5 Days in Chicago, 5 days, culinary and cultural journey
Five days in Chicago (Sept 10-14) with Kelly Rizzo experiencing the best of the city - from a Girl & the Goat welcome dinner and deep dish to a Cubs day game at Wrigley, rooftop cocktails, live blues, and afternoon tea at The Peninsula.
The Trip
A five-day, four-night city retreat with Kelly Rizzo, based at The Peninsula Chicago (Sept 10-14). We eat our way through Kelly's Chicago - a Girl & the Goat welcome dinner, Portillo's, and her favorite deep dish - build in an architecture cruise on the river, a private Z Bar rooftop cocktail session at golden hour, a Saturday Cubs day game at Wrigley, and live blues at Kingston Mines, then close with the Peninsula's celebrated afternoon tea and a River North farewell dinner. Small group, insider access, and Kelly's own connections opening doors along the way.
Your Host
Kelly Rizzo is a born-and-raised Chicagoan and the creator behind Eat Travel Rock, the award-winning platform where she's spent years taking her audience behind the scenes with the chefs, restaurants, and hidden gems that make a city worth the trip. Through her Eat Travel Rock TV series and her podcast Comfort Food, she's built a following of nearly 900,000 by championing the places she genuinely loves. Now she's bringing it all home: five days in the city that shaped her, built around her favorite activities and eats.
Kelly Rizzo
Trip Host & Creator
Eat your way through Kelly's Chicago: a Girl & the Goat welcome dinner, her favorite deep dish, a Portillo's char dog, and a glossy River North farewell.
Kelly's own connections open doors: chef hellos, a private rooftop cocktail session, and tables that are nearly impossible to book on your own.
A Cubs day game at Wrigley, an architecture cruise down the river, Cloud Gate, and late-night blues at Kingston Mines
Four nights at The Peninsula Chicago on the Magnificent Mile, home to its celebrated afternoon tea, the rooftop Z Bar, and a 19th-floor pool.
Four nights at The Peninsula, curated dinners at Kelly's favorite tables, a Cubs day game, the river cruise, rooftop cocktails, and afternoon tea, with a Byline concierge handling every detail. You just show up hungry.
Reserve
double occupancy per traveler
Highlights
Where You'll Stay
Carefully chosen for an unforgettable stay
Home base: The Peninsula Chicago on Superior Street, steps off the Magnificent Mile. Four nights (check-in Thu Sept 10, checkout Mon Sept 14). The 19th-floor pool + sun terrace and 24-hr fitness are complimentary for guests. Spa appointments available upon request.
The Itinerary
Investment
per traveler · all hosted experiences included
Sep 10 – Sep 14, 2026 · 4 nights
Secure your spot with a $500 refundable deposit
Add $1,350 for single occupancy.
Influencer Experiences
What's Included
Stretch your legs with an easy stroll through the historic Gold Coast to Oak Street Beach, skyline on one side, Lake Michigan on the other.
What's Not Included
Reserve
Reply to reserve your place. We will walk you through the details and hold your spot while you decide.
Reserve your placeTransportation
We handle the logistics so you can focus on the experience
