that make you feel part of the story, and there are plenty of photo spots for the perfect souvenir shot. Whether you’re a lifelong fan or just curious, it’s a fun and enchanting place to explore in the middle of the city.

I like that it is more themed than the one in New York City.

And it is also huge! The store kept going and going.

The dining area was also bigger and had tables and chairs, unlike the one in NYC. And of course they offer the famous butterbeer.

Which I had to purchased, even though I had had it a couple days ago in Universal Studios Hollywood. I also got the little cauldron cake, and SAT DOWN to eat this lol.

360 Chicago Observation Deck – Round 1

The time had come to visit the 360 Chicago Observation Deck. I had tickets on my phone, and the time was coming very soon. I had also booked the access to Tilt, which you can see in this picture.

360 Chicago Observation Deck is one of the best places to take in the city’s skyline. Located on the 94th floor of the John Hancock Center, it offers incredible views of Lake Michigan and the streets stretching far below. The highlight is TILT, a glass platform that literally tilts you forward over the edge for a thrilling perspective of the city. It’s a mix of excitement and awe, and whether you go during the day or at sunset, the views are absolutely unforgettable.

Got in at 3 PM, and there was virtually no line lol. Passed security and went inside right away. The elevator does not really give a show like in other Observation Decks.

One of the first views I had was the Navy Pier which I would visit the next day.

It started getting foggy, but I managed to take a pic of the northern side of Chicago and towards the Lake Michigan.

Finally, the fog invaded the view. The whole skyline was covered, and the main buildings by The Loop, to the south were not fully visible.

I still was able to see the Willis Tower and a few others. Hopefully, the fog would not last long.

On top of the fog, the TILT was not working. The line had increased and there was no repair in sight. Apparently, the building management had the glass cleaned and locked the TILT, and forgot to unlock after they were done.

I did not want to waste my time, so I left, not without getting a new ticket for the next day, since the TILT was not working.

Giordano’s

The next day, I went to get lunch at Giordano’s, another Chicago legend, famous for its stuffed deep-dish pizza that’s basically a gooey, cheesy masterpiece. Each slice is thick, rich, and loaded with layers of cheese and sauce inside a buttery crust that feels more like pie than pizza. The atmosphere is casual and welcoming, making it a great spot to relax after exploring the city. It’s definitely one of those must-try Chicago food experiences—just come hungry, because one slice can be a meal on its own.

I wanted to try the thin slice pizza, and I got a side of parmesan fries. I ate the whole thing in one seat, I was so hungry, but this was also very delicious.

360 Chicago Observation Deck – Round 2

I was back in 360 Chicago Observation Deck after a long day of exploring, and this time the weather seemed a bit better. They scanned my new ticket, and I went back up. I was really hoping that The TILT was really working this time around.

The views were even more incredible this time around. The different colors and hues of blue and green in the Lake Michigan felt like out of this world.

The perception of the curvature of the Earth from up here was incredible. I know it’s crazy because it’s not too high, but the effect is real. I am glad I came back to this Observatory, and for free!

The Observatory is huge, and has this bar area, and a lot of space just to lay down and relax.

And for the last pic of this post, I finally did it. I waited in line and stepped on the TILT. It looked scary and WAS scary. The shoes slipping down, while the platform leaned was the scariest part. If the previous days of Halloween scares in Los Angeles and Las Vegas had not scared me enough, this one did it for sure.

But there’s still a lot more to cover about Chicago, and that will happen in the next post.