The Peninsula Chicago - Luxury Package
Sep 10 – Sep 144 nights
The Peninsula Chicago
The Peninsula Chicago
For out-of-towners who want a high-end hotel included with their trip.
5 Days in Chicago, 5 days, culinary and cultural journey
ChicagobyKellyRizzo
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.
5 days, 4 nightsSmall group experience
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
TravelwithKellyRizzo
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
A Culinary Adventure
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.
Insider Access
Kelly's own connections open doors: chef hellos, a private rooftop cocktail session, and tables that are nearly impossible to book on your own.
Iconic Chicago
A Cubs day game at Wrigley, an architecture cruise down the river, Cloud Gate, and late-night blues at Kingston Mines
Five-Star Home Base
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
OneClickIn.EverythingElseHandled.
From $4,150Sep 10, 2026 — Sep 14, 2026 · 5 days · 4 nights
double occupancy
Add $1,350 for single occupancy.
Highlights
SignatureMoments
Where You'll Stay
Choosewhereyou'llstay
Pick the home base for your trip — your investment updates to match.
Locals Package
For locals who want to join activities and sleep at home.
The Itinerary
5DayswithKellyRizzo
01
Thu, Sep 10
Settle In & Exclusive Dinner at Chicago's Finest
3 momentsGold Coast & Lakefront Stroll
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.
Check-in · The Peninsula Chicago
BOKA Progressive Dining (Girl and the Goat, Momotaro, + more!)
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!
02
Fri, Sep 11
Windy City Classics
6 momentsBreakfast — Beatrix Streeterville
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.
Chicago Architecture Boat Tour
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-Style Lunch — Portillo's
Chicago institution (char dog + Italian beef); handles big groups with ease. Casual, fast.
Millennium Park & Cloud Gate ('The Bean')
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.
Rooftop Happy Hour at Z Bar
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.
Dinner — Ema
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.
03
Sat, Sep 12
A Day at Wrigley!
5 momentsGame-Day Breakfast - Do-Rite Donuts & Chicken
A Chicagoland favorite serving small-batch donuts, crispy fried chicken, and crave-worthy comfort food across five locations.
Wrigleyville Pre-Game Exploration
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.
Chicago Cubs vs. Pittsburgh Pirates - Wrigley Field
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.
Dinner — Bacino's of Lincoln Park
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.
Kingston Mines Blues Club
Live Chicago blues across two stages, running late into the night. Loud, soulful, and about as Chicago as a nightcap gets.
04
Sun, Sep 13
Art Institute & High Tea at The Peninsula
6 momentsMorning Coffee — Ralph's Coffee
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.
The Art Institute of Chicago
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.
Free Time - Spa or Magnificent Mile Shopping
A little downtime before tea - the spa, pool, or last-minute shopping on Michigan Avenue.
Afternoon Tea at The Lobby — The Peninsula
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.
Included
Three Dots and a Dash Mixology & Cocktails
Slip down the hidden alley stairs into Chicago's favorite tiki hideaway for a pre-dinner round.
Farewell Dinner — RPM Italian
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.
05
Mon, Sep 14
Farewell & Check Out
2 momentsFarewell Breakfast at Pierrot Gourmet
One last gathering over coffee before goodbyes.
Check-out · The Peninsula Chicago
Investment
Investment
Sep 10 – Sep 14, 2026
The Peninsula Chicago - Luxury Package
$4,150
The Peninsula Chicago
+$1,350 single occupancy
For out-of-towners who want a high-end hotel included with their trip.
- 4 Nights of 2 Queens or 1 King depending on availability
- All included activities
Locals Package
$1,750
For locals who want to join activities and sleep at home.
- Everything except for a hotel.
$4,150
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
OneClickIn.EverythingElseHandled.
Reply to reserve your place. We will walk you through the details and hold your spot while you decide.
Reserve your placeWhat's Included
- 4 Nights of 2 Queens or 1 King depending on availability
- All included activities
- BOKA Progressive Dining (Girl and the Goat, Momotaro, + more!)
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!
- Breakfast — Beatrix Streeterville
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.
- Rooftop Happy Hour at Z Bar
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.
- Chicago Architecture Boat Tour
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-Style Lunch — Portillo's
Chicago institution (char dog + Italian beef); handles big groups with ease. Casual, fast.
- Millennium Park & Cloud Gate ('The Bean')
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.
- Dinner — Ema
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.
- Game-Day Breakfast - Do-Rite Donuts & Chicken
A Chicagoland favorite serving small-batch donuts, crispy fried chicken, and crave-worthy comfort food across five locations.
- Chicago Cubs vs. Pittsburgh Pirates - Wrigley Field
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.
- Dinner — Bacino's of Lincoln Park
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.
- Kingston Mines Blues Club
Live Chicago blues across two stages, running late into the night. Loud, soulful, and about as Chicago as a nightcap gets.
- Morning Coffee — Ralph's Coffee
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.
- The Art Institute of Chicago
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.
- Afternoon Tea at The Lobby — The Peninsula
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.
- Three Dots and a Dash Mixology & Cocktails
Slip down the hidden alley stairs into Chicago's favorite tiki hideaway for a pre-dinner round.
- Farewell Dinner — RPM Italian
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.
- Farewell Breakfast at Pierrot Gourmet
One last gathering over coffee before goodbyes.
What's Not Included
- Airfare
- Transportation (airport and inner-city transfers)
- Alcohol past welcome drinks
- Gold Coast & Lakefront Stroll
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.
- Wrigleyville Pre-Game Exploration
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.
- Free Time - Spa or Magnificent Mile Shopping
A little downtime before tea - the spa, pool, or last-minute shopping on Michigan Avenue.
Itinerary subject to change without notice.
Transportation
GettingAround
We handle the logistics so you can focus on the experience