About Jill Halpin – Chicago & Midwest Travel Expert

I’m Jill Halpin, the founder of LittleChicagoGuide.com. I’ve lived in Chicago part-time for about ten years, and my husband’s family is from here, so this city has been part of my life well beyond the visits. This site is where I share what I’d tell a friend who’s coming to town.

I’m also a former newspaper and magazine journalist with a master’s degree in information science, which is a fancy way of saying I care a lot about getting the details right: the date, the CTA stop, the price at the door.

How Chicago Became My Second Home

Chicago came into my life through family. My husband’s family is from here, and over the last decade I’ve split my time between Chicago, Northern Michigan, and Southeast Michigan. That means I’m not a tourist here and I’m not a lifelong local either, which turns out to be a useful place to write from: I still notice what confuses visitors, and I know enough to tell them what to do about it.

I founded Halpin Media Group in 2019, starting with MyMichiganBeach.com, and launched LittleChicagoGuide.com in July 2023. Its sister site, LittleMichiganGuide.com, covers Michigan’s towns, food, and culture.

From Newsrooms to Information Science

I started out as a journalist, writing for newspapers and magazines and later working at Gannett in the 2000s. Then I went back to school for a master’s in library and information science, where the whole job is organizing information so people can actually find and trust it.

Those two careers shaped how I build every guide here. The reporter in me wants the primary source. The information scientist in me wants it organized so you can plan a trip in five minutes instead of fifty.

Where You’ve Seen Me

I’ve appeared on FOX 32 Chicago‘s Good Day Chicago and on WGN Chicago to talk Chicago travel. I’m a contributor to FOX 17 West Michigan, where I’ve also covered Chicago trips, and to WDIV Local 4 in Detroit. I’ve also appeared on FOX 2 Detroit, been featured on NewsNation, and been written up in The Washington Post, The Detroit News, and the Detroit Free Press.

You can watch segments and see the full list on my media appearances page.

How Every Guide Is Made

Here’s what you can count on every time you read a guide on this site:

• Checked against the source. Dates, hours, and prices come from the venue’s or organizer’s own website, not from review apps or aggregator listings.
• Honest about what I’ve seen. When I’ve been somewhere, I tell you what I noticed. When I haven’t, I say what the official source says and don’t pretend otherwise.
• The details other guides skip. Which L stop, what parking really costs, dog policies, accessibility, and when an event ends earlier than you’d expect.
• Kept current. Seasonal guides are updated each year, and places that close come off the list.
• Not for sale. If a business is a paid partner, the page says so, and payment never changes where or how a place is ranked. See my advertising and affiliate disclosure.

Every guide is reviewed and approved by me before it’s published. If you spot something that’s changed, I genuinely want to know, because Chicago changes fast.

A Personal Note

Some of my favorite Chicago days are the simple ones. When my kids were younger, Lincoln Park Zoo was a must, because you can see the animals up close, and lunch at R.J. Grunts across the street was their favorite. I also think Navy Pier and the Chicago Children’s Museum are a must with kids.

I love the Lincoln Square Apple Fest, which works as both a family outing and a date night. And when kids need to burn off energy, the lakefront parks, from Millennium Park to Lincoln Park, are always my suggestion.

Media and Partnerships

Producers and editors can reach me at info@littlechicagoguide.com for Chicago and Midwest travel segments, seasonal story ideas, and expert comment. Tourism boards and businesses can learn about partnerships on my Work With Us page.

New to the site? Start with my first-time visitor’s guide to Chicago, then pick a neighborhood and go from there.