A Local’s City Guide
Chicago… let a local show you.
Neighborhood guides, seasonal events, hidden gems, and trip-ready itineraries — curated by a Chicagoan who actually lives here.
Updated every Sunday
What’s on in Chicago this week
September 21 to September 27, checked by hand on September 22
Neighborhoods
Choose your Chicago.
Every neighborhood has its own accent. Start with one of these, then explore the rest of the city block by block.
Weekend Guide
The Perfect Chicago Weekend
Two days, three meals, one skyline view you won’t forget — the exact itinerary I share with every friend who visits.
Read the guide →Latest Stories
From the magazine.
Food · 6 min
Where Locals Actually Eat Deep Dish
Skip the chains. The pizzerias Chicagoans defend like family — and what to order at each.
First-Timer · 12 min
Best Things to Do in Chicago
The first-timer’s complete guide — the icons, the sleepers, and how to see them without the crowds.
Nightlife · 10 min
15 Best Chicago Speakeasies & Hidden Bars
Behind the unmarked doors — the cocktail rooms locals keep to themselves.
Experience Fall in Chicago
Explore Chicago By Neighborhood
Chicago is really a collection of neighborhoods, each with its own personality — and the best way to find your kind of trip is to start with the map. Tap any neighborhood to dig into where to eat, drink, and explore, from Andersonville up north to Pilsen and the South Loop.
23 Best Places to Celebrate St. Patrick’s Day in Chicago (2026 Guide)
Best Chicago Neighborhoods to Visit (by What You Want to Do)
12 Best Things to Do in Andersonville, Chicago (2026 Local Guide)
Best Christmas Tree Farms Near Chicago: Cut Your Own Tree Guide
Best Vegan Bakeries in Chicago: 10 Amazing Spots for Plant-Based Treats (2026)
Hyde Park Chicago: 13 Best Things to Do
Chicago Riverwalk Restaurants: Best Places to Eat with Food, Views & Vibes
The Marshall Field’s Walnut Room: A Chicago Holiday Guide
Best Downtown Chicago Hotels 2026: Luxury, Boutique & Budget by Neighborhood
We Map the Best of Chicago
We don’t just list Chicago’s best spots — we pin them. Every guide comes with a neighborhood map, so you can find what’s nearest you or your hotel instead of scrolling a list. Our rooftop bar map is a good place to start: skyline lounges downtown, local beer gardens up north, each pinned and ready to explore.
Hi, I’m your guide
Chicago is my hometown — and my favorite story to tell.
I’ve spent more than a decade exploring every block of this city — and sharing it on Fox 32 Chicago, Fox 17 West Michigan, and WDIV Detroit. Little Chicago Guide is everything I’d tell a friend before her first visit: neighborhood secrets, honest restaurant picks, and the parts of Chicago that aren’t on the postcards. No sponsored fluff, no tourist traps.
About the guide →The Sunday Letter
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