4 Perfect Days in Chicago
Fred and I ventured up to the Windy City (Chicago) for the Memorial Day Weekend and it was an incredible trip! Although I have traveled there many times for work, it’s not usually more than 15 hours I get to spend in the city. There were some GREAT restaurants we ate at and some fun touristy things we did as well and I am so excited to share them with you all.
You know we also had to vlog our trip, so you can watch our video on my YouTube channel here. Don’t forget to give the video a “thumbs up 👍 “ and also hit that subscribe button if you haven’t already. 😉
Our trip began at the Fort Lauderdale (FLL) airport. We arrived early because Fred had a few work meetings to take before our flight. Thank goodness for the lounge access that our AMEX card gets us, because it was the perfect place to hang before making our way to the gate to board.
Once we arrived in Chicago, I had to take an obligatory photo in the iconic O’Hare terminal. Anyone else immediately think of Home Alone when they see this terminal?
We then hopped on the CTA (the local metro in Chicago) and made our way to our hotel downtown. It was pretty easy to navigate and convenient that the metro station is located right inside O’Hare Airport. We only needed to make one transfer and given that we arrived right at rush hour, it was significantly cheaper than an uber. For both Fred & my tickets it was a grand total of $10 - while the cheapest Uber/Lyft we could get was around $60.
After checking into our hotel, dropping our bags off in the room, we headed straight to dinner. We were both pretty hungry and had our sights set on Ramen for the evening because the temperatures in Chicago we’re quite chilly. Just a short walk from our hotel was Ramen-San where we chose to dine. Not only was their ramen delicious but the portions were HUGE. We also ordered some of their sticky Thai wings which were also extremely tasty!
Our second day started out a bit slow. Fred needed to take a few work meetings so we picked up some pastries & coffee at a coffee shop nearby and enjoyed them in our hotel room. Once he was finished working for the day we ventured out into the city. One of the inclusions of our daily resort fee at our hotel were tickets to the 360 Chicago Observation Deck at the John Hancock Tower. From the 94th floor, you get to enjoy panoramic views of the Windy City. For an additional fee you can also buy tickets to the ‘Tilt” which Fred was brave enough to do. If you want to see more about it - check out our vlog here.
For lunch, we strolled over to Giordano’s to get some of their famous deep dish pizza. I wanted to make note that these pies take approximately 40 minutes to bake, so make sure you’re not in a rush if you plan to eat here. We thoroughly enjoyed our pizza and even though we ordered the smallest size, still had leftovers. (which we of course took back to our hotel to enjoy later that night) 😜
Later that evening I had booked a 7PM spot to go up to “the ledge” at Willis Tower. I was hoping we would get great shots at sunset, but we were a bit early and also disappointed that the windows here were very dirty.
Day 3 began early since we had booked a 10AM Architectural River Boat Tour. We had a quick breakfast in our hotel restaurant and then bundled up to walk over and catch the boat. The tour lasted 75 minutes and gave us some great views of the city. It was also pretty cool to learn about some of the most famous buildings to make up the Chicago skyline.
After the tour ended, we walked over to RPM Seafood where I made a reservation for us to enjoy an appetizer and a cocktail while continuing to take in the beautiful river views and enjoy the incredible, sunny weather!
From there, we walked over to Millennium Park to check out “The Bean” but WOW, was it crowded. Thank goodness I’ve been able to enjoy this cool sculpture on previous trips to Chicago, because the amount of people there was overwhelming and nearly impossible to get any good photos.
Fred did go back at 6AM the next morning and was able to capture some great shots of this iconic Chicago landmark sans the crowd of people.
Dinner that evening was at a Michelin Star Indian Restaurant called Roop. We have actually dined at their sister location in San Francisco a few years ago (which is unfortunately now closed) and loved it so much that we knew we wanted to eat here while in Chicago. Our waiter was amazing and recommended a few of his favorite dishes for us to try. For appetizers we had crab cakes & what we believe was some sort of stuffed naan. For our main courses we tried their butter chicken and lamb shank accompanied with saffron rice and garlic naan. I do not say this often, but that butter chicken was one of the best things I’ve ever eaten in my life. I even had to ask for additional garlic naan to ensure there was no sauce left behind. It was THAT incredible.
Our 4th & final day was jam packed. We began with breakfast at Stan’s Donuts. Fred and I each tried 2 different donuts and they were delicious but very sweet. I’m usually a savory girl when it comes to breakfast, but nonetheless they were still tasty!
One thing Fred was most excited about doing during our trip was going to the Field Museum to see some dinosaurs. This museum is home to “Sue the T-Rex” which is the largest, most complete and best preserved T-Rex specimen ever found. Although I am not a huge dinosaur lover I have to say it was pretty incredible to see Sue.
The museum was also hosting a temporary “Africa Fashion” exhibit which we paid an extra $20 to view. There were over 180 works by artists from 20 different African countries. I loved that there was some traditionally influenced garments as well as modern high fashion looks.
After spending a few hours at the museum we worked up quite an appetite and luckily for us, Chinatown was just a short uber ride away. I had been craving dumplings and knew this would be exactly the place to satisfy my tastebuds. Although we originally wanted to go to Qing Xiang Yuan the wait time was almost 2 hours! So we opted to walk down the street and see what else caught our eye. We ended up at Legend Dumplings and it was pretty good. From there we headed back to our hotel to rest for a bit before dinner.
One place I knew we had to visit before our trip concluded was the Starbucks Reserve Roastery, which was just a few blocks from our hotel. The Chicago location is over 27,000 sq feet, making it the largest Starbucks in the world. It has 5 stories, which each floor offering a different experience. We took the escalator up to the 4th floor to grab one of their signature cocktails. Fred opted for the espresso martini flight and I had the butterfly tea spritz.
Our final meal in Chicago was at none ofter than Portillo’s Hot Dogs’. We had heard a lot about this place and wanted to see what the hype was all about. They are known for 2 items - the Chicago style hot dog and their Italian beef sandwich, so naturally we ordered one of each to try. Although I did enjoy the Chicago dog (sans tomatoes) we felt the Italian Beef sandwich left a lot to be desired. Unfortunately, the bread was extremely soggy and it made the sandwich near impossible to eat. I have to say, I’m glad we tried this place, but I don’t think I can see myself eating there in the future.
Well, the concludes this post about our trip to Chicago. Please let me know in the comments what is your favorite thing about the Windy City. Also, I would greatly appreciate if you subscribed to my blog and shared it with a friend if you enjoy my content.
