The Chicagoland Guide explores how the Chicagoland area actually works, through conversations about housing, infrastructure, development, and the civic decisions shaping the region’s future.
Hosted by Aaron Masliansky, a Chicago-area real estate advisor and urban planning graduate, the show features in-depth discussions with mayors, developers, policy leaders, business owners, and cultural institutions. Rather than surface-level neighborhood highlights, each episode examines the forces influencing growth, investment, and community life across Chicagoland.
For residents, investors, and civic leaders who care about long-term thinking and how place shapes opportunity, The Chicagoland Guide offers thoughtful, grounded conversations about the region’s trajectory.
Episode 146: Exploring Hyde Park Through the 57th Street Art Fair
In Episode 146 of The Chicagoland Guide, Aaron Masliansky sits down with Cate Slighton of the 57th Street Art Fair to explore the history, culture, and community that have made Hyde Park one of Chicago’s most distinctive neighborhoods. As the fair prepares for its 79th year, Cate shares the story of how a small gathering of local artists evolved into the oldest juried art fair in the Midwest. The conversation also dives into Hyde Park’s artist colonies, the legacy of the 1893 World’s Columbian Exposition, urban renewal, the influence of the University of Chicago, the Obama Presidential Center, and the role that art and public spaces play in creating vibrant communities. Whether you’re a longtime Chicagoan or discovering Hyde Park for the first time, this episode offers a fascinating look at one of the city’s most unique and enduring cultural destinations.In Episode 146 of The Chicagoland Guide, Aaron Masliansky sits down with Cate Sleighton of the 57th Street Art Fair to explore the history, culture, and community that have made Hyde Park one of Chicago’s most distinctive neighborhoods. As the fair prepares for its 79th year, Cate shares the story of how a small gathering of local artists evolved into the oldest juried art fair in the Midwest. The conversation also dives into Hyde Park’s artist colonies, the legacy of the 1893 World’s Columbian Exposition, urban renewal, the influence of the University of Chicago, the Obama Presidential Center, and the role that art and public spaces play in creating vibrant communities. Whether you’re a longtime Chicagoan or discovering Hyde Park for the first time, this episode offers a fascinating look at one of the city’s most unique and enduring cultural destinations.
13 May 2026
Episode 145: Mayor Nancy Rotering on Highland Park’s Future, Housing, Community, and Leadership
In Episode 145 of The Chicagoland Guide, Aaron sits down at Highland Park City Hall with Mayor Nancy Rotering for a thoughtful conversation about what makes Highland Park such a distinctive place to live, work, and raise a family. From Ravinia, Taste of Highland Park, and the city’s unique neighborhoods to housing affordability, inclusionary zoning, senior living, and the redevelopment of the former Solo Cup site, Mayor Rotering shares how Highland Park is planning for growth while staying true to its character. They also discuss civic leadership, community resilience, accessibility, and what it takes to build a suburb that remains vibrant for generations to come.
29 Apr 2026
Episode 144: How Housing, Infrastructure, and Development Actually Work in Skokie with Johanna Nyden
In this episode, Aaron sits down with Johanna Nyden, Community Development Director for the Village of Skokie, for a grounded conversation about how housing, infrastructure, and development actually work at the local level. They unpack what’s really driving housing costs, the realities of aging housing stock, why permitting can feel frustrating, and how municipalities balance growth, safety, and affordability. Johanna also shares insight into “missing middle” housing, infrastructure constraints, and what it takes to keep communities livable as costs rise.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
YouTube views
8,609
Score snapshot 15 Sept 2025
Apple Podcasts (US)
4.9 / 5
18 ratings
Podcast Authority Score: 66 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
85
Social presence
0
YouTube
68
Engagement
51
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Guest appearances
Books guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
Questions about Inside the Skev
Who hosts Inside the Skev?
Aaron Masliansky host the show. Published by Aaron Masliansky.
How often do new episodes come out?
The show publishes weekly, based on its RSS feed.
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Yes. Guests have been identified in episode analyses.
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