Chicago Cocktail Adventure Part 2

Imagine wandering through the heart of Chicago’s Loop, sipping on beautifully crafted cocktails, and soaking in the city’s storied past. This Chicago Cocktail Adventure Part 2 offers just that—a 3-hour, app-guided tour that takes you to some of the city’s most iconic cocktail spots, all within walking distance. For just $5 per person, it’s an affordable way to add a touch of sophistication to your visit, especially if you’re traveling solo or with a small group.

What makes this tour particularly appealing is the way it combines history, architecture, and mixology in a relaxed, flexible format. The tour is curated by Amy Bizzarri, author of “Chicago’s Iconic Dishes, Desserts, and Drinks,” so you’re guaranteed authentic insights and a taste of Chicago’s legendary drink scene. Plus, the app-based setup means you can start, pause, or revisit it at your own pace—perfect if you prefer a slow, savoring approach or want to spread it over several days.

Two features stand out: First, the visit to the Palmer House Hilton’s historic lobby for cocktails amid glamorous surroundings, and second, the chance to admire Chicago’s stunning architecture and landmarks like Millennium Park and the Art Institute of Chicago along the route. The free entry to historic sites and the flexible schedule are real pluses, although the tour itself doesn’t include drinks or food, so you’ll need to budget separately for your cocktails.

This adventure suits those who love a mix of history, urban exploration, and good drinks, especially if you enjoy discovering local legends and iconic spots at a leisurely pace. It’s ideal for grown-ups looking for a memorable, authentic Chicago experience that’s both educational and a little indulgent.

Key Points

• Affordable and flexible: Just $5 per person, with a self-guided format that fits your schedule.
• Historic venues and landmarks: Includes stops at iconic spots like the Palmer House Hilton and Macy’s.
• Great for architecture lovers: Enjoy views of Millennium Park, the Art Institute, and Chicago’s famous buildings.
• No drinks included: Budget for cocktails and snacks as you choose your favorites at each stop.
• Perfect for a laid-back, grown-up night out: Ideal for solo travelers or small groups wanting an authentic city experience.
• Tour is part of a series: Be sure to check out Part 1 for a complete Chicago cocktail experience.

A Detailed Look at the Chicago Cocktail Adventure Part 2

Starting Point: The Congress Plaza Hotel & Convention Center

The tour kicks off at the Congress Plaza Hotel on Michigan Avenue, a choice location that sets a grand tone. You’ll get your first taste of Chicago’s elegant hospitality history, and from here, the app guides you seamlessly to your next stop. The meeting point is convenient, close to public transportation, making it accessible whether you’re arriving by train, bus, or car.

Stop 1: Palmer House Hilton Historic Lobby

This is a highlight of the tour. The Palmer House Hilton’s lobby is a true Chicago landmark, filled with gilded ceilings, marble columns, and vintage glamour. As you sip your signature cocktail at the Lobby Bar, you’re not just enjoying a drink; you’re enjoying the hotel’s legendary past, which has hosted everyone from royalty to Hollywood stars. The app provides commentary on the hotel’s architecture and its famous guests, lending a layer of sophistication to the experience.

According to reviews, visitors appreciate the elegance and history here. One user notes, “The Lobby Bar is beautiful, and having a cocktail in such a historic setting makes you feel like part of Chicago’s high society.” It’s a perfect spot to slow down and appreciate the city’s storied past while savoring a well-crafted drink.

Stop 2: Macy’s on State Street

Next, you stroll through the historic Macy’s, formerly known as Marshall Field’s, a store that’s been part of Chicago’s retail fabric for over a century. You’ll head to the Walnut Room on the 7th floor, famous for its ornate architecture and iconic ceiling. The tour recommends a signature Chicago cocktail here, though you’re free to pick any drink you like.

This stop gives you a taste of Chicago’s retail history combined with a chance to enjoy a classic cocktail. Reviewers mention the “famous Walnut Room” and how the vintage ambiance complements the drink experience. It’s an easy walk, and the lively atmosphere of Macy’s adds to the fun.

Stop 3: Carbide and Carbon Building

A true architectural gem, the Carbide and Carbon Building is a stunning example of Art Deco design. The tour takes you inside for a glass of champagne at Venteux, which offers a sophisticated setting to continue your journey. From the outside, the building’s sleek black and gold façade is an Instagram-worthy sight, and inside, you’ll enjoy a luxurious ambiance.

The reviews rave about the building’s beauty. One said, “Seeing this landmark up close and inside with a glass of bubbly was a highlight of our Chicago trip.” It’s a moment that combines visual grandeur with a little bubbly—hard to beat.

