Michelle Cacija

Welcome to Chicago, the Windy City — where towering skyscrapers kiss the clouds, the Chicago River winds through a city bursting with life, and every street tells a story. Stand before the mesmerizing Chicago Bean, its mirrored surface reflecting the city’s heartbeat. Indulge in the legendary deep-dish pizza, a cheesy, golden delight (love it or hate it but you have to try it!). Feel the cool breeze as you wander the riverwalk, surrounded by skyscrapers that shape the city’s iconic skyline. Ready to dive into the heart of Chicago? Servus and welcome to my Chicago Blog!

As always, I want to remind you, that this blog isn’t perfect because everyone travels differently, and all trips involve changes of plans. I want to let you know that everything on this website has been experienced, photographed, and written by me. Since I finance all of my travel expenses on my own, the stories and opinions given are truly my own. If you’re interested in seeing more travel pictures or videos, feel free to check out my Instagram @michellecacija or my Tik Tok @michellecacija.

Index

1. The Basics about Chicago
2. Things you need to be aware of
3. Medical insurance
4. Top 10 Things to do
5. Summary of activities
6. Summary of where to eat
7. Other North Amerian Blogs

The Basics about Chicago

When to visit

The best time to visit Chicago is in the spring (April to May) and fall (September to October). During these months, temperatures are usually pleasant, making them ideal for long walks along Lake Michigan or sightseeing in the city. Fall offers breathtaking foliage, but due to the city’s famous winds— hence the nickname “Windy City” — it can also be quite chilly. Be sure to pack a warm sweater. Summers can often exceed 30°C (86°F), while winters are very cold, frequently dropping well below freezing. On my first visit to Chicago in early September, the weather was good for exploring the city since it was mostly warm temperatures but sometimes a bit windy.

Time Period

To fully experience Chicago, I recommend staying for at least three to four days. This will give you enough time to see the city’s major sights. You’ll also have time to enjoy the famous deep-dish pizza and take an boat or kajak tour along the Chicago River. If you have more time, staying five or more days will allow you to explore even more of the city.

Getting there

Chicago is well connected to international travel via O’Hare International Airport (ORD), one of the largest airports in the U.S. and a major hub for United Airlines. Alternatively, Midway International Airport (MDW) primarily serves domestic flights. From O’Hare, the Blue Line of the Chicago Transit Authority (CTA) conveniently takes you to downtown Chicago in about 45 minutes.

Where to stay

I recommend booking accommodation in downtown Chicago, particularly in The Loop or River North. While hotels in these areas can be pricey, the convenience of being close to major attractions and restaurants makes it worthwhile. If you prefer a quieter setting, consider staying in Lincoln Park or West Loop, which also offer great accommodation options.

Getting around

Chicago’s public transportation system, operated by the Chicago Transit Authority (CTA), includes buses and the famous “L” train (subway), which runs both above and below ground, offering fantastic views of the city. In addition to public transport, Uber and Lyft are widely available for longer distances. For a more scenic way to explore the city, renting a bike or strolling along the Lakefront Trail is a great option.

What to pack

Your packing list depends on the season you’re coming for. In spring and fall, a light jacket and a sweater or jumper are essential since mornings and evenings can be chilly. These seasons are also often quite windy, so layering is a good idea. Summer calls for light clothing, sunscreen, and sunglasses, as temperatures frequently exceed 30°C (86°F). In winter, a warm coat, hat, scarf, and gloves are necessary, as temperatures can drop below -10°C (14°F). Comfortable walking shoes are a must year-round, as Chicago is a city best explored on foot.

Additionaly, consider bringing your own little medication bag, including Band-Aids, pain relief tablets, sleeping tablets or spray, bug spray, aftersun, etc. You never know what you might need it for, and you might feel more comfortable using medication from home rather than in a country where you don’t know the ingredients and languages. If you’re coming from outside Australia, don’t forget to bring a Type I power adapter.

Cost of traveling

Like most major American cities, Chicago isn’t particularly cheap. Hotels in the city center can be expensive, and dining out often comes at a high price. However, there are ways to save money, such as purchasing a CTA pass for public transportation or visiting free attractions like Millennium Park and Lincoln Park Zoo. If you’re a foodie, indulging in a deep-dish pizza or a classic Chicago steakhouse meal is a must — sometimes, you just have to treat yourself!

