Making the ordinary extraordinary in Chicago since 2006.
Since 2006, Windy City has been known across Chicagoland for putting safety first and turning ordinary trips into extraordinary experiences. With one of the most diverse fleets in the industry from sedans and limousines to motorcoaches, and a team of exceptional chauffeurs, Windy City has earned its place as one of the region’s leading transportation providers.
That reputation is backed by national recognition: Motorcoach Operator of the Year (2016), National Operator of the Year (2019), and eight years as “Best Transportation” from Illinois Meeting and Events Magazine. Windy City joined TBL Group in 2024 and now operates as Windy City Transportation.