Chicago is a city full of amazing architecture, vibrant neighborhoods, and incredible food. As someone who loves exploring a mix of modern wonders and historic landmarks, I found it to be the perfect place to dive into both worlds. I can’t wait to share all the unique experiences I had in this lively, ever-evolving city.
Lodging
We stayed at the Hyatt Place River North, which turned out to be the perfect home base for our Chicago trip. The location was ideal—close to all the major spots I’d planned to visit. The hotel was spotless, and the neighborhood felt safe and welcoming. One of the highlights was the complimentary breakfast, which offered a variety of options to suit all tastes, and we always left satisfied and ready for the day. While we didn’t get a chance to try the attached restaurant, the food looked great, and the atmosphere was inviting. I’d definitely recommend this hotel to anyone exploring the city.
Attractions
Like any major city, Chicago is packed with must-see activities, and the Windy City certainly didn’t disappoint! I’m excited to share a few of my favorites from the trip!
To get the most out of our visit, we bought the Go City All-Inclusive Pass, which was such a convenient and budget-friendly way to explore. With this pass, you pay a flat fee based on the number of days you need, and it covers over 37 attractions (though each city’s options vary). We chose the 3-day option, which costs about $190 per person. While that might seem like a lot upfront, it ended up being completely worth it! Most attractions we wanted to see were typically $30-$50 per person, so even after four or five stops, the pass pays for itself. We managed to hit over 15 attractions, so we definitely got our money’s worth.
With the Go City pass, you can customize it for however many days fit your plans. Every activity we did in Chicago was included in the pass, and I’ll definitely be using it in other cities as I travel.
Cruises
One of the top highlights of our trip was the cruises we took—they were incredible experiences! First, we did a 75-minute River Architectural Tour, which shared the fascinating history behind the many buildings lining the iconic Chicago River. The guide’s insights and the close-up views of Chicago’s architectural gems made it unforgettable. Then, we switched it up with a 30-minute speedboat cruise on Lake Michigan, giving us incredible views of the skyline from the water. The two cruises were completely different experiences, but both were unforgettable in their own way.
Bus Tour
The famous Hop-On-Hop-Off tour with Big Bus is a double-decker bus that takes you around the city, stopping at all the iconic landmarks. You can hop off to explore and then get back on when you’re ready to move on.
They provide headphones for an audio tour that shares the city’s history, architecture, and notable figures. Some might think the audio tour is a bit cheesy, but I actually enjoyed it because it helped me learn more about Chicago, which is often called “The Second City.” That nickname comes from the Great Chicago Fire, which wiped out much of the city and required it to be completely rebuilt, making the Chicago we know today the “second” version.
We even had a great bus driver who added her own insights about the city, sharing stories and tidbits you wouldn’t hear in the usual audio tour. I would highly recommend using the bus to learn more about the city and to see it from a new perspective.
Skyscrapers
Chicago is known as the nation’s architectural capital, the birthplace of skyscrapers. The city boasts an impressive skyline with numerous skyscrapers, two offering incredible views for tourists.
One of these is 360 Chicago, located in the John Hancock Center. From the 94th floor, you can look out over the city, and there’s an optional attraction called The Tilt. This feature puts you on a movable glass platform that tilts you down to look straight at the ground below. We opted out of this extra add-on since it wasn’t included in our pass, and I had no desire to try it.
What sets 360 Chicago apart from the Skydeck in the Willis Tower (though locals still call it the Sears Tower) is the atmosphere at the observation deck. 360 Chicago has a restaurant and a bar, creating a laid-back vibe with comfy chairs, inviting you to relax and enjoy the view. In contrast, the Skydeck takes you up to the 103rd floor, offering stunning views as well, but I felt it was a bit more rushed and less relaxing. While you can take your time there, the absence of seating makes it feel less comfortable.
At 360, there’s The Tilt, while the Skydeck features The Ledge, a glass box that extends from the building. You can walk out on it to take in the breathtaking views and look down below. Each group gets 90 seconds on The Ledge, allowing plenty of time for photos. This was included in our pass, and to our surprise, the wait wasn’t as long as we expected. I really enjoyed the experience at both towers.
We visited one during the day and the other at night. We aimed to go at sunset, but by the time we reached the observation deck, it was fully dark. I’d highly recommend visiting at sunset or nighttime; seeing the city all lit up is absolutely stunning! While the daytime views are cool, the nighttime experience was way better.
