Lifestyle // Chicago Travel Diary #2 – Scaling Skyscrapers,Tequila &Tacos and Understanding Architecture

July 22, 2016

Willis Tower, Navy Pier, Cinco de Mayo, Hancock Tower & Architectual Boat Tour

On Friday I posted the first of my three Chicago Travel Diaries – detailing my exploration of Millennium Park, the Lakefront Trail, Lincoln Park Zoo and a hell of a lot of shopping (go check that out here if you haven’t already). In today’s travel diary I scale two skyscrapers, visit Chicago’s number one tourist attraction Navy Pier, celebrate Cinco de Mayo, take an architectural boat tour, explore the beautiful Chicago Cultural Centre and get ready for a weekend of partying! 

DAY 3 – Thursday 5th May

Feeling a little bit guilty about my afternoon spent shopping yesterday I decided to ramp up the tourist attractions on Thursday. I started the day by going to the top of Willis Tower to take in the beautiful views across the city. The Willis Tower is a really innovative design, made up of nine different height spheres, which used to belong to the Sears brothers. It was amazing to see out across the city and its incredible to see how big Lake Michigan really is – you can’t see across to the other side, it’s like an ocean! Willis Tower is famous for its glass ledges that hang out over the side of the building 103 floors up and I couldn’t resist making the most of the photo opportunities! (You can see the glass ledges in the photo below! Pretty high!!!) My top tip is to head straight to the ledge manned by the official photographer. The queue wasn’t long at all and it meant that you get the entire ledge / box to yourself, whilst at the unmanned ones people were being told to share, so three groups of people were standing there at the same time. This means you get to take your time a bit, not have people you don’t know in your pictures and also allows idiots like me to get down on the floor and make a spectacle of themselves! There’s always one….! The professional photographer was also more than happy to take photos of me on my own camera as well as his, so if you decide not to purchase your official picture (of which there’s no obligation) you still have your own images to enjoy.

I then decided to walk down to Navy Pier – voted Chicago’s top tourist attraction. I had been down to Navy Pier last time I was in town eight years ago, and it was very much like Brighton Pier – fun fair rides, arcade games and restaurants. This time however absolutely nothing was open! Fair enough it was out of season, but there was literally nothing to do! I did have a nice walk around though and it was beautifully bright and sunny with hardly a cloud in the sky. I wouldn’t bother to come back to this part of town again, as the attractions and restaurants are very mainstream and I think I’d much rather explore a different neighbourhood with a bit more character that’s more unique to Chicago.

After about an hour’s strolling and people watching I headed back to the city. I had an hour to kill before meeting Sarah from work so I took a leisurely walk, enjoying the views and beautiful buildings, and getting a bit too excited when spotting the sign marking the official start of Route 66. (And let’s not talk about the actual squeal that escaped me when I spotted the Honorary Hugh M. Hefner Way sign! What can I say, I’m a massive Girls Next Door fan!) I eventually ended up back in Millennium Park, seeing my beloved Bean and watching the Crown Fountain – which features two huge columns which have people’s moving faces projected onto them. They’re really striking and it’s very easy to while away time watching the videos move, and open their mouths releasing torrents of water.

By the time Sarah had finished work I was well ready to go and celebrate Cinco de Mayo, which in America is largely about the celebration of Mexican culture.  We headed to Latinicity, a type of food hall where you’re given a blank payment card to use and can then swipe this through at the various food stations and bars and then pay at the end. We had some amazing tacos, a ton of tortilla chips and guacamole and of course a good few celebratory cocktails! Guac and roll! 

DAY 4 – Friday 6th May

I’m a huge architecture fan so was desperate to take the Chicago Architecture Foundation River Cruise down the Chicago River to learn more about the incredible buildings that line the banks and the the growth and history of the city. It was a great trip – really relaxing and a nice way to see everything if you’re just after a boat trip, but also really informative and interesting if you do have an interest and light knowledge of architecture. I particularly loved hearing about how the buildings are built with the body of the river in mind, so some are designed to echo the curves of the river and have mirrored cladding to reflect the colour of the water, blending in. Other buildings have bridges built into their aesthetic to echo the fact that Chicago is the drawbridge capital of the world, with 43 movable bridges. I did a boat trip on my last visit to Chicago but would definitely recommend the official Chicago Architecture Foundation tour if you’re interested in learning more than you would one of the other simple sightseeing tours.

I then decided to head up Hancock Tower, where another large viewing platform – 360 Chicago –  is open and this one has a bar – hurrah! It’s five o’clock somewhere right?! I bought a ticket which included a cocktail that worked at only $5 (it would be silly not to!). At the top I ordered myself an Amaretto Sour and looked out over the city from this new perspective. The view is largely the same as from Willis Tower, but with less buildings and more lake, but I think the experience was much nicer at Willis Tower, despite the delicious cocktail addition (and I think you probably only need to do one or the other). The view at Willis Tower is more striking as you get to view the buildings of the city on three sides rather than just two and the observation deck is a lot bigger. I also really enjoyed going out on the glass ledge at Willis Tower, which you can’t do at Hancock Tower, though they do have “The Tilt”, whereby you pay extra to stand on a mechanism which tilts out over the streets, giving a dramatic look downwards. I have to say though it looked pretty tame and a bit gimmicky and this seemed to be the same sentiment of those I spoke to who had “braved The Tilt”, so I’m glad I spent my extra cash on a cocktail instead! 

I was due to meet Sarah for a late lunch shortly so I headed back up to The Loop and stopped off at the Chicago Cultural Centre (basically because I needed the loo!) but was pleasantly surprised to find that it was absolutely stunning inside! It’s really extravagantly decorated with marble and beautiful tiling, with quotes from famous authors adorning the walls. The second floor is also home to a huge beautiful domed Tiffany ceiling which is just gorgeous and well worth a pit stop. 

I’m going to stop this travel diary here and pick up Friday afternoon in the final instalment, which sees me exploring a LOT of rooftop bars, eating ALL THE FOOD (deep dish pizza anyone?!) and heading to a baseball game, as the weekend rolls in and the party starts! 

Which is your favourite city architecturally?

Bloglovin // Twitter // Instagram

Chicago Travel Diary #1 – Adventure, Art & Animals

1 comments so far.

One response to “Lifestyle // Chicago Travel Diary #2 – Scaling Skyscrapers,Tequila &Tacos and Understanding Architecture”

  1. Pam Scalfi says:

    the views are just so mind blowing. gorgeous! :DPam xo/ Pam Scalfi♥

Leave a Reply

Your email address will not be published. Required fields are marked *

I’m Emma – or Emsypickle!


I live in Brixton in London. I eat out far too much, am always planning my next trip and have a borderline unhealthy obsession with Harry Potter.

Never miss a post

Enter your email address to receive notifications of new posts by email.

Join 4,022 other subscribers