Welcome back to a brand spankin’ new travel post. One I’m so excited to be writing as it’s all about (hands down) one of my favourite trips ever. I still have a huge grin on my face thinking about what a ball we had. It was my second trip to the US of A, and exceeded all of my expectations. I thought New York was a dream come true. Chicago even exceeded that.  

I’m currently writing this at 8.10am on a Monday morning, dressing gown on and mint tea in hand because the summer in the UK apparently lasted all of 3 days. So bare with me if it’s a long post. When I’m tucked up inside with no obligation to go out, I could sit here and write travel content all day long.  

I’m also making myself occupied and not get saddened by the fact that summer seems to have come and gone. And it’s not even May. 

I was so sure it would stay longer than 72 hours, the summer wardrobe came out and everything. I had a whole wardrobe refresh, alongside the blog refresh, and I thought it was about time to put the winter dressing gown away and swap the teas for iced coffees but I got too ahead of myself.  

The long weekend in Chicago sure got me wishing for warmer days itself. The weather forecast whilst we were there was like nothing I’ve seen before. Our second and last day saw us in our t-shirts walking down the Gold Coast like it was 40 degrees and the for the third, we were wrapped up in all the layers we could manage ready to battle the snow storm. My nude faux fur aviator was my saviour for this trip. It was light enough to wear over a t-shirt for those truly gorgeous sunny days, and big enough to pack under all the layers for the snowy Sunday.  

Chicago weather seems to be even more confused than the UK’s, but just like the UK, the sunny days were a delight. It was surreal to have experienced snow yet again for our second trip to America. They really make us look stupid as they clear masses of snow away, no problem. Whereas us in the UK go into meltdown if we see an inch.  

So, let’s get into the good stuff shall we. All the not-so-prepped-but-good-snippets from our trip can be found in my Chicago Instagram highlights if you fancy giving that a look for anything I may miss in my rambles.  

Where to stay: 

We stayed in The Drake, a Hilton Hotel and it couldn’t have been more perfect. It was old wordy in a classy chic vintage way. It is located downtown on lakeside of Michigan Avenue and right at the top of Magnificent Mile, overlooking the lake. With beautiful views, bigger than life beds, a grand entrance and incredible grand interiors, this was like something out of a movie. 10/10 for location and space for feeling right at home. It is a central point for all of the best activities to.  

Where to eat: 

If you know me by now or watch my Instagram stories, you know I love food. So be it, I did all the research for the best Chicago eats and this is what I found and devoured.  

Katana*: hands down the best Japanese food I’ve ever eaten. This is a Teppanyaki & sushi restaurant with all the feel good, fresh and locally sourced Asian food your heart could desire. Try the Katana Roll. SO DELICIOUS. 

Kanela*: a homely brunch spot in Old Town to feel in with the locals. No tourists seemed to be in here, it was packed of Chicagoans. A good sign if you ask me as it was clear from the get go that this was a neighbourhood hot spot. Leave room for their Monkey Bread, it was soon wolfed down after the first taste. It was a cinnamon roll dream.  

Barrio*: if you love a nacho, fajita or damn good margarita, Barrio is a must. Its relaxed atmosphere is great for an end of the day wind down. Paired with a few of their signature margaritas, good company and nachos, you won’t leave feeling empty.  

The Kitchen*: this is the place to go in a snow storm I tell ya. It’s warm, homely and so relaxing. We spent a couple of hours here and took advantage of their brunch cocktails. The Rose Spritz was ordered more than once, let’s put it that way. It was my first time trying Shakshuka and it didn’t disappoint. PURE YUM-NESS. 

Siena Tavern*: wherever we go, we’ll end up going to an Italian. Whether it’s for good pizza, wine or the vibe, we will find one if it’s the last thing we do. Siena Tavern was outstanding for value and food. The red wine paired with pizza and fresh fish was delicious. A definite recommendation for a relaxed late-night dinner.  

Lunchroom @ Space 519*: if you love food AND interiors, this is the spot. This was probably my favourite find of the trip. It was a 5-minute walk from our hotel and our last meal of the trip. If we were to stay longer, I would’ve been back. The food is all feel-good, fresh, homemade with a vegetable forward California laid back vibe. Aka, utter perfection and my style down to a T. It’s an all-day buy generic ativan café so I’d recommend for breakfast, brunch or lunch. 

