If you’ve ever finished a trip wishing you’d seen more of the real city instead of the tourist version — this guide was made for you.
Planning a trip to Chicago usually starts the same way: hours of Googling, scrolling TripAdvisor lists, or falling down TikTok rabbit holes. You end up with the same recommendations everyone else has — Millennium Park, Navy Pier, deep-dish from the most overhyped spot in town. By the time you arrive, you’re following a script instead of actually experiencing the city.
And here’s the truth: those guides aren’t wrong, but they’re not the Chicago locals love. They won’t show you the cozy coffee counter that makes your morning feel like home, the taco stand that locals line up for at midnight, or the neighborhood stroll that opens the city up in a whole new way.
Most Chicago Travel Guides Leave You Feeling Stuck and Overwhelmed
Slowly, intentionally, and with room for surprises. It’s not a list of 200 “must-sees.” It’s a curated map of experiences that make Chicago feel alive: coffee shops, bookstores, late-night eats, wine bars, green spaces, and all the places that don’t show up on the first page of Google.
This guide shows you how to move through the city like you belong here. Whether it’s your first trip or your fifth, you’ll come home with stories that feel like your own.
The Chicago Travel Guide is designed to help you experience the city the way I do
A Chicago Travel Guide That Feels Like a Friend
Personal Notes & Memory Prompts — little nudges to help you notice the details that will stick with you long after you leave
Weekend-Ready Itineraries — flexible day plans that make exploring easy without feeling rushed
Quiet Green Spaces & Scenic Views — tucked-away parks and skyline overlooks for when you need to slow down
Date-Night Worthy Dinners — cozy wine bars, intimate restaurants, and splurge-worthy spots that feel special
Cheap Eats with Big Flavor — taco joints, pizza slices, and hole-in-the-wall favorites
Neighborhood Walks & Hidden Corners — curated strolls through areas most tourists never see
Morning Coffee & Bakeries — where to start your day with the best cappuccinos, pastries, and neighborhood vibes
- Curated, not crowded. Only the places worth your time make the cut.
- Lived-in, not listicles. These are the places I go, not the ones optimized for clicks.
- Designed for connection. It’s less about “seeing everything” and more about creating moments that feel like yours.
This guide saves you time, helps you avoid tourist fatigue, and gives you the confidence to explore Chicago like you already know your way around.
Why my Chicago Travel Guide is Different
My guides are created for curious travelers who crave authenticity—those who’d rather wander through neighborhood cafés than crowded chains, browse family-run shops instead of souvenir stands, and discover hidden corners that don’t make it onto mainstream lists.
Each guide blends practical tips with thoughtful storytelling, giving you the kind of insider perspective that helps you feel at home in a new city. Whether you’re looking for the coziest spot to grab coffee, a tucked-away park where locals unwind, or cultural traditions you won’t find in guidebooks, I make sure you leave with memories that feel lived-in, not manufactured.
Traveling shouldn’t just be about checking boxes—it should be about connection, immersion, and feeling like you belong.
I make travel guides for people who don't want to experience a city like a tourist
Meet Jenna
Because those lists are crowded, outdated, and don’t give you context. This guide is curated, lived-in, and designed to make your trip feel like your own story.
Why not just use Google or TripAdvisor?
Absolutely. It gives you the essentials without overwhelming you, while also showing you spots even repeat visitors rarely find.
Is this good for first-time visitors?
The Chicago Travel Guide is digital, designed to be easy to use on your phone while you’re on the go.
Is it digital or printed?
Right after purchase. You’ll get an email with your download link so you can dive in right away.
When will I get the guide?
We've Got the Answers
Have Questions?
Chicago is more than its skyline and deep-dish pizza. It’s the quiet mornings in neighborhood cafés, the unexpected side streets that draw you in, the dinners that linger, and the moments you’ll talk about long after you’ve gone home.
travelled using the paris guide
Isabel C.
"We still laugh about the night we ended up in that hole-in-the-wall jazz bar Jenna recommended. It wasn’t on any list we found online, but it became the absolute highlight of our trip."
travelled using the asheville guide
MARCIA F.
"Instead of a generic rooftop bar, Jenna pointed us to a tucked-away wine bar where we met two sisters celebrating a birthday. We ended up joining their table, sharing a bottle, and now we text them every week. That never would’ve happened with a regular tourist guide."
travelled using the nyc guide
Caroline M.
"Jenna’s guide led us to this tiny bakery in Lincoln Square where we ended up chatting with the owner for half an hour. We still dream about the pistachio croissants — it felt like we stumbled into someone’s home kitchen."
WHAT TRAVELERS ARE SAYING