Little Italy Is Perfectly Positioned as Chicago Celebrates Route 66's 100th Birthday This Summer
By Socialhood News · Il/Chicago/University Village Little Italy ·
University Village Little Italy is sitting at the intersection of history and excitement this Memorial Day week, as Chicago kicks off a yearlong celebration of one of America's most iconic roads. Chicago is honoring the 100th anniversary of Route 66 throughout 2026, celebrating the city's place as the official starting point of the legendary highway — and Taylor Street's storied Near West Side corridor sits squarely in the spirit of that blue-collar, immigrant-built American story.
The Route 66 Centennial isn't the only citywide magnet drawing visitors to Chicago's Near West Side this summer. The Obama Presidential Center — opening this summer 2026 on a 19-acre campus in nearby Jackson Park — is expected to be one of the city's most significant new cultural destinations, featuring a museum, auditorium, a Chicago Public Library branch, and community programming spaces. As tourism energy builds across the South and Near West sides, neighborhoods like Little Italy stand to welcome a wave of new foot traffic to Taylor Street's beloved restaurants, bakeries, and cafés.
For a neighborhood already stacked with Italian beef festivals, Taylor Street celebrations, and decades of culinary legacy, the summer of 2026 is shaping up to be one of the most dynamic in recent memory. Heading out to explore this weekend? Tag @SocialhoodChicago with #LittleItalyChicago and show us your favorite Taylor Street moment!
Sources:
1. https://www.choosechicago.com/meeting-planners/plan-your-chicago-meeting/chicago-meeting-ideas/whats-new-in-chicago/
2. https://www.choosechicago.com/neighborhoods/little-italy-university-village/