A Local’s City Guide
Chicago, like a local shows you.
Neighborhood guides, seasonal events, hidden gems, and trip-ready itineraries — curated by a Chicagoan who actually lives here.
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.
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.
New on LittleChicagoGuide.com
Best Rooftop Bars in Chicago 2026: Skyline Views & Local Picks
Most Romantic Restaurants in Chicago (by Neighborhood)
25+ Best Chicago Summer Festivals 2026: Music, Food & Street Fairs Guide
Chicago Memorial Day Weekend 2026: A Local’s Guide
Obama Presidential Center: A Local’s Visitor Guide (2026)
Hidden Disney World Costs That Will Shock You (And How to Avoid Them in 2026)
Old Town Chicago: A First-Timer’s Complete Guide (2026)
How to Celebrate Martin Luther King Day in Chicago 2026: 20+ Events & Activities
Best Pizza in Chicago: A Guide to the Windy City’s Top Pies
Best Italian Food in Chicago’s Gold Coast
Best Things to Do with Kids in Lincoln Park, Chicago: A Family-Friendly Guide (2026)
20 Best Things to Do in Chicago for Halloween
Chicago New Year’s Eve Fireworks & Events: Ring in 2026 in Style!
Best St. Patrick’s Day Bars in Chicago 2026
Things to Do in Logan Square Chicago (2026 Neighborhood Guide)
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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