NEXT STOP…THE WINDY CITY. After 5 months of being stuck inside and working remotely from home due to COVID-19, I desperately told myself its time to travel.. whether I like it or not, or whether I am comfortable or not. I needed to go somewhere and somewhere fast… I didn’t know where but it was time to go. Suprinsgly Chicago became of interest after I spoke to a close friend who actually went herself. I did a ton of research on places to go, places to stay, and places to eat.. thanks to Instagram I got full live-action on how Chicago was handling the pandemic and enforcing safety protocols.

I and my boyfriend decided to book for 6 days and 5 nights. Again, since I am not a frequent traveler I decided to book our whole trip via Expedia.com. I love how they do bundles deals that offer flights + hotel bookings for a decent price. Another plus is that the more you book you receive traveling points. However, it takes 30 days after your trip for the points to apply.


Our flight was $313.4 roundtrip for 2 passengers. The flight said it would take 2 hours and 33 minutes to get there but we actually got there in 1 hour and 50 minutes. FYI- Yes, I am still afraid of flying but I know how to hide it very well. LOL, my boyfriend on the other hand had a good nap. Maybe someday I will stop being so anxious…someday. Anywho, the flight was pretty quick and within a blink of an eye, we landed into O’Hare at 12:00 pm their time on a bright and very hot Thursday. Upon arrival, we wanted to rent a car but quickly realized that would cost us too much since we were practically almost staying a whole week. Also, since we were staying in downtown Chicago we knew that parking would be hell. We decided to just use Uber during the whole duration of our trip. Now that I think of it I believe it would have better for us to take advantage of their CTA system to save money. The Uber from the airport to our hotel downtown cost us $31.12.

The hotel we booked was located in downtown Chicago on N State Street which is often referred to as their Gold Coast neighborhood. What really attracted me about deciding to book this hotel was their stylish boho design, rooftop pool, and most importantly the amenities and impressive attention to detail. We stood in the Viceory Grand Room which offers a King Bed and Lake View. The total cost of our hotel stay was $1,145. I know you must be thinking OMG ARE YOU CRAZY? YOU SHOULD HAVE DONE AN AIRBNB…but everyone has their preference on how they like to travel and at the moment I am just not a huge fan of Airbnb.

Once we entered the room we were truly impressed. From the crisp white sheets and amazing lake view, we definitely felt like what we paid for was worth it. After checking out the hotel room we decided to step out and grab lunch right next door at a restaurant called Lou Malnati’s. We placed an order for their new lemon pepper wings…( how I wish I could have some right now as I type this) and their famous deep-dish pizza with peppers and chicken sausage. After that, we came back inside to take a nap. We then woke up and got ready to go out but unfortunately, by the time we were done, it was 10 pm and due to COVID-19 and limited hours, most restaurants take their last seating by 9 pm. We then decided to grab some smoothies from a nearby food stand and took a walk around downtown.



The next day we woke up around 8:30 am and got ready to start our day. We went to enjoy breakfast at a nearby spot called The Original PancakeHouse. I absolutely loved their chocolate pancakes and eggs. Once we arrived we were seated pretty quickly and taken care of. Of course, since this is during an unusual era you are required to wear your mask up until you are eating. Once you are done you must wear your mask and pay at the counter. Once we were done we headed back to the hotel rooftop pool. They only allow a certain amount of people at a time. To my surprise, it was not crowded so we got to relax and enjoy the pool for 2 hours. The view at this place was absolutely amazing and it felt great to dip my feet in some water for once.

We then headed back to our room to get ready for a day filled with sightseeing. Our first stop was Millenium Park to visit the infamous Cloud Gate. We were able to snap some pictures with my polaroid. However, they have blocked visitors from touching the “The Bean”. We then walked around the park and walked across the street to visit the Art Institute of Chicago. Tickets were $19 for us both. We were able to get them at a student discounted price. I never really enjoyed the museums until this one. I absolutely became impressed by numerous arts and crafts and historical figures from around the world. To my surprise, I also found a hidden gem from my native country Ghana.

