Welcome to Logan Square: Where Vintage Charm, Creative Energy, and Urban Cool Collide in One of Chicago’s Most Iconic Neighborhoods

Tucked between the North and Northwest Sides of Chicago, Logan Square is a dynamic, walkable neighborhood that perfectly blends historic elegance, artistic spirit, and city convenience. Centered around its namesake Logan Square Boulevards — a stunning 19th-century traffic circle designed by Frederick Law Olmsted — this vibrant community stretches from Fullerton Avenue to the south, to Armitage Avenue to the north, and from Western Avenue to the east, to Kedzie Avenue to the west.

More than just a trendy hotspot, Logan Square is a cultural epicenter where vintage bungalows meet craft cocktail bars, where bike lanes buzz with commuters, and where every block tells a story of evolution, creativity, and community.

🌳 A Legacy of Beauty and Innovation

Logan Square was born in the 1890s as a Gilded Age escape for Chicago’s elite, with grand homes, tree-lined boulevards, and a centerpiece inspired by the Champs-Élysées. The Logan Square Monument and surrounding park were once the heart of a wealthy suburb — but as the city grew, so did its diversity and dynamism.

Today, the neighborhood honors its past while embracing the future. The historic boulevards are protected as part of the Chicago Landmark District, while the surrounding streets pulse with new energy, new faces, and new ideas.

🍻 The Epicenter of Chicago’s Creative Scene

Logan Square is synonymous with cool — but it’s a cool that feels earned, not forced. The main corridors — Milwaukee, Logan, and Kedzie Avenues — are lined with:

  • Craft breweries like Revolution Brewing (Chicago’s first brewpub), Half Acre, and Spiteful Brewing

  • Trendsetting restaurants: Dove’s Luncheonette, The Violet Hour (a pioneer in craft cocktails), Superdawg Drive-In (a retro icon)

  • Indie coffee shops, record stores, and vintage boutiques

  • Murals, pop-up art shows, and street festivals that celebrate local talent

It’s a place where you can bike to brunch, catch live music at an underground venue, and end the night at a speakeasy hidden behind a bookshelf.

And yes — it’s still incredibly walkable and bike-friendly, with the 606 Trail just blocks away and the North Branch Trail running nearby.

🏡 Housing: From Greystones to Modern Lofts

Logan Square offers one of the most diverse and desirable housing markets in Chicago:

  • Restored greystone mansions and early 20th-century two-flats

  • Vintage courtyard buildings with ivy-covered courtyards

  • Modern condos and adaptive reuse lofts in former factories

  • Bungalows and single-family homes with renovation potential

While prices have risen due to demand, it remains more affordable than Lincoln Park or Bucktown, making it a top choice for young professionals, creatives, families, and investors who want character, location, and value.

🚇 Connected, Central, and Always Moving

Logan Square is one of the most transit-rich neighborhoods in the city:

  • Served by the CTA Blue Line at Logan Square and Kedzie stations — just 15 minutes to the Loop

  • Multiple bus routes: #50 Damen, #56 Milwaukee, #70 Division

  • The 606 Trail starts nearby, connecting to Wicker Park and Humboldt Park

You’re just:
📍 10 minutes from Wicker Park
📍 20 minutes from O’Hare Airport
📍 5 minutes from the Kennedy Expressway

Whether you're commuting, biking, or bar-hopping, everything is within reach.

🌿 Parks, Trails & Outdoor Living

Beyond the nightlife, Logan Square is deeply rooted in green space and recreation:

  • Logan Square Park – host to farmers markets, outdoor movies, and summer concerts

  • The 606 (Bloomingdale Trail) – an elevated park perfect for walking, running, or biking

  • Ridgeway Avenue Park and Humboldt Park within easy reach

  • The North Branch Trail for scenic rides along the river

Residents enjoy a rare balance: urban energy with outdoor escape.

❤️ A Community That Values Inclusion & Identity

Logan Square is proudly diverse and evolving — with deep roots in Puerto Rican, Mexican, Eastern European, and LGBTQ+ communities. While rising popularity has sparked concerns about gentrification, strong tenant unions, community land trusts, and organizations like Logan Square Neighborhood Association (LSNA) are working to:
✅ Preserve affordable housing
✅ Support small businesses
✅ Promote equitable development
✅ Strengthen schools and youth programs

This is a neighborhood that fights for its soul — and believes growth should include everyone.

 

Neigborhood Experts