As someone who has lived in multiple cities and countries throughout my life, every place has become a part of me but let’s just say (and I’m sure my friends would agree), I don’t boast about the other places I’ve lived in as much as I do about Chicago. Hence, it only feels appropriate to kick off 2024’s first travel adventure post with an homage to my beloved Windy City.

In this post, I aim to provide a general overview of the city, share some of my favorite (rooftop) bars and restaurants, give some recommendations regarding activities and sights as well as present some of my favorite (hidden) gems.

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My Chicago Story

I will always remember my first time in Chicago. I was studying in Washington D.C. at the time. In between semesters, right at the end of Christmas break, I wanted to take a solo trip to an American city. Since I had been to Florida during Thanksgiving break and was saving the West Coast for a bigger trip, I decided on the Midwest. So in January 2015, the day after New Year’s Day I boarded a Spirit flight (I will never voluntarily take that airline again), and took off to Chicago for the very first time.

My first day in Chicago, September 4, 1983. I set foot in this city, and just walking down the street, it was like roots, like the motherland. I knew I belonged here.

Oprah Winfrey

With little expectations and nobody I knew in the city, I booked myself into the Palmer House, a timeless, elegant and historic Chicago hotel. Prices were relatively affordably due to the off-season travel dates. Apparently, January is the worst time of the year to visit the city. I already assumed it was going to be cold. However, I did not expect nor was I prepared for the temperature shock: it was -25°C (-13°F) on the day of my arrival.

Despite the bitterly cold temperatures and the freezing wind, I fell in love with Chicago instantly. The astounding architecture, the vast preserved green and open spaces including the lake, the vibrant music scene, amazing food, iconic neighborhoods and lastly the friendly and down-to-earth Midwesterners – the city has got it all and it has never failed to captivate me ever since. Similar to what Oprah described, I also knew immediately: I belonged there.

Thus, in 2017, I moved to Chicago for a one year traineeship at the German American Chamber of Commerce of the Midwest. Not only was it one of the best decisions of my life because of the work experience I gained but also because my time in Chicago was one of the best years of my life.

Writing about my memories, experiences and lessons learned and the love I have for this city and putting it in one single post is impossible. However, I do want to share a bit of history about the city of Chicago, its neighborhoods, its culinary scenes, several well-and-lesser known tourist attractions as well as some fun things to do if you ever find yourself in Chi-town.

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About Chicago & Its History

As the third-most populous city in the US (after NYC and LA), Chicago is located in the state of Illinois, in the Midwest on the southwestern shore of Lake Michigan. While often referred to as the “Windy City”, the origin of this nickname is debated, with theories ranging from the city’s weather to political hot air.

• Chicago began as a small trading post (Fort Dearborn) and was officially incorporated in 1833.
• In 1871 a devastating fire, known as the Great Chicago Fire led to widespread destruction but also spurred modernization and rebuilding efforts.
• The city’s strategic location and transportation infrastructure fueled rapid industrialization, making it a key hub.
• Chicago rose to fame when it hosted one of the first world fairs: the World’s Columbian Exposition in 1893, showcasing progress and innovation.
• Since then it thrived in the early 20th century, becoming a major center for industry, commerce, and culture and hosting another world fair: Century of Progress Exposition of 1933–34.
• After WWII, Chicago continued to grow and diversify its economy, playing a vital role in civil rights activism.
• Today, Chicago is a global city with a diverse economy, cultural institutions, and architectural significance yet it faces challenges, including issues of inequality and violence, but it remains a vibrant and dynamic metropolis.

Eventually, I think Chicago will be the most beautiful great city left in the world.

Frank Lloyd Wright

Throughout its history, Chicago has evolved from a small town to a major global city, facing multiple challenges but demonstrating resilience and adaptability. As such, a symbol chronicling the complex and rich history of the city is the Chicago flag. I own a poster, a sign and a necklace of the Chicago flag which are obvious signs of my obsession with this city.

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Chicago’s Neighborhoods

Home to a rich tapestry of more than 77 unique community areas, Chicago is known for its diverse neighborhoods. Each with its own distinct vibes, restaurants, boutiques, museums, and friendly locals, it’s the variety of character in each of these neighborhood’s that make Chicago so liveable. Everybody is welcome and it’s easy to feel a sense of belonging.

I used to live in Lakeview and absolutely adored it. But here’s a brief summary of some notable neighborhoods and what you can expect in each of them:

List + more info on Chicago’s neighborhoods (click the drop down)

Lakeview (where I used to live):

Home to Wrigley Field and Boystown, known for its lively atmosphere, diverse communities, and lakefront access. Personally, I loved living in this neighborhood and never would have wanted to move. While there are some really cool other neighborhoods as well, I’ll remain bias haha.

The Loop:

Chicago’s central business district, known for iconic skyscrapers, theaters, and Millennium Park.

River North (where my office used to be):

Trendy and artsy neighborhood with galleries, nightlife, and upscale dining.

Lincoln Park:

A residential area with a large park, a zoo, and a mix of historic and modern architecture.

Wicker Park and Bucktown:

Hip and eclectic neighborhoods with a vibrant arts scene, boutiques, and diverse dining options.

Hyde Park:

Located around the University of Chicago, it has a scholarly atmosphere, historic architecture, and cultural institutions.

