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Pride Journey: Chicago


Chicago, often dubbed the "Windy City," stands tall as a vibrant metropolis known for its rich history, stunning architecture, and diverse cultural scene. But beyond its iconic skyline and deep-dish pizza, Chicago also serves as a prominent hub for LGBTQ culture, offering a dynamic and inclusive environment for individuals of all sexual orientations and gender identities.


The city is a quick three-hour drive from my hometown of Indianapolis, so it has become one of my favorite go-to destinations. It is also home to arguably the premier LGBTQ festival of the summer, Market Days. This was my second time attending the event and I was really excited to see headliners Betty Who and Crystal Waters. The street festival takes place every year in early August in the Northalsted neighborhood – formerly known as Boystown. Market Days is a unique festival in that it offers something for everyone.


The festival traces its origins back to 1980 when it began as a small, grassroots event organized by the Northalsted Business Alliance, a group of LGBTQ business owners and community members. Over the years, the festival has grown exponentially, evolving into one of the largest and most anticipated LGBTQ events in the Midwest. What started as a humble street fair has become a colorful extravaganza that attracts thousands of attendees each year.


For this visit, I stayed at Freehand Hotel, a budget-friendly property located in the heart of Chicago’s River North neighborhood, providing easy access to shops, restaurants, and attractions. The property is perfect for groups of friends and even offers rooms with bunkbeds if you are looking to share a room with your crew. Broken Shaker bar located just off the lobby is really the highlight of the hotel. The tiki-inspired space is cozy and transports guests to an island vibe that makes you forget you are in the heart of a major city. For those looking for a bit of luxury, check out Freehand’s two-story penthouse suite.



LGBTQ culture in Chicago has deep historical roots that trace back to the early 20th century. In the 1920s and 1930s, LGBTQ individuals found refuge in establishments such as speakeasies and private parties during Prohibition. Despite the challenges posed by discriminatory laws, Chicago's LGBTQ community began to emerge and form its own social networks.


By the 1960s, LGBTQ activism gained momentum in the city. Organizations like the Chicago Gay Liberation and Gay Activists Alliance started advocating for equal rights and visibility. The 1970s witnessed the founding of iconic LGBTQ spaces, such as Little Jim's, a bar that became a haven for the community, and the Gerber/Hart Library, a repository of LGBTQ literature and history.


Present-day Chicago boasts a plethora of LGBTQ-focused spaces that celebrate diversity and inclusion. The Northalsted and Andersonville neighborhoods are home to a multitude of LGBTQ-owned businesses, bars, clubs, and restaurants, creating a welcoming environment for locals and visitors alike.


Chicago's LGBTQ culture is a testament to the city's commitment to diversity, acceptance, and progress. From its historical roots to its vibrant community spaces and annual celebrations, the Windy City stands as a beacon of LGBTQ pride and unity. As the LGBTQ rights movement continues to evolve, Chicago remains a city that not only acknowledges its LGBTQ community but actively celebrates their contributions, experiences, and voices.


The Windy City boasts a plethora of architectural landmarks that captivate both residents and visitors. The Willis Tower (formerly known as the Sears Tower), completed in 1973, reigned as the world's tallest building for decades and remains an iconic symbol of Chicago. Its innovative use of bundled tube construction and its Skydeck, offering breathtaking views of the city, attracts millions of tourists each year. If you are adventurous, visit The Ledge located on the top floor of the tower, and peer down through the glass floor to the city below. This experience is not for the faint of heart.



Chicago's architectural legacy is forever intertwined with the invention of the skyscraper. In the late 19th century, architects like Louis Sullivan and Daniel Burnham challenged traditional building methods, ushering in a new era of vertical construction. The Home Insurance Building, constructed in 1885, is often credited as the world's first skyscraper, standing ten stories tall and featuring an innovative steel frame structure. This marked the beginning of Chicago's dominance in skyscraper construction, where architects continuously pushed the boundaries of height and design.


It would benefit you to purchase a CityPass prior to your visit. The pass helps you book popular experiences and attraction tickets. Before heading to Market Days, I took a wonderful architectural river cruise which really gives guests a perspective of how diverse the city is when it comes to design. As we snaked along the Chicago River, our wonderful guide pointed out the architectural wonders that dot the city’s skyline.



If you are looking for a fun autumn adventure, I highly recommend checking out Chicago for some of the best food, architecture, culture, and nightlife in the country.


Enjoy the Journey!

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