Sharing Chicago With You
Whether you call it The Windy City, The Second City, or The City of Big Shoulders, one thing is undeniable—Chicago is one of the greatest cities in the world. From world-class museums and shopping to a stunning lakefront, iconic architecture, and vibrant neighborhoods, Chicago offers something for everyone.
From hidden gems to iconic landmarks, food festivals to cultural hotspots, this site is your go-to source for discovering what makes Chicago truly unforgettable.
That’s why I created Little Chicago Guide—a carefully curated resource designed to help you explore and fall in love with this incredible city, just as I did.
Work With Us
At LittleChicagoGuide.com, we love partnering with brands, destinations, and organizations that share our passion for exploring Chicago and the Midwest.
Whether you represent a travel brand, local business, hotel, tourism board, or event, we offer creative ways to collaborate — from sponsored stories and brand features to social media promotions, giveaways, and TV coverage tie-ins.
Founder Jill Halpin is a recognized Chicago and Midwest travel expert who regularly appears on Fox 32 Chicago, Fox 17 West Michigan, and other media outlets, reaching a combined audience of thousands across TV, web, and social media.
Let’s work together to inspire locals and visitors to discover your brand or destination.
👉 Interested in collaborating? Contact us here to start the conversation!
As Seen On: Media & Recognition
Jill Halpin and Little Chicago Guide have been featured on television and in the press for their trusted travel insights.
Jill has appeared on Fox 32 Chicago’s Good Day Chicago and Fox 17 West Michigan, sharing Chicago and Midwest travel tips with viewers across the region. Her work has also been featured in publications including The Detroit News, Wanderlog, and the Loyola Phoenix.