Founder of LittleChicagoGuide.com
Travel Journalist • TV Contributor • Chicago Enthusiast
I’m Jill Halpin — the founder and editor of LittleChicagoGuide.com, a Chicago-based travel and lifestyle site created to help you discover the best of the city and its surrounding Midwest gems.
As a long-time journalist and travel expert, I’ve built a career around exploring destinations that inspire. My mission is simple: to make it easy (and fun!) for you to experience Chicago like a local — from iconic neighborhoods and must-try restaurants to hidden parks, seasonal festivals, and weekend road trips just beyond city limits.
My Story
My connection to Chicago runs deep. With family roots here and years spent visiting before finally relocating, I fell in love with the city’s energy, creativity, and constant evolution.
Splitting my time between Chicago and Michigan, I’ve spent years uncovering the Midwest’s most memorable places — big and small. That combination gives me a unique perspective: I understand what visitors want to see and what locals love most about their hometown.
Professional Background
- Public Speaker & TV Guest: Regularly invited to discuss local tourism trends, family getaways, and seasonal travel ideas across multiple Midwest media outlets
- Journalism & Media: Bachelor’s in Journalism and Master’s in Library & Information Science from Wayne State University (Detroit, MI)
- TV Contributor: Appearances on Fox 32 Chicago’s Good Day Chicago and Fox 17 West Michigan, sharing insider Chicago and Midwest travel tips
- Print & Digital Media: Featured in outlets such as The Detroit News, Wanderlog, and The Loyola Phoenix
- Founder & Editor: LittleChicagoGuide.com and MyMichiganBeach.com — trusted online resources for regional travel inspiration
In the Media
I’m proud to represent Chicago travel on-air and in print. My recent features include:
- Fox 32 Chicago: Good Day Chicago – Best Fall Road Trips from Chicago
- Fox 17 West Michigan: Morning News – Tips for First-Time Visitors to Chicago
- The Detroit News: Highlighting the best of Midwest travel
- Wanderlog and The Loyola Phoenix: Showcasing Little Chicago Guide as a trusted local resource
About My Expertise
With a background in journalism and years of hands-on travel experience, I focus on creating authentic, well-researched guides that readers trust. Each article on Little Chicago Guide is based on personal visits, real recommendations, and conversations with locals. My work combines storytelling with practical tips — because I believe great travel content should both inspire and help you plan your next adventure.
A Personal Note
When I’m not writing or appearing on TV, you’ll usually find me exploring Chicago’s neighborhoods, or walking along the lakefront. I believe the best travel advice comes from experience — and I love sharing the discoveries that make this region so special.
Work With Me
I love collaborating with tourism boards, hospitality partners, and Midwest-based brands that share my passion for authentic travel storytelling. If you’d like to discuss a campaign, feature, or partnership, reach out directly at: info@littlechicagoguide.com
You can also visit our Work With Us page for collaboration details.
Connect
Follow me on Instagram, Facebook, and Pinterest for daily travel ideas and behind-the-scenes adventures.