Chicago River with downtown skyline, bridges, and architecture tour boat

Discover Chicago Like You Live Here

Skip the tourist traps. Get neighborhood secrets, local favorites,
and insider tips from someone who calls Chicago home.

✓ As Seen on Fox 32 Chicago | ✓ 200+ Local Guides | ✓ Updated Weekly

As Seen on: Fox 32 | Fox17 West Michigan | WDIV Detroit

Good Day Chicago | 12-4-25

Amazing ways to share Chicago with friends and family + holiday giveaway!

Jill Halpin, Chicago travel expert on Fox 32 Chicago's "Good Day Chicago"

“Good Day Chicago” | 10-2-25

Jill Halpin, Chicago travel expert, shares amazing Fall getaways from Chicago.

Chicago travel expert Jill Halpin on Fox17 West Michigan talking about Chicago travel

Fox17 West Michigan | 3-9-25

Make the most of St. Patrick’s Day in Chicago with Fox17 West Michigan.

Fox32 Chicago | 8-26-25

Last-minute Labor Day escapes from Chicago across the Midwest.

What Brings You to Chicago?

margie's candies, a must-visit in Chicago's Bucktown neighborhood

Explore Neighborhoods

Explore Chicago’s best neighborhoods with our local guides. Find where to stay, hidden gems to discover, and authentic restaurants in every corner of the city.

Browse Neighborhoods
vibrant Chicago skyline, a top city view

First Time Visiting

Plan your perfect Chicago trip with our complete guide—where to stay by neighborhood, 3-5 day itineraries, how to get around, best time to visit, and insider tips from locals.

Start Here
view of lake Michigan in Chicago from Chicago 360

Things to Do This Week

Don’t miss out on Chicago’s hottest events, festivals, new restaurant openings, and seasonal activities. Your weekly guide to what’s trending in the city—curated by locals.

See What’s Happening

What’s Happening in Chicago Now

Reader Favorites

Our most-loved Chicago guides

Hi, I’m Jill

I’ve lived in and around Chicago for over 10 years. I started Little Chicago Guide to share the city I love — beyond the Bean selfies and deep dish debates. You’ll find neighborhood secrets, local favorites, and honest recommendations from someone who actually lives here. No sponsored fluff, no tourist traps. I’ve shared Chicago travel tips on Fox 32 Chicago, Fox 17 West Michigan, and WDIV Detroit — and I’d love to help you plan your perfect trip.

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