How to Spend One Day in Chicago (+Photos)

Ah, the Windy City. One of the most vibrant metropolises in the U.S., Chicago is the undisputed star of the Midwest, and it has stunning architecture, an incredible music scene, and world-class culinary offerings to prove it.

Somewhere as diverse and wide-ranging as Chicago takes quite a bit of time to truly unravel, but that doesn’t mean you can’t squeeze in a slew of the city’s can’t-miss attractions into one action-packed day. In fact, having had a little over 24 hours in Chicago recently, I opted to do just that.

When you’re trying to work your way around a new city within a limited timeframe, you’ll need to plan your day around the spots you absolutely cannot miss. Needless to say, this can be somewhat of an ambitious task somewhere as expansive and enthralling as Chicago!

In the hopes of making your visit as smooth and seamless as possible, I’ve detailed every aspect of my one-day quest around Chicago, including an overview of how to navigate the City by the Lake.

Getting Around Chicago


If there’s one thing the States is certainly not known for, it’s public transport. However, Chicago is among the easiest parts of the country to explore without a car, which already takes a whole lot of stress out of getting around.

Chances are, you’ll be staying within the central Chicago Loop or the neighboring districts of the West Loop, South Loop, River North, or Lincoln Park. All of these areas are well-connected by subway lines, bus routes, or a combination of both.

Thankfully, figuring out the transport here is super simple. When it comes to taking the bus, all you need to do is pay the driver in cash or use contactless payment as you board.

Catching the subway is straightforward as the ticket machines also accept cash or cards. I only found out as I was leaving that you can purchase a Ventra card at a subway station or select convenience stores and add a 1-day pass.

Both cost $5 each, but the fee for the Ventra card can be used as credit if you register it.

The closer you move toward the centre, the more opportunities you have to explore the city on foot. However, as walkable as the downtown area is, Chicago is spread out over numerous districts, so you’ll probably need to make use of public transit at some point.

Admire the Architecture Along the Magnificent Mile and Riverwalk

Magnificent Mile

Having heard nothing but gushing reviews of Chicago’s remarkable architecture, my first early morning port of call was a leisurely wander along the Magnificent Mile and down toward the Riverwalk.

Stretching out over 13 blocks, the Magnificent Mile boasts a mix of luxury stores, hotels, bars, and restaurants, most of which are set in the most beautiful, eye-catching buildings. Start your stroll at the John Hancock Center and make your way down to the DuSable drawbridge at the riverside.

There are dozens of spots to keep an eye out for along the way, but some of the most captivating include the Chicago Water Tower, the Wrigley Building, and my personal favourite, the Gothic-style Tribune Tower. Along the way, why not pop into the Starbucks Reserve Roastery? It’s only the largest Starbucks location on the planet!

As you approach the Chicago River, continue onto the riverside boardwalk, which I thought was among the most photogenic spots in town. Here, you’ll find the soaring Trump Tower, the inspiration behind Dubai’s Burj Khalifa, and the gorgeous Jewelers Building.

Take a Boat Tour Down the Chicago River

Chicago Boat Tour

While you’re in the area, I highly recommend you embark on a boat tour along the Chicago River.

A quintessential Windy City experience, sailing down the river really highlights how extraordinary Chicago is, and the architecture somehow looks even better from the water. Many of the most popular cruises last for 90 minutes, but with just one day in Chicago, it’s best to stick to the shorter 45-minute alternative. For the same reason, booking your excursion online ahead of time will allow you to stay on schedule.


Double-check that your boat departs from the area surrounding the DuSable Bridge. A ton of companies run from here, but picking one that starts and finishes elsewhere can be quite a nuisance.

Not only will you have the opportunity to gaze at everything from the legendary Willis Tower, Chicago’s tallest building, to the shimmering Lake Michigan, but you’ll also get some insight into the city’s history from your guide. Had I not made time for this tour, I’d have left with very little knowledge of Chicago’s fascinating past and the architects who left their mark on the city.

With any luck, things will wrap up back near the bridge, and you’ll be within easy reach of your next stop.