Where to visit: 

Museum of Contemporary Art – a super chilled modern art museum located just off of Magnificent Mile and also around the corner from our hotel. The exhibitions change all the time. I do love a good modern art museum.  

Skydeck at the Willis Tower* – a must see/do if you visit Chicago. Even if you hate heights, please assure me you’ll try it. The Willis Tower (also known as the Sears Tower) is a 110-story/1,450 feet skyscraper. It has a sky ledge where you can walk on glass and look down under your feet to the city below. It’s a real adrenaline rush pinch me moment. 10/10 recommend. 

360 Chicago* – another popular skyscraper in Chicago within the John Hancock building. This isn’t so big as the Willis Tower, 96-floors, but the views and experience is on par. They have a Tilt experience where you are literally tilted 60 degrees out whilst being 1000ft in the air. It’s just a pane of glass between you and the city. Craziness. 

Andy’s Jazz Bar – If you like good music and damn good G&T, head to Andy’s Jazz Bar. You can’t go wrong with live music, especially jazz in a city that LOVES it. In the evening there in an entrance fee, which gives back to the act performing and it’s so worth the 10 bucks.  

The Bean – a public sculpture and centrepiece of the AT&T Plaza at Millennium Park in the Loop community area of Chicago. Such a cool piece of art in the middle of the city. Make sure you take a picture of your reflection, it’s a good laugh. 

Historic Route 66 Begins sign – I had no idea that the famous Route 66 started in Chicago, did you? Was pretty cool to see the sign and experience the beginning of the route.  

Lincoln Park Zoo & Conservatory – if you’ve seen Madagascar you’ll already know of this zoo. I met Alex the Lion and my favourite penguins here and had the time of my life.  

They clearly weren’t the actual characters from the film, but were pretty close and I got pretty damn excited about it. The zoo and conservatory are free to enter and, in my opinion, I’d make an afternoon of it and walk down the Gold Coast after, weather and time permitting. This coastline leads you right back to Magnificent Mile. The mile is a definite must do, even if you don’t like to shop and just fancy a walk down to get to another destination. You’ll always need to pass by it to get to somewhere else in the city. You kinda can’t miss it. If you don’t fancy shopping but wanna treat yourself, pop your head into Dylan’s Candy Bar and live your true Willy Wonka dream, sweet style. 

I’d 100% recommend walking down the Gold Coast as it’s a whole experience in itself. On one side you’ve got the city skyline and on the other, blue waters of Lake Michigan and golden sand. My head was confused but heart content. The beach lover within me couldn’t believe her luck.  

What I wore: 

Sun, snow, wind, rain. You name it, we had it. For once, I’d packed accordingly. Layers were the right way to go for this trip and my number one recommendation for a spring city trip here would be a big jacket. I relied on my Missguided Nude Faux Fur Aviator Jacket every day. It was perfect to throw over a tee and also the battle the snow. The colour goes with everything and is so cosy to take you from day to night.  

Evening jackets aren’t a priority but a light jacket is perfect if you’re only heading out for a dinner or drinks if you fancy an outfit change. The light trench is in this season, so I took my new fave from New Look.  

For day time it was very much laid back and relaxed, whilst needing to be comfortable. So, packing the right footwear was a priority. One day we walked 35,000 steps – yes you knew it before I said it, a few gins were needed that evening. I took my trusty Hi Converse and Yeezy’s. The evenings saw me in black court heels and what a good pack that was. Black court heels are so effortless and go with everything.  

Day-to-day wear:  

Evening wear: 

Would I recommend Chicago? 

11/10 YES. It is a city so different to anywhere else I’ve been. The flight isn’t too bad from London (around 8 hours) and I would go back in a heartbeat. They people of Chicago are unbelievably friendly, it’s a very chilled city with something to fulfil everyone’s city break needs. Good food, culture, sights, shops and some of the coolest towers I’ve ever been in. No wonder it’s known for its tall buildings.  

You can also keep costs down in a place like Chicago with lots of free activities and also budget-friendly eats. You can’t go short of good food in Chicago, let me tell you that. Every meal is satisfying and it was good to eat in true American style when we were there. Let’s just say, I wasn’t hangry and was very satisfying full for the whole trip – aka, my favourite way to be.

Chicago, I’ll be back.  

M x  

This post contains gifted visits, marked with an asterisk. All reviews and opinions are my own *