Chicago: Where Great American Stories Meet Lakeside Luxury

Walk the Chicago Riverwalk

My favorite way to start the day in Chicago is with a walk along the river. The Chicago Riverwalk offers one of the best introductions to the city. As you stroll along the water, you'll pass architectural icons, public art installations, and lively outdoor cafés while gaining a deeper appreciation for the city's remarkable transformation following the Great Chicago Fire.

Lunch at Cindy’s Rooftop

With sweeping views of Millennium Park and Lake Michigan, Cindy's Rooftop is as much about the scenery as the food. The menu features fresh, approachable dishes that pair perfectly with a leisurely afternoon. Cindy’s gets very busy and it’s worth making reservations, regardless of the time of day.

Chicago architecture river cruise

Few experiences capture Chicago's story better than an architecture cruise. Expert guides explain how visionary architects transformed a city devastated by fire into a global center of design and innovation. Many tour companies also offer an evening cruise, but I find that those focus less on the architecture of the city.

Cocktails at LondonHouse Rooftop

Perched above the Chicago River, LondonHouse offers some of the city's most spectacular skyline views. Arrive before sunset to watch the buildings illuminate as day turns to night.

Dinner at RPM Seafood

Located directly on the riverfront, RPM Seafood highlights fresh seafood and refined service. Floor-to-ceiling windows showcase the skyline and create a memorable dining experience.

Evening stroll through Millennium Park

After dinner, take a leisurely walk through Millennium Park and along Michigan Avenue. The city feels entirely different after dark, with illuminated architecture creating a dramatic backdrop for your first evening.

Guided food tour

Chicago's food scene tells the story of generations of immigrants who helped shape the city. Through neighborhood restaurants, local specialties, and family-owned businesses, you'll discover how food became one of Chicago's most powerful forms of storytelling. This is my top recommendation for Chicago and is a must-do!

Explore Chicago's historic neighborhoods

Neighborhoods like the West Loop, Fulton Market, and Pilsen each reveal a different chapter of Chicago's evolution. From industrial roots to culinary innovation, these areas showcase the city's remarkable ability to reinvent itself while preserving its character.

Drinks at Three Dots and a Dash

Hidden behind an unassuming entrance, this award-winning tiki bar transports guests to another world. The immersive atmosphere and inventive cocktails create a memorable conclusion to the evening. My favorite is the Pearl Diver! If you come with a group, try one of their large-format cocktails.

Dinner at Bavette's Bar & Boeuf

Inspired by classic steakhouses, Bavette's combines old-world charm with exceptional cuisine. Dim lighting, vintage décor, and attentive service create an atmosphere that feels timeless.

Explore the Loop

The Loop is where Chicago's architectural story comes to life. Walking among these historic skyscrapers offers a firsthand look at the innovations that forever changed urban design.

Excursion to Oak Park

Architecture enthusiasts may wish to visit the home and studio of Frank Lloyd Wright. The neighborhood contains one of the largest collections of Wright-designed buildings anywhere in the world and provides insight into his revolutionary ideas.

Lunch at The Berghoff

Opened in 1898, The Berghoff remains one of Chicago's oldest continuously operating restaurants. Its rich history and classic German-inspired cuisine offer a connection to the city's immigrant roots. I can never resist the Bavarian pretzel and housemade root beer.

Tour of Wrigley Field

More than just a baseball stadium, Wrigley Field is a living piece of American history. The behind-the-scenes tour provides access to areas normally reserved for players while sharing stories that span more than a century of baseball tradition. If the Cubs are in town, stay for a game. It’s a truly unique experience!

Explore Wrigleyville

The neighborhood surrounding the ballpark buzzes with energy year-round. Sports bars, local shops, and historic landmarks make it worth exploring even when the Cubs aren't playing. Sluggers is my go-to choice for a pint!

Lakefront walk along Lake Michigan

Chicago's relationship with Lake Michigan is central to its identity. Walking the shoreline provides a peaceful contrast to the city's bustling downtown while offering some of the best skyline views anywhere in the country.

Brunch at North Pond

Located inside a historic building overlooking a tranquil pond, North Pond feels surprisingly secluded despite its urban setting. Seasonal ingredients and exceptional service make it one of Chicago's premier brunch destinations.

Explore Lincoln Park or the Gold Coast

These neighborhoods showcase a different side of Chicago, one defined by elegant homes, tree-lined streets, and charming local businesses. It's the perfect opportunity to slow down and experience everyday life in the city.

Cocktails and Prohibition stories

Chicago's history is inseparable from the Prohibition era. Historic cocktail bars throughout the city preserve the stories of gangsters, speakeasies, and the colorful characters who helped shape Chicago's nightlife culture.

Live jazz at the Green Mill Cocktail Lounge

One of the country's most famous jazz venues, the Green Mill has welcomed musicians and patrons for more than a century. The intimate setting and rich history create an unforgettable evening that feels distinctly Chicago.

Dinner at Girl & The Goat

Bold flavors, inventive dishes, and a lively atmosphere have made Girl & The Goat one of the city's most celebrated restaurants. It's a fitting final chapter to a weekend defined by great stories and unforgettable meals. I love making a meal out of the small plates: the goat empanadas and chickpea fritters are my favorites!