I’ll be honest. Chicago was never really on my radar. Whenever I told people I was visiting the United States, they usually assumed I was heading to New York or Los Angeles. A few people suggested Boston, and one family member kept telling me I had to visit Chicago. I’m so glad I listened.
I arrived expecting a nice city with good food and interesting architecture. What I didn’t expect was to completely fall for it within a single day. From beautiful streets and world-famous landmarks to incredible food and some of the friendliest people I’ve met, Chicago surprised me in the best possible way.
If you’re planning a day in Chicago, or are looking for ideas for the perfect day tour in Chicago, this itinerary is exactly how I spent my first day exploring the Windy City.
Starting the Day with Coffee and Something Sweet at Stan’s Donuts
Every good travel day starts with coffee, and Chicago was no exception. I kicked things off at Stan’s Donuts & Coffee, a local favourite that’s famous for its colourful doughnuts and excellent coffee.
One thing I always do when visiting a new café is ask the staff what they recommend instead of automatically ordering the bestseller. More often than not, they know exactly what’s worth trying.
This time I ordered a cold brew with vanilla cold foam alongside a strawberry cream cheese pastry, and it turned out to be the perfect way to start the morning. Sitting outside with a coffee, beautiful weather, and an entire day of exploring ahead of me, I couldn’t think of a better way to begin my first day in Chicago.
Finally Seeing Cloud Gate
My first stop was Millennium Park to see one of Chicago’s most famous landmarks, Cloud Gate. Most people simply call it The Bean, but its official name is Cloud Gate, and seeing it in person is very different from seeing photos online.
Created by British artist Anish Kapoor, the sculpture is made from 168 stainless steel plates that have been seamlessly welded together, creating one enormous mirrored surface weighing around 100 tonnes. It reflects the surrounding skyline, the clouds above, and everyone walking around it, so it never quite looks the same twice.
One of my favourite parts was walking underneath the centre, where the reflections become beautifully distorted. It almost feels like stepping inside a giant mirror. While I was there, I also spotted a couple having their wedding photos taken beneath it, which somehow made the whole place feel even more special.
If it’s your first time visiting and you’re spending 24 hours in Chicago, I genuinely think this is the perfect place to start.
Wandering Through Downtown Chicago
From Millennium Park I simply started walking, and it didn’t take long to realise how incredibly walkable Chicago is. My Uber driver had actually suggested avoiding the train and exploring the city on foot instead, and it ended up being one of the best decisions I made.
Most of the major attractions are only around 10 to 15 minutes apart, making it easy to spend an entire day wandering between neighbourhoods. If you’re planning a day in Chicago, you’ll be surprised how much you can see without relying on public transport.
I always think walking is the best way to get to know a city because you notice the little things. You discover cafés you never planned to visit, admire buildings you would’ve driven straight past, and get a much better feel for the atmosphere. By the end of the day I’d clocked up thousands of steps without even thinking about it.
A Quick Stop at the Chicago Theatre
Next, I made my way to the iconic Chicago Theatre. Opened in 1921, it has welcomed legendary performers including Frank Sinatra, Prince, Dolly Parton, and countless Broadway productions over the years.
Unfortunately, my timing wasn’t ideal because much of the area around the famous marquee was covered in construction work, making it difficult to get the classic photo. It was a little disappointing, but that’s travel sometimes. You don’t always get the postcard-perfect view.
Even so, it’s still worth stopping by, especially in the evening when the famous sign lights up the street.
Choosing Seafood Over Chicago’s Classics at Brown Bag Seafood Co.
Chicago is famous for deep-dish pizza and Italian beef sandwiches, but I ended up doing something completely different.
After scrolling through Google Maps, I found Brown Bag Seafood Co., where the lobster roll looked far too good to ignore. Once seafood enters the conversation, it’s usually game over for me.
It definitely wasn’t cheap at around USD 37 with a bottle of water, but thankfully it was absolutely delicious. The toasted brioche roll was soft and buttery, packed with generous chunks of fresh lobster, and served with perfectly crispy tater tots. It even came with a Swedish Fish lolly, which I’d always wanted to try after hearing Americans talk about them for years. Surprisingly, they tasted almost exactly like Australia’s Red Frogs.