Once we took a full tour, we went to have lunch at Nando’s Peri-Peri… we both got their 1/2 chicken with Portuguese rice. However, this place is known to offer South African cuisine.

We then came back and relaxed a bit and got ready for dinner at 9 pm. We decided to head on over to LuxBar.. their food is amazing and customer service is great too. I got two drinks that’s how good their menu + cocktail was.


It was Saturday and we had a pretty late night so we woke up at 11 am and got ready to head on over to the Shedd Aquarium. Tickets were $90 for us both. I believe this was my first time at an aquarium and again I was pretty amazed by all the different species that live within our ecosystem. Once we arrived we took a tour of all the animals and even enjoyed a 4D version of a 15-minute shark film. I felt like a little girl just for a few hours. Everyone around us had their kids with them and I made a joke to my boyfriend that we would definitely bring our future kids back to visit.

Next, we headed over to the Chicago Riverwalk which offers amazing views of Lake Michigan, the river, and of course Chicago beautiful architecture. We enjoyed lunch at Beat Kitchen: On the Riverwalk. We had tacos and quesadillas and interestingly enough they came in purple. Don’t ask me why… just know it was delicious. Oh, and their drinks almost took me out lol. Shortly after we took a nice tour on the riverwalk with Wendella Tours & Cruises for $78 for both of us. It felt nice feeling the nice breeze as we learned all about the famous buildings in Chicago.

We then headed back to the hotel. It was 6 pm and we were pretty exhausted from all the walking so we decided to plan a night to stay in and watch movies and order dinner with free delivery provided by the hotel.



The next day we rolled around in bed several times before waking up to start our day. We headed over to Tempo Cafe which is a cute little brunch spot offering Cuban vibes with their design. After having some food, we headed to our next stop which was the Sky Deck Tower. To be honest I am absolutely terrified of heights and don’t know why I agreed to come here but you only live life once right. Tickets for both of us were $52. The building has about 103 floors. Due to COVID-19 the lines to enter after you have shown your tickets take a while. We had to use three elevators before getting to THE LEDGE. Once we got there we only had approximately 5 minutes to take photos before we were told we had to leave. Unfortunately, the staff cannot take photos for you with your phone due to safety protocols. However, we were forced to pay for photos provided by them which are pretty expensive.

We then made it back to our hotel to relax.

What I disliked about this trip was because of COVID-19 you had to do things within a certain time frame because of early closing hours. We then got ready to head to dinner at Maple & Ash. We both ordered the filet mignon and fries and when I tell you it was delicious I am not kidding. If you ever have a chance to go to Chi City definitely make this a place to go to. I also loved that they print any cute message for you on a big card menu. Very fun and cute date night I must say!


On our last full day in town, we decided to head on over to visit the malls and take a look around. Right around the hotel is one of their popular malls called 900 North Michigan Shops.Like any mall, we had to wait in a line and sanitize our hands before entering the Gucci, Saks Fifth Ave, and LV store.

After, we headed to one of the very few places I wanted to see….the Navy Pier. I must say this place is a nice area to relax. We walked along the Pier and then headed upstairs to a restaurant called Off Shore Chicago. We took photos, shared some laughs, and then headed back to our hotel.

That evening we had our last dinner at the Tavern on The Rush. Again, I can say all the places we dined at had great service and impeccable food.


On our final day, we enjoyed some breakfast at the Original PancakeHouse once again and headed straight to the airport. Overall, this trip was amazing and I enjoyed every minute of it. I wish I could have stayed longer. Never did I think I would enjoy domestic travel till visiting Chicago. It really made me appreciate the beauty of traveling even more.

One advice I would say is to plan your trip accordingly by having an itinerary of what you will be doing every single day to help give you a guide of how far places are and how much food cost at various places you plan to eat at. Writing out an itinerary definitely helped me budget and plan what outfits I would be bringing. Yes, that’s how organized I am but trust me it makes things so seamless. I know this post was long and If you have reached this part… thank you so much. I hope you enjoyed my travel recap + itinerary. Feel free to message me or email me for any additional questions.


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