Things you need to be aware of

Water in Chicago. In general Chicago’s tap water is safe to drink and meets federal and state quality standards. The biggest source is from Lake Michigan and undergoes rigorous testing and filtration. However, older buildings may have lead pipes, so it’s a good idea to let the water run for a few seconds before drinking.

Toilet situation. Finding public restrooms in Chicago can be a bit challenging — at least that’s what I experienced when I visited in 2022. While major attractions, museums, and parks like Millennium Park have clean facilities, standalone public toilets are rare. Many cafés and restaurants require a purchase to use their restrooms, so planning ahead is key. Always use one when you got the chance!

Tipping is a common practice in the United States. It’s customary to tip 15-20% at restaurants. In bars and coffee shops, leaving a small tip is also appreciated. For taxis and rideshare services like Uber, tipping 10-20% of the fare is standard. Hotel staff and tour guides also appreciate tips for their services.

The Currency used is the United States Dollar (USD). In Chicago, both cash and credit/debit cards are widely accepted, and cards are often preferred for convenience. Mobile payment methods like Apple Pay and Google Pay are also commonly used. However, having cash on hand is always useful for small purchases, tipping, and certain vendors, like food trucks and street markets. ATMs are plentiful throughout the city, but be aware of potential withdrawal fees.

Medical insurance

I highly recommend getting travel medical insurance while you’re traveling. Hopefully, you’ll never need it, but it’s always better to be safe than sorry. SafetyWing offers two flexible plans tailored to your travel needs — whether you’re a short-term adventurer or a long-term expat, you’ll have reliable coverage anywhere in the world.

SafetyWing is especially great for remote workers and digital nomads, offering continuous global coverage even if you’re hopping between countries. Of course, it’s also a solid option for frequent travelers or those constantly on the go. But if you’re only traveling occasionally or just for a short holiday now and then, there might be better-suited alternatives.

Top 10 Things to do

1. Visiting the iconic Chicago Bean

Right in the heart of Chicago, Millennium Park is a must-visit, blending nature, art, and architecture across 99,000 square meters. It’s home to iconic attractions like the interactive Crown Fountain, the lush Lurie Garden, and the Jay Pritzker Pavilion, where summer events and concerts fill the air.

But let’s be honest — most people come here for Cloud Gate, better known as The Bean. Designed by Anish Kapoor, its mirror-like surface perfectly reflects the Chicago skyline, making it one of the city’s most photographed landmarks. Whether by day or night, you’ll always find crowds admiring and snapping pictures of this futuristic sculpture.

Millennium Park sits on the edge of the larger Grant Park (which deserves its own spotlight in this blog), and from here, it’s just a short walk to the Lake Michigan promenade — perfect for a breezy stroll, as long as Chicago’s famous winds don’t take you by surprise!

2. Strolling the Chicago Riverwalk

Chicago is famous for its historic architecture and stunning skyline dominated by towering skyscrapers. One of the best places to experience this unique blend of old and new is along the Chicago River and its Riverwalk. Winding through the heart of the city, the Chicago River offers beautiful views and a glimpse into the rich history of the metropolis. The walk takes about two km (1.25 miles) long, stretching from Lake Michigan to Lake Street which is around 30 to 45 minutes without stops. Especially during the summer months, this scenic walkway comes alive with numerous bars, restaurants, and cafés, making it the perfect spot to enjoy a leisurely stroll, grab a bite to eat, or simply soak in the urban atmosphere. The Chicago Riverwalk is a must-visit destination for anyone exploring the Windy City.

3. Wandering through Grant Park

Just south of Millennium Park lies the much larger Grant Park, often called “Chicago’s Front Yard.” This wide green space is home to museums, gardens, and wide-open lawns, making it a nice spot for both locals and visitors. One of its most famous landmarks is the Buckingham Fountain, one of the largest fountains in the world. Little fun fact: Built in 1927, this fountain was inspired by the grandeur of the Palace of Versailles and features a stunning water display, with jets shooting up to 150 feet in the air. From spring to fall, the fountain comes alive with hourly water shows, and after dusk, it’s illuminated with a dazzling light and music display, almost like a little piece of Las Vegas in the heart of Chicago. Grant Park is also home to major events like Lollapalooza and offers plenty of space to unwind, whether you’re taking a stroll, having a picnic, or simply enjoying the view of Lake Michigan. During my visit, I loved wandering through the park — there’s always something new to discover!