Scenic Walks and Photo Opportunities

Between stops, you’ll walk along the edge of Millennium Park, giving you chances to snap photos of the Cloud Gate (the Bean), the Jay Pritzker Pavilion, and the artistic skyline. The route also takes you past the Art Institute of Chicago, where you can catch a glimpse of the famous stone lions—a quick photo op that’s worth the detour.

These scenic strolls are what make this tour stand out. The app provides guidance, but you can take your time exploring. Many reviewers enjoy the combination of urban sights and historic buildings, with one noting, “The views of Millennium Park and the Art Institute are stunning, and it’s all within easy walking distance.”

End Point: Virgin Hotels Chicago at Cerise

Your tour wraps up at the Virgin Hotels’ rooftop bar, Cerise, located at the top of the hotel. Here, you can toast your Chicago evening while overlooking the city skyline. The view from above offers a fitting finale to your cocktail adventure, giving you a panoramic perspective of Chicago’s architectural marvels.

What Travelers Can Expect

Ease and Flexibility

Since the entire experience is app-guided, you control the pace. You can pause, restart, or even split the tour over several days—making it suitable for those with tight schedules or who prefer a leisurely exploration. The GPS directions ensure you won’t get lost, even if you veer off course to enjoy an unexpected view or pick up a souvenir.

Atmosphere and Authenticity

The stops are carefully chosen for their historic significance and architectural beauty, not just their cocktails. This makes the tour appealing for those who want more than just a drinking spree; it’s about learning stories, appreciating design, and experiencing Chicago’s vibrant history. The fact that all stops are free to enter means you’re not paying extra for admittance, just for your drinks.

Cost and Value

At $5 per person, the tour is remarkably inexpensive, especially considering the high-quality venues and the curated experience. Remember, drinks and food are not included, so budget accordingly—expect to pay separately for each cocktail. But the value comes from the combination of entertainment, education, and scenic walks.

Potential Drawbacks

Some travelers might find the lack of included drinks a slight downside, but it also allows flexibility—you’re free to choose your favorite cocktails or keep it simple with just a glass of champagne. Also, because it’s a self-guided tour, groups looking for guided commentary or more interaction might prefer a traditional guided tour.

Who Should Consider This Tour?

This experience is best suited for adults who enjoy a leisurely blend of history, architecture, and good drinks. It’s perfect for those looking for a low-cost, relaxed way to explore downtown Chicago while savoring its iconic cocktails. If you’re traveling solo or with a small group, you’ll find this flexible format ideal. It also suits those who love photo opportunities and urban strolls, especially along Millennium Park and the Art Institute.

Final Thoughts

The Chicago Cocktail Adventure Part 2 offers an engaging mix of historic venues, beautiful architecture, and scenic city walks. Its app-guided format makes it flexible and easy to follow, while the curated stops ensure you’re experiencing some of Chicago’s most iconic bars and landmarks. For just a few dollars, you get a taste of the city’s glamorous past and lively present, all at your own pace.

While it doesn’t include drinks, that’s part of the charm—allowing you to choose your own cocktails and enjoy them in historic settings. It’s a great way to add some sophistication to your Chicago visit without breaking the bank. If you’re a fan of architecture, history, and a well-made cocktail, this tour is worth considering.

FAQ

Is this tour suitable for children or those under 21?
No, the tour involves alcohol consumption, so participants must be 21 or older and prepared to show ID.

Can I do this tour over multiple days?
Yes, since it’s app-guided and flexible, you can start, stop, and spread the stops out over several days if you prefer.

Are drinks included in the price?
No, the $5 fee covers the app-guided experience. Drinks and food are purchased separately at each stop.

What is the walking distance like?
All stops are within an easy walk in the downtown area, along Millennium Park and the Loop.

What if I want to skip a stop or change the order?
The app allows you to navigate at your own pace, so you can skip, revisit, or re-arrange stops as you like.

How long does the tour take?
Approximately 3 hours, but you can extend or shorten it based on your pace and interest.

Where does the tour end?
It concludes at the Virgin Hotels Chicago rooftop bar, Cerise, offering a stunning city view.

Is the tour accessible for those with mobility issues?
Since all stops are on foot within the downtown area, accessible arrangements depend on personal mobility needs—check the locations for specific accessibility info.

Do I need to book in advance?
While walk-ins are possible, it’s recommended to book about 32 days in advance to secure your spot and access the full experience.

What should I bring?
Bring your ID for age verification, a smartphone with the eATLAS app, and some cash or card for drinks and snacks.

To sum it up, the Chicago Cocktail Adventure Part 2 is a budget-friendly, flexible, and authentic way to experience the city’s historic bars, iconic architecture, and scenic vistas. It suits those who enjoy a mix of learning, sightseeing, and sipping—without the fuss of guided tours or fixed schedules. Whether you’re a cocktail enthusiast, history buff, or simply want to enjoy Chicago from a different perspective, this tour offers a delightful and approachable outing.