Pilsen:

A predominantly Latino neighborhood known for its colorful street art, Mexican culture, and vibrant community.

Chinatown:

A cultural hub with authentic Chinese cuisine, festivals, and a distinct atmosphere.

Logan Square:

Trendy and diverse, featuring historic architecture, boutique shops, and a thriving food scene.

Uptown:

A culturally rich and more residential area with historic theaters, diverse communities, and an evolving arts scene.

South Side:

The South Side is a large, diverse area with historic districts, student hangouts, and residential blocks lined with row houses. It holds a key place in African-American history, with writers, musicians, and politicians, including Barack Obama, among its former residents.

These neighborhoods collectively contribute to Chicago’s mosaic of cultures, lifestyles, and experiences, making the city a dynamic and diverse urban landscape.

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Cuisine & Dining

Chicago is a vibrant culinary hub known for its diverse and iconic food scene. Living there, I had never explored so many different restaurants and bars. I almost never cooked because there were too many places I wanted to try out and too little time.

As with all of my travel adventure posts, I try to limit my favorite restaurants, bars & cafés to a list of 5. However, if you’re looking for more inspiration, feel free to subscribe to my blog and you will receive my Google Maps List as well.

Top 5 Favorite – Chicago Edition

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More Food Options

Local Specialties

Chicago is renowned for its unique and delicious local specialties:

• The city is synonymous with deep-dish pizza, a thick-crusted pizza loaded with cheese, sauce, and various toppings. I recommend Lou Malnati’s Pizzeria to get an authentic taste of the Chicago specialty.
• Another must-try is the Chicago-style hot dog, featuring an all-beef frankfurter topped with mustard, onions, relish, tomatoes, pickles, sport peppers, and celery salt or the Italian beef sandwiches, thinly sliced beef in au jus. Both delicacies can be tried at Portillo’s, an iconic staple in Chicago’s restaurant scene.
• Garrett Popcorn, a mix of caramel and cheese-flavored popcorn, is also a local favorite.

Food Festivals

Chicago hosts several food festivals that celebrate its diverse culinary offerings:

• The Taste of Chicago is a renowned event featuring a wide array of food from local restaurants, live music, and cultural activities.
• Chicago Gourmet is another must-attend festival, bringing together top chefs and food enthusiasts to showcase the city’s culinary excellence.
• The Christkindlmarket Chicago is the most authentic traditional holiday market of its kind outside of Europe, held annually at Daley Plaza it offers a unique shopping experience, family-friendly events & intercultural activities as well as foods.
• Lastly, there are multiple street festivals throughout Chicago’s neighborhoods all year round. Just check this event calendar for a list.

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Cultural Scene

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Architecture and Landmarks

This wouldn’t be a wholesome blog post about Chicago, if it did not address the architecture as the city is renowned for its rich architectural heritage, spanning a diverse range of styles that showcase the city’s evolution over time

From iconic historic structures such as the Water Tower, a survivor of the Great Chicago Fire, to contemporary landmarks like the Cloud Gate, fondly known as “The Bean,” located in Millennium Park, the city offers a captivating blend of the old and the new.

For those interested in Chicago’s architecture, I highly recommend the boat tours on the Chicago River providing views of historic and modern buildings. Additionally, walking tours in areas like the Gold Coast offer a closer look at architectural highlights and the city’s cultural history. Whether admiring the grandeur of historic landmarks or marveling at the sleek lines of modern masterpieces, Chicago’s architecture invites visitors and locals alike to embark on a journey through time and design, uncovering the stories etched into the city’s skyline.

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Sports

Chicago is a sports-rich city with a passionate fan base, hosting several major professional sports teams across different leagues. Here’s a quick summary of the prominent sports teams in Chicago:

Whether you are an American sports fan or not, if you find yourself in Chicago, make sure to take a look at the sports schedule. Whether it’s catching a game of the Cubs in Wrigley Field or checking out the Bulls at the United Center – you will be entertained and won’t regret it.

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Chicago Bucketlist

I miss everything about Chicago, except January and February.

Gary Cole

While I would try to avoid a trip in January or February, Chicago is ALWAYS worth a visit! There are a few activities, sights and to-do’s that should be part of any itinerary. Below I compiled a list of some of my favorite things to do in the city.

These are just a few suggestions, and there’s much more to explore in the Windy City! Is there anything I missed? Let me know what else you would add in the comment section!

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She is always a novelty; for she is never the Chicago you saw when you passed through the last time.

Mark Twain

I fell in love with Chicago the first time I set my eyes on the city almost 10 years ago. It was a brutally cold January day when I found myself home away from home. This beautiful, massive, urban city welcomed me with open arms ever since, wrapped me tight into its warm (and sometimes bitterly cold) embrace. Always a novelty whenever I visit but Chicago always feels like home.

I truly hope you enjoyed my take on Chicago and what a trip to this remarkable city should entail. I would love to hear if you have ever been and whether what I wrote resonates with you. Please let me know in the comments and also tell me what I might have missed. I appreciate any kind of feedback! If you’ve never been, I wish you a chance to get to visit my favorite city and make up your own mind but I hope I could inspire you to maybe add Chicago to your itinerary in the future. Thanks for reading along!

Sincerely, The Blonde Yeti