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
Add $1,350 for single occupancy.
Highlights
Where You'll Stay
Pick the home base for your trip — your investment updates to match.
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.
What’s included
Not included
The Itinerary
Investment
Sep 10 – Sep 14, 2026
$4,150
+$1,350 single occupancy
For out-of-towners who want a high-end hotel included with their trip.
$1,750
For locals who want to join activities and sleep at home.
per traveler · all hosted experiences included
Sep 10 – Sep 14, 2026 · 4 nights
No card needed. Apply today.
Add $1,350 for single occupancy.
Reserve
Reply to reserve your place. We will walk you through the details and hold your spot while you decide.
Reserve your placeWhat's Included
A one-of-a-kind progressive dining experience through Chicago's Fulton Market, featuring standout stops like Girl & the Goat and Momotaro. Guests will enjoy multiple courses across a curated, exclusive lineup of acclaimed restaurants, with the evening designed to feel exclusive, social, and distinctly Chicago. Select stops may also include special touches like premium cocktail or chef-led moments. Come hungry!
A relaxed group breakfast at Beatrix, an easy five-minute walk from the hotel. Think fresh, feel-good plates and great coffee to fuel the day ahead.
A private rooftop hour at The Peninsula's Z Bar, sipping craft cocktails from their experienced bar staff with Michigan Avenue skyline glowing at golden hour.
Ninety minutes on the water with expert guides telling the story of the city, building by building. It's widely considered the best way to see Chicago, and the skyline views from the river are hard to beat.
Chicago institution (char dog + Italian beef); handles big groups with ease. Casual, fast.
A stop at Millennium Park for the classic photo at Cloud Gate, better known as The Bean. Take your time, get your shots, and loop through the park at your own pace.
Tonight we walk over to Ema in River North, chef CJ Jacobson's bright, sun-soaked take on Mediterranean cooking. Think hummus and spreads, wood-grilled kebabs, and a table full of small plates made for sharing. Light, fresh, and easy to linger over.
A Chicagoland favorite serving small-batch donuts, crispy fried chicken, and crave-worthy comfort food across five locations.
An afternoon in the friendly confines of one of baseball's cathedrals, and a Kelly must for any Chicago weekend. Grab a beer, catch some sun, and take in a day game at Wrigley.
Tonight is all about Chicago's signature dish: deep dish, in the form of Bacino's legendary stuffed pizza, one of Kelly's longtime favorites. It's rich, golden, and satisfyingly over-the-top. Bring your appetite.
Live Chicago blues across two stages, running late into the night. Loud, soulful, and about as Chicago as a nightcap gets.
An easy morning coffee at Ralph's, tucked inside the Ralph Lauren flagship on Michigan Avenue. Grab a perfect espresso and a pastry in one of the most charming little cafés in town, just a couple of minutes from the hotel.
For the art lovers, one of the world's great museums, home to Impressionist masterpieces and American Gothic. Wander at your own speed and see as much or as little as you like.
The city's most celebrated afternoon tea, served in The Lobby with champagne and a seasonal fall menu. It's elegant and unhurried, the kind of afternoon meant to be savored. A Chicago classic done at the highest level.
Slip down the hidden alley stairs into Chicago's favorite tiki hideaway for a pre-dinner round.
We're closing things out at one of River North's most stylish rooms, all marble and mood lighting. The menu leans into handmade pastas and classic Italian done well, with plenty to toast over. A memorable last night together.
One last gathering over coffee before goodbyes.
What's Not 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.
Soak up the pre-game buzz around Clark and Addison. The historic marquee, the bars, and the electricity of a ballpark neighborhood on game day.
A little downtime before tea - the spa, pool, or last-minute shopping on Michigan Avenue.
Transportation
We handle the logistics so you can focus on the experience
