How to Spend a Long Weekend in Chicago - Part 1

18 December 2019

Chicago, chicago...what a town! I wasn't going to bother writing anything about our time in Chicago as I wanted to just enjoy a lovely pre-Christmas break without the stress of having to sit down and write about it as soon as I got back. However, it's one of my favourite American cities so I felt like I just had to share with you what we did and where we ate & drank in-case you're planning a little trip yourself {hint: you definitely should be}. 


We arrived in Chicago on Friday around lunchtime and as we weren't allowed to check into our hotel until 3pm, we headed out for a little walk to stretch our legs after the 9 hour flight, and get our bearings. We didn't want to plan any of our 'big' activities on Friday just incase our flight was delayed, or we got stuck in line at the airport {you can never be too careful - sometimes US immigration queues can take hours} so we thought we'd head down to the river and do the river walk. The river walk is essentially just a path by the river that they city has designed for pedestrians and cyclists/runners/etc to enjoy the city and it's definitely something that would probably be enjoyed more in the spring and summer when it's not -4°, but it's still definitely worth doing as you really get to take in just how big the city's skyline is - I don't think I've ever seen sky scrapers like it outside of New York. 

After we'd walked up an appetite we headed to Goddess & The Baker, which quickly became our favourite spot. I had the Southwest Salad and let me tell you, it was one of the best salads I've ever eaten. We also shared a gigantic piece of carrot cake to satisfy our sweet tooth. We then headed back to our hotel in the Loop for a little disco nap before heading out to Kingston Mines, a live music venue. Unfortunately we were a little too tired and jet lagged to fully enjoy this but the food was good if you like traditional American fried food!


Saturday was our first full day in the city and the one we'd planned in most of our activities. We were still very jet lagged so we took advantage of being up early and headed down to Millennium Park to visit the iconic 'bean', or Cloudgate as it's officially known. It's definitely something worth visiting early, we were there by 8.30am and there was only a handful of others around so it was great for snapping a few photos...but when we walked past at lunch time the crowds were huge! There's no way you'd be able to get an actual picture of the bean without 300 other people also in the shot. 

After we'd finished at the bean and it started to get a little busier, we headed back to Goddess & The Baker for breakfast, as we'd spied someone having the breakfast burrito the day before and couldn't get the thought of it out of our heads {we're definitely very food motivated 😅}. I had a glitter latte which, while looking amazingly sparkly, actually tasted incredible too, and a breakfast burrito which was most definitely worth the wait. 

After breakfast we headed to the Willis Tower for our Sky Deck & The Ledge Experience, which we purchased on Get Your Guide. We did have to queue to get up to the Sy Deck but the view was amazing at the top...all of the giant sky scrapers look tiny and you realise just how high you've travelled up. The only disappointment was that you only get 60 seconds on 'the ledge' which are the glass boxes which you can stand on and look down at the city {in the picture above}, which isn't a lot when there's three of you who want a photo. Had we of been told this when we purchased the tickets we might have reconsidered the £18 it cost us to get up to the viewing platform, but nevertheless it was a cool experience.

After the Sky Deck, we headed out to a more relaxed 'viewing platform'...Cindy's Rooftop Bar 😅. With a great view of the bean and the whole of Millennium Park, its a great spot for a mid-afternoon cocktail. Then we turned our thoughts to eating...again. We headed out to the West Loop, a cool new area full of exciting restaurants and bars, and went to the Allis at Soho House. Much like all Soho Houses, the Allis was decorated so well and the foot was great, although the brunch menu was a little small. Definitely worth going if you want somewhere 'instagrammable'. 

After lunch, we headed back to the main Loop area and down to the river to hop on the Architecture Tour Boat. Again, this is probably something thats a lot more enjoyable in the summer when it's not freezing, as we did have to sit out in the cold on the water for a good 75 mins 😰. However, I will say that it was definitely worth risking mild frostbite for...we learnt so much about the city and it's buildings, and how the city was built up from scratch following the big Chicago Fire, why it's called the windy city, why it's called the second city, how the city changed the flow of the river, and all about the prohibition era. If you're interested in architecture and history at all, then I'd definitely recommend it. 

After our architecture tour, we headed back to the hotel to defrost and get ready for our night out. For dinner, we made reservations at Siena Tavern and I'm so glad we did - the food and the atmosphere were both incredible. If you're planning on visiting, definitely make a reservation as the entire restaurant and bar were packed, and have either the truffle and sage gnocchi or the brick chicken. After dinner, we headed to a friend's flat for drinks with a view, and what a view it was 😍. If you're looking for a similar view of the city at night {and I definitely recommend you do}, you can head over to the bar on the 95th floor of the John Hancock tower for a similar view! 

I quickly realised when I started typing this post that it would be quite a long one, and keen to not miss out any of the details, I thought it would be best to split the post into two look out for Part 2 coming shortly! 

xo Becky 

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