September 6th – 10th of 2018 My Boyfriend and I visited Chicago for our 5 year anniversary and to see our favorite bands preform at Wrigley field. We had an amazing time exploring the city once we got the hang of it. With a short amount of time in the city, we found ourselves squeezing in something to do every second of our trip in an effort to check every box off.

Our trip didn’t start off in the best way, we missed our flight due to traffic driving to the airport – luckily jetBlue hooked us up with the next flight which ended up working out perfectly… and actually… Bill Murray was on our flight 3 rows in front of us! We flew economy, not first class so, it was pretty damn cool to see him.

We arrived in Chicago around 3pm and got to our AirBnB around 4. Check-in for our BnB was at 3pm. When we got there we learned that the cleaners forgot about our stay. The apartment was not ready for us. This was super frustrating… but we went with the flow and grabbed dinner while our room was being cleaned.

The following day our trip was much better. We actually had a game plan so that we wouldn’t have a crappy day like the previous one.

Day 2 – we spent the beginning of the day walking in the rain attempting to get to our destination. We were not familiar with the public transit system so we were trying our best to use google maps and other maps around the city, but didn’t really have much luck. After our time at the museum of science and industry we made our way to millennium park, the rain had cleared up and the day felt a lot better.
As we walked into millennium park we quickly noticed Monarchs flying all above us – there were SO many and they were so beautiful. We never would’ve expected to see them in a city. After some googling I came across an article written in July of 2018 by the Chicago Tribune and they say that “Monarch butterflies are in their high summer mating and reproductive stages, and Chicago, placed squarely in the center of their migratory range, is enjoying the annual upsurge in sightings of the beloved butterfly.” This was something I never knew and is definitely a perk of living in Chicago – I’d much rather see Monarchs flying around in Central Park or Boston commons than pigeons, but that’s just me.

We did our walk through of Millennium Park on Friday, September 7th. We had to visit Cloud Gate. “Cloud Gate is a public sculpture by Indian-born British artist Sir Anish Kapoor”. If you’re not familiar, it’s basically a extremely large reflective ‘bean’ and a beautiful one at that.

While in Millennium Park we stopped by Crown Fountain. This fountain is an interactive work of public art and video sculpture. While we were there, many families and tourists gathered around, played in the water or sat to enjoy the changing videos on the glass brick towers.

After doing Millennium Park we made our way down South Michigan Avenue and came across North Garden and Dan Kiley Plaza/South Garden at The Art Institute. Both plazas gave a completely different vibe than Millennium Park. I felt tranquility, peace and almost silence in comparison to the street on the other side of the trees separating this space from the traffic. If I lived in Chicago this would probably be a place I’d visit often to just sit and reflect.

The city of Chicago doesn’t seem to mix well with New Englanders when it comes to getting around. Maybe it’s our Rhode Island state of mind. We don’t have a ton of ‘big city’ experience, but we found attractions extremely spread out in comparison to New York and Boston. Did anyone else have the same experience when visiting for the first time?

Located in the center of Grant Park, not too far from Millennium Park, is Buckingham Fountain. The fountain was dedicated in 1927 and inspired by the Latona Fountain at the Palace of Versailles. This fountain was on my ‘Places to Visit’ list, but I must not have done enough research. I had no clue (until just now) that this is one of the largest fountains in the world!

At the end of our adventures in the city on our second day in Chicago we walked to Navy Pier in hope to catch sunset. We walked on the south side and watched the city turn from light to dark. We saw all the lights go on. It was a cloudy/rainy day so we thought the sunset might not be visible. I came close to giving up on it since we saw absolutely no color in the sky.
That was… until we made it to the end of the strip and realized the sun had just gone down. It was only visible on the north side. I was able to snap a couple shots with the pink haze but, I was disappointed that I didn’t think about the location of where the sun was going down. Rookie mistake.

As we walked Navy Pier we saw a ton of groups boarding dinner cruises. Everyone was all dressed up and excited to get on the boat. I’d imagine their view looked was a wonderful twinkling city all night – definitely a beautiful view to have.

We were sure to visit the Shedd Aquarium during our trip to Chicago. The Aquarium was beautiful, especially the jellyfish. We purchased the Chicago CityPASS prior to our arrival in the city and the aquarium was included in this pass. It was completely worth it, I’d definitely recommend it.

On Sunday, the second to last day of our trip in Chicago we visited the SkyDeck Chicago/Willis Tower, also known as the Sears Tower. The Skydeck was included in our CityPASS and it was a breathtaking view – especially during golden hour.
*Note to any photographers planning to visit the SkyDeck during sunset – The Ledge – which seems to be the main attraction when visiting – is exactly the direction where the sunset is. Either have to wait in line and time it perfectly (it was a estimated 45 minute wait when I went) or try 360 Chicago.

Walking around Chicago on a Sunday is not what one would expect. It’s absolutely dead in the city and eerily quiet. All stores were closed. We nearly found a place to eat. Luckily, a noodle restaurant, attached to a hotel was open. It was so dead in the city.  As we were ready to go home we mistakenly left behind our wallet at a bus stop. The bus began to drive away when we realized. Lucky for us it was still there at the stop when we ran back. On a Saturday we wouldn’t have been that lucky.

Once we got back the night before we were ready to leave I made sure I ordered us a Chicago Deep Dish Pizza from Lou Malnati’s. It was delicious as expected.

That was our “Chicago Experience” – check out the photos from the trip.