Travel Site Reveals Illinois Has One of the Coolest Streets on Earth
When a global travel giant like Time Out drops its annual list of the World’s Coolest Streets, you expect places like Rio, Tokyo, Melbourne, and Paris to dominate. And they do. But what you might not expect is that one of those globally celebrated streets is hiding right here in Illinois. Not Chicago’s Magnificent Mile… not Clark Street buzzing outside Wrigley Field… something much smaller, friendlier, and way more “neighborhood cool.”
The U.S. Streets That Made the Global List
Only a handful of American spots cracked the top 30 this year. New York’s Orchard Street, Portland’s Mississippi Avenue, and Austin’s East 6th Street all landed on the list, major destinations with big personalities. And yet, Illinois still found a way to stand out among them. That’s impressive company.
So, Where Is Illinois’ Coolest Street?
MORE: Illinois Pizzerias With The Highest Scores From Dave Portnoy's One Bite Reviews
Time Out calls it “the village within the city,” and it sits just a mile west of Wrigley Field. If you're heading to a Cubs game, you might have unknowingly walked right past it. This charming stretch is full of indie shops, family-owned restaurants, local bars, strollers, bikes, and one of the friendliest summer festivals in the Midwest.
Say hello to Roscoe Street in Chicago’s Roscoe Village, officially ranked the 28th Coolest Street in the World.
What Makes Roscoe Street So Special?
From Volo Wine Bar and Four Moon Tavern to vintage finds, bike rentals, and the always-fun Retro on Roscoe festival, it’s pure neighborhood magic. It feels like a tiny town tucked into a huge city, the perfect pre- or post-Wrigley detour.
Explore Even More Cool Streets
If you want to see all 30 destinations, from Rio to Rome, check out the full list at TimeOut.com.
And if you make the trip? Send me your Roscoe Street photos!
READ MORE: 19 Best Things To Do on Your First Trip to Chicago
LOOK: Best scenic drives in Illinois
Gallery Credit: Stacker