4. Enjoying the views at Navy Pier

What you also shouldn’t miss when visiting Chicago is Navy Pier! Thanks to its prime location on the shores of Lake Michigan, the city isn’t just blessed with city beaches and a picturesque waterfront — it has many other attractions to offer.

Navy Pier is like a mini amusement park, featuring an exciting mix of restaurants, bars, food trucks, and even some rides. It’s the perfect place to take a leisurely stroll, soak in the fresh lake breeze, and marvel at the stunning Chicago skyline. One of the best ways to enjoy the view? Hop on the iconic Centennial Wheel which offers panoramic sights of both the pier and the city beyond. Book your tickets in advance to skip the lines and secure your ride!

For a different perspective, consider embarking on a boat tour from Navy Pier. Whether you opt for a serene lake cruise or an adrenaline-pumping speedboat ride, you’ll see the city from a whole new angle.

Another fun way to explore the pier? Rent a multi-person bike with friends and cycle along the waterfront! My friends and I gave it a try, and it was an absolute blast. Just be prepared — Chicago’s famous winds can make it feel extra chilly, especially when you’re on the move. So, bring an extra layer to stay cozy! No matter how you choose to experience Navy Pier, one thing’s for sure — it’s definitely worth it!

5. Architecture Boat Cruise or Kajak

A boat tour along the Chicago River is an absolute must for anyone visiting the city. The best option is an Architecture River Cruise, where you won’t just drift along the water but also learn fascinating details behind the stunning buildings that line the water.

For those seeking a bit more action, you can also opt for a kayaking tour on the Chicago River. This unique experience allows you to paddle through the city while taking in the stunning skyline from a whole new perspective. When I visited, I was eager to try it, but the windy weather kept us from going out on the water. Next time, though, I’ll be sure to give it a go!

6. Tasting Chicago’s Famous Deep Dish Pizza

7. Visiting the Lincoln Park Zoo

I’ll be honest — I’m usually not the biggest fan of zoos. I much prefer seeing animals in their natural habitat, roaming free as nature intended. But Lincoln Park Zoo was a pleasant surprise! Nestled right in the heart of Chicago, this historic zoo offers a unique opportunity to observe wildlife up close.

We spent about two hours exploring the zoo, making the most of our visit. One of the highlights? The interactive experiences! You can watch feeding sessions, catch exciting animal training demonstrations, or simply marvel at the diverse species. From majestic big cats and playful primates to colorful tropical birds and fascinating reptiles, the zoo houses over 1,100 animals from all around the world — including many rare and endangered species.

Visitor information: One of the best things about Lincoln Park Zoo? It’s completely free! Unlike many major zoos that charge hefty admission fees, this one remains open to the public at no cost. When we visited, we didn’t even need to book a time slot — just walked right in and started exploring. Click here for more details!

8. Shopping along the Magnificent Mile

9. Exploring the Starbucks Roastery

If you’re a Starbucks lover — or simply a coffee enthusiast — you shouldn’t miss the Starbucks Reserve Roastery in Chicago! Located along the bustling Magnificent Mile, this four-story coffee paradise is like no other Starbucks you’ve ever seen. Imagine the irresistible smell of fresh coffee filling the air, a live roastery, a shop filled with exclusive coffee merch, and a bar on every floor.

Now, I’ll admit, I’m neither a Starbucks nor a coffee fan myself, but there was no way I was going to miss out on the irresistible aroma of freshly brewed coffee that fills the air (low-key obsessed with the smell). The main reason I went was actually because my friends, who are big coffee fans, insisted on it. And even as a non-coffee drinker, I found the experience to be quite cool!

Tip: Since the line at the Reserve Roastery can get pretty long during the day, the best times to visit are early in the morning or 1-2 hours before closing time.

10. Visit the Chicago Theatre

Summary of activities

• Millenium Park & The Bean (Cloud Gate)
• Chicago Riverwalk (Chicago River)
• Grant Park
• Navy Pier
• Architecture Boat Cruise or kajak
• Eat a Deep Dish Pizza
• Lincoln Park Zoo
• Magnificent Mile (For shopping)
• Starbucks Roastery
• Chicago Theatre

Summary of where to eat

• Giordano’s – famous deep dish pizza restaurant ^{(unpaid ad)}
• The Cheesecake Factory – offers a wide range of lunch and dinner options and of course desserts like Cheesecake ^{(unpaid ad)}

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