Latest Insights & Travel Guides

Six blocks of Roscoe Street disappear under classic cars, vendor tents, and decades of throwback music every September, and 2026

Asked my dispatcher to explain this one. He gave up halfway through. Landed on “it’s a festival where you eat

I’ll be honest — I used to think black car service was just a fancier name for a regular ride.

Old Town’s had the row houses forever. The comedy club too. Decades of neighborhood character crammed into a few blocks

Chicago’s never had this tournament before. Not once, in the whole history of it. That changes come September, when Medinah

Thirty-three years, typically around the same weekend, Independence Day. Turns out that pattern broke this year for the African Caribbean

Grand Cru. Tacos & Tequila. The Hamburger Hop. Those are three of the signature events inside Chicago Gourmet, and if

Had a driver ask me last week if we’d written anything up on this one yet. A rider kept asking

My dispatcher brought this one up last week. Said it’s the festival where you genuinely never know what you’re getting,