These were some of my favorite attractions during our trip. We packed in even more activities using our pass, including visits to the aquarium, a ride on the Ferris wheel (fun fact: the first-ever Ferris wheel was in Chicago!), biking through the city, exploring some museums, and bowling with pizza. The pass was an incredible way to experience everything the city has to offer!
Getting Around
We took the train from the airport to our hotel because it was cheaper and faster than driving. For our return trip, though, we opted for an Uber for the same reasons. The train system, known as the L, is a cool way to get around the city, with its elevated tracks giving you a unique view and a glimpse into its deep historical roots.
While we also used the Big Bus and rented bikes, we mostly walked everywhere. The attractions are relatively close together, especially if you take the bus part of the way and then walk the rest. I can’t imagine driving in this city—it seemed chaotic! Thankfully, Chicago is very pedestrian-friendly, making it easy and enjoyable to explore on foot.
Sites
There are so many incredible sites to see around the city, and aside from the towering architecture, my favorite building has to be the Chicago Tribune. Its unique design features blocks from all over the world, each with inscriptions. If you walk by, see if you can spot them all!
The Bean is another must-see. It’s always packed with people, but it’s still a fun experience to check out. Buckingham Fountain is absolutely stunning—it’s huge and beautifully designed.
The Plaza of the Americas honors various countries with flags lining the area. There’s also a statue of the President of Mexico, which I believe was a gift. And don’t miss the cool angel wings nearby; they’re perfect for a photo op!
The Riverwalk was one of my favorite places! It runs along the Chicago River and has a lovely path for pedestrians. Locals and tourists alike were out walking, running, and biking, and the views of the buildings are fantastic. If you’re lucky, you might catch the bridges rising to let larger boats through. It’s fascinating, especially knowing that these bridges are over a hundred years old!
On our last day, we headed to Lincoln Park, which is a bit outside the city. It turned out to be the perfect activity before our flight. The zoo there is free and features some amazing animals, plus the park offers great views of the city skyline.
Food
Xoco
We ate at this amazing Mexican restaurant called Xoco, which offered a ton of options. While it wasn’t traditional Mexican food, it was absolutely delicious! The churros were incredible. I especially enjoyed their seasonal Smoked Chicken and Pear Salad; the flavors blended together beautifully. We tried a few other great dishes, but the standout items were definitely the salad and the Baja Chicken Torta. The restaurant’s location was super convenient, too, as it was directly across the street from our hotel.
Lou Malnati’s
Deep-dish pizza is a must-try on any trip to Chicago, and Lou Malnati’s did not disappoint! The atmosphere in the restaurant was really nice, but it was definitely busy. We had a reservation for 8 PM, and it took a little while before our food arrived. Keep in mind that the pizza takes about 45 minutes to cook. To tide us over, we ordered a salad—the Chicken BBQ Club Salad—and it was amazing! The pizza we tried included The Lou and the Malnati Chicago Classic, both of which were incredibly tasty. I would definitely recommend stopping by for a slice!
Angry Octopus
One of the best-kept secrets in Chicago is this family-owned restaurant that serves amazing food! They offer a fantastic variety on the menu, and everything we ordered was delicious, leaving everyone in our group satisfied.
We had tried some classic Chicago dogs throughout the city, and I can confidently say this was the best one we had! I opted for a BBQ chicken wrap, which was incredibly fresh and flavorful. The staff was also a highlight—they were friendly and attentive, making our experience even better. If you’re in the area, this place is definitely worth a visit!
Portillo’s
Another famous restaurant in Chicago that we tried was a delightful experience. The atmosphere was vibrant and unique, filled with energy from the bustling crowd. Although it’s technically a fast-food restaurant, don’t be surprised if you find yourself waiting up to an hour for your food—it’s that popular!
The location was convenient, right by our hotel, which made it easy to stop by. One of the standout items on the menu is their delicious milkshakes. Just a heads-up: if you order a large, be prepared for a massive portion! We decided to get one for each person in our group, and they turned out to be way too much for us. I probably managed to finish only about a third of mine! Overall, it was a tasty meal and a fun dining experience, perfect for anyone looking to indulge in some classic Chicago eats.
Chicago is such a vibrant and exciting city, and I highly recommend visiting! With its stunning architecture, rich history, and diverse culture, there’s something for everyone to enjoy. I can’t wait to return!
During our trip, we barely scratched the surface of all the activities and attractions the city has to offer. From world-class museums to lively neighborhoods filled with unique shops and restaurants, there’s so much left to explore. I’m already looking forward to my next adventure in this incredible city!
Stay Safe and Start Exploring!!
Sounds amazing! Thanks for your insights!