Day 1 Itinerary

We woke up at 6am to check out the Cloud Gate Sculpture, more widely known as “The Bean”, at Millennium Park to avoid all the crowds and get our photos. It was actually quite nice and peaceful – there were a few photographers present taking photos and there was an outdoor yoga class nearby at the Amphitheater but otherwise, the park was pretty empty! When we had gone back in the afternoon to get some reflection photos with the crowd, it was so packed that it was hard to go under the sculpture due to the sheer amount of people. 

Afterwards, we went to Goddess and the Baker for some breakfast. I ordered their almond croissant and their key lime pie bar, both of which were delicious. And yes, I know, it’s a little too early to start eating too much sugar but I can’t turn down key lime pie! Anyways, it’s a really cute bakery and a perfect place to people-watch.

Since we visited the Bean so early in the morning, we had so much time to kill before our visit to Willis Tower. We ended up walking around after breakfast, stopping by the Chase Tower Plaza to see the Marc Chagall “The Four Seasons” mosaic on our way to the Chicago Cultural Center. There are also plenty of benches there so it’s a nice stop to rest if you take snacks and coffee to go!

One site I really recommend adding to the sightseeing list that most tend to overlook is the Chicago Cultural Center. Why is it a place to visit? It has a massive stained-glass ceiling and is known to be the largest Tiffany dome in existence. Originally designed for the Chicago Public Library, it was acquired by the Cultural Center in 1986. The entrance to the center is free to visitors and they open at 10am so it was nice to be able to go inside as soon as they opened to avoid any crowds!

DID YOU KNOW?
The Tiffany dome alone is currently valued at around $35,000,000!!!

We managed to leave the Cultural Center in time to walk over to Willis Tower for our Skydeck visit! I highly recommend purchasing the Combo ticket in advance to save on costs. Coming from New York, most of our museums are Pay-As-You-Wish (Update: The museums are now free for NYC residents while visitors must pay a fee) so it’s definitely more cost-effective to combine entrance prices as often as possible. We wanted to visit both the Skydeck at Willis Tower and the Art Institute of Chicago so we purchased the combo ticket online in advance to avoid waiting in queues.

TIP:
Skydeck Entrance Fee: $24
Skydeck + Art Institute Combo Ticket: $47
You can purchase tickets online in advance here

I have a fear of heights so going up this Tower is definitely not for the faint of heart. I remember visiting this tower when I was in high school (back then it was called the Sears Tower) but I didn’t recall being quite so terrified then. I suppose the difference now is that there are a few “ledges” that you can step on where the entire container is transparent – there are site photographers there who take photos for you but you can also ask them to take photos of you with your mobiles as well if you don’t want to pay for them. Stepping onto the ledge was quite an experience so just power through the fears for that photo!

Once we finished our visit to the Skydeck, it was time for lunch! We were unable to get reservations for The Girl and the Goat for this particular trip since it was planned last-minute but we were able to get brunch at its sister restaurant The Little Goat Diner! I tried their iced latte with goat milk and…I have to say – goat milk is definitely not for me. And it just goes to show that just because you enjoy goat cheese does not necessarily mean you will enjoy goat milk. But I was at least able to say that I tried and just cross it off my list as a novelty experience!

Their breakfast is served all day – which is perfect for brunch lovers. While my friend and I normally share our dishes, we both were craving the same meal so we each ordered “This Little Piggy Went to China”.

One of our last stops of the day was the Restoration Hardware Chicago. Mainly a high-end furniture store, RH Chicago actually has a really lovely café inside and a rooftop where you can just rest, have some tea, and chat. We explored the different furnitures rooms, looked at textiles, took a breather on the rooftop, and ended our afternoon at the café with some tea and cookies! While we were walking around the city, we constantly smelled chocolate chip cookies so it really hit a craving.

We did end up at the Purple Pig for dinner but we were honestly way too full from the day to enjoy a full meal. The restaurant does not accept reservations and wait times tend to exceed two hours. We waited roughly an hour and a half so it was a bit disappointing that we weren’t able to eat as much to really experience the dining atmosphere. It doesn’t help that it is an incredibly tourist spot so there is a lot of foot traffic in the area. One of the snacks we ended up eating was the pork liver and bacon paté on toast. The Purple Pig is a popular spot but I feel like Chicago has better restaurants to offer than here to be quite honest.