Chicago, Illinois

As a born-and-raised Chicagoan (Go Cubs, and don’t even come at me about the White Sox) , I can't help but grin every time I catch that first glimpse of the skyline. There's something magical about returning to the Windy City for me - the way the sunlight glints off Lake Michigan, the unmistakable rumble of the L train, and yes, even that notorious gust that threatens to snatch your hat while making your nose run as you round a corner. Chicago, for me, is a feeling.

It's the thrill of your first bite into a proper deep-dish pizza, the camaraderie of cheering (or commiserating) with fellow Cubs fans, and the simple joy of a stroll through Millennium Park. Whether you're a fellow native coming home or a first-time visitor, Chicago has a way of welcoming you with open arms. So grab your comfiest walking shoes and an empty stomach - we've got a lot of ground (and food) to cover!

Exploring the Windy City…

  • The Silversmith Hotel

    Have you ever wondered what it would be like to sleep in a jewelry box? Well, maybe not exactly, but the Silversmith Hotel in Chicago's Loop might be the next best thing! Nestled at 10 South Wabash, this quirky little boutique hotel…

  • Photos Around the City

    We visit OFTEN! So sometimes, the best way to get a vibe for a location is to check out all the photos. Tour the Windy City via camera with me! Ready?

Chicago is the resilient underdog of all cities (I’m looking at you, Cubbies). Be part of the narrative.

Although I’ll never move back to Chicago, it’s still a place that feels like home.