I’m sharing my go-to Chicago finds — from late-night cheap eats and hidden coffee gems to the kind of date-night spots worth splurging on. Drop your email below and you’ll be first in line when the guide goes live.
Get on the Waitlist for the Chicago Travel Guide
My new travel guide is coming soon
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
This guide is designed to feel like a friend showing you around—not an algorithm spitting out the same old list.
By joining the waitlist, you’ll be the first to get early access and a few extra behind-the-scenes tips I won’t be sharing anywhere else.
Here’s just a taste of what you’ll find when the guide launches
My favorite splurge-worthy date-night spots (yes, cocktails included)
A weekend itinerary designed to feel local, not touristy
Late-night bites that feel like a secret—cheap, delicious, and only known by those in the know
A tucked-away park with skyline views (and hardly any crowds)
The neighborhood café that locals claim has the best cappuccino in the city
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