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!