Chicago’s Incredible Architecture
After lunch, I continued wandering through downtown, and this was probably the moment Chicago completely won me over.
I’d heard people describe it as an architectural city before, but I don’t think I fully appreciated what that meant until I saw it myself. Historic buildings sit alongside sleek glass skyscrapers, creating a skyline that somehow feels both classic and modern at the same time.
Chicago is often called the birthplace of the modern skyscraper following the Great Chicago Fire of 1871, when architects began experimenting with steel-frame construction that would go on to influence cities around the world. You can really see that history as you walk around downtown. One street feels steeped in history, while the next feels like it’s been built for the future.
I also loved spotting the elevated “L” trains weaving between buildings overhead. It felt incredibly cinematic, like stepping into one of those American films I’d watched growing up.
Walking Along the Chicago Riverwalk
If you’ve researched top things to do in Chicago, you’ve probably come across the famous architecture river cruise. It’s one of the city’s most popular experiences, and after seeing the skyline for myself, I completely understand why.
I seriously considered booking one, but it was an incredibly hot afternoon, and standing on the deck of a boat in the middle of summer didn’t sound especially appealing.
Instead, I headed down to the Chicago Riverwalk, and honestly, I think it was exactly where I wanted to be. The atmosphere was so relaxed. People were sitting beside the river with drinks, catching up with friends, cycling along the waterfront, or simply enjoying the sunshine. It felt lively without ever feeling overwhelming.
The Chicago River has played an important role in the city’s history, helping transform it into one of America’s great commercial centres, but today it feels like one of the best places to slow down and enjoy the city. If you’re putting together a one-day Chicago itinerary, don’t skip the Riverwalk.
The Cookie Stop I Couldn’t Resist at Levain Bakery
Eventually I dragged myself away from the Riverwalk because I had another important stop to make. Dessert.
One of my favourite cookie shops from New York, Levain Bakery, also has a location in Chicago, and there was absolutely no chance I was leaving without visiting.
I already knew exactly what I wanted. The cookie arrived warm, thick, perfectly gooey in the middle, and every bit as good as I remembered.
Some travel memories come from famous landmarks. Others come from finding an incredible cookie halfway across the world. This was definitely one of those moments.
Bringing Home Something Meaningful
Whenever I travel, I try to avoid buying magnets or keyrings. Instead, I love collecting small pieces of artwork from local artists.
Over the years, they’ve slowly filled the walls of my home, and every single piece reminds me of a different adventure. Looking at them instantly brings back memories of the streets I wandered, the conversations I had, and how I felt in that moment. It’s become one of my favourite travel traditions, and Chicago was no different.
Checking Into Acme Hotel Company Chicago
After a full day exploring, I finally headed back to Acme Hotel Company Chicago, where I was staying during my visit.
The location couldn’t have been better, right in the middle of downtown and within walking distance of almost everything I’d wanted to see. Originally built as the Berkshire Hotel in the 1920s, it’s now a boutique hotel full of colourful artwork, quirky design, and plenty of personality.
After walking around the city all day, I appreciated two things more than anything else: the incredibly comfortable bed and a hot shower. Sometimes that’s all you need after a full day of sightseeing in Chicago.
Chicago Completely Won Me Over
By the end of my first day in Chicago, I realised the city had completely exceeded every expectation I’d arrived with. The architecture was even more impressive than I’d imagined, the food was fantastic, the city felt clean, walkable, and welcoming, and I genuinely couldn’t understand why more people don’t include it on their USA itinerary.
If you only have 24 hours in Chicago, don’t worry. You can still experience so much of what makes this city special, from iconic landmarks like Cloud Gate to the Riverwalk, incredible architecture, and some fantastic places to eat.
And if you’d like to see everything from my first day exploring the Windy City, make sure you check out my Chicago vlog over on YouTube. For more travel guides, hotel reviews, and destination inspiration, you can also explore the rest of the Travel For Phoebe blog. I have a feeling this won’t be my last visit to Chicago.