Marvel at Cloud Gate

The Bean

At the top of my Chicago to-do list was a visit to Millenium Park to catch a glimpse of The Bean, arguably the most recognizable landmark in town. Also known by its official name, Cloud Gate, this bean-shaped art installation is simply extraordinary and has established itself as a symbol of Chicago ever since it was unveiled in 2004.

Millenium Park is a mere 10-minute walk from the DuSable Bridge, so it nestled itself nicely into my jam-packed morning in the city.

Unfortunately for me, the main plaza around Cloud Gate was out-of-bounds for visitors during my visit. This meant I could admire it for as long as I pleased, but I couldn’t capture the iconic snap standing alongside the perfectly polished masterpiece.

While you’re in the area, stop by the Jay Pritzker Pavilion, an outdoor concert hall built in a distinctive, deconstructivist style. Even when there aren’t any events in action, you’ll be blown away by the striking design. If you have time to spare, walk south into Grant Park and pay a visit to the dazzling Buckingham Fountain, among the biggest in the world.

Spend an Afternoon at Navy Pier

Navy Pier

Make your way back to Cloud Gate and walk to the bus stop behind the Millennium Monument to hop on the bus to Navy Pier. Look out for the 124 route, which will have you at the entrance to the pier within 15 minutes.

As the focal point of all of Chicago’s lakeside action, Navy Pier is the kind of place where you could easily spend all day. With just one day in Chicago, an afternoon will have to suffice.

The terminal building stretches almost the entire length of the pier and is packed with restaurants, souvenir shops, and the most fantastic rooftop bar in the city. Provided the weather’s on your side (it was much too chilly during my visit), a drink here overlooking the skyline is a brilliant addition to any trip to Navy Pier.

If you’re travelling with youngsters, the Children’s Museum here is another great option, while the towering Centennial Wheel is a favourite amongst both big and little kids.

Before you move on to your next hotspot, take a few minutes to roam around the edge of the pier and soak up the views of the glistening Lake Michigan and endless array of skyscrapers.

Amble Around Lincoln Park

Lincoln Park

Before dark, explore the northern pocket of Chicago by strolling back towards the Magnificent Mile to jump on the 151 bus to Lincoln Park.

Far from the hustle and bustle of downtown, Lincoln Park was a breath of fresh air, and its distance from the central clutch of high-rises afforded me the opportunity to appreciate the beauty of the city from an entirely new perspective.

Lincoln Park Conservatory

I’d booked into the Lincoln Park Conservatory, a magical botanical garden, ahead of time, so I ensured I arrived in time for my time slot. Entry here is completely free of charge, but advance bookings are mandatory, so be sure to bear this in mind if you plan to visit.

Walking through the Conservatory and taking in the sights and smells of the fragrant flowers and tropical plants would easily distract you from the brisk winter conditions outside. That being said, it’s sure to be just as impressive at any time of year.

If you’re visiting during the warmer months, you might also be keen to check out the nearby Lincoln Park Zoo. Much like the botanical garden, there’s no admission fee, though reservations aren’t necessary here.

Sample Chicago’s Deep-dish Pizza

Deep-dish Pizza

Chicago has an exceptional gastronomic scene, but there’s one particular dish that steals the limelight every time. Recognized worldwide as a Chicago classic, deep-dish pizzas deserve their own spot on any Chi-town must-do list.

Chicago-style pizza was born thanks to the innovation of Italian Americans during the first half of the 20th century, eventually evolving into a culinary favourite among locals.

You won’t run into any difficulty in locating some top-notch deep-dish pizzerias, but the likes of Lou Malnati’s and Giordano’s are two names to look out for. Both have locations in the wider Lincoln Park neighbourhood, so either will be within walking distance from the Conservatory.

After some deliberation, I settled on Giordano’s and decided to order a small, deep-dish pizza for myself. You might be thinking that this doesn’t sound like a whole lot, but the huge volume of cheese, rich tomato sauce, and thick, pie-like crust meant I had to get most of my meal in a to-go box.

Given how filling this dish is, a small size will easily keep two people satisfied, though even the personal pizza seemed like a challenge for one person to polish off!

If you’re a first-timer, stick to the traditional option with minimal toppings and save the pepperoni and vegetable-filled creations for your next visit.

Leave a Reply

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