Chicago Cocktail Adventure Part 1

Looking for an entertaining way to experience Chicago’s lively bar scene without breaking the bank? The Chicago Cocktail Adventure Part 1 offers a relaxed, self-paced journey through some of the city’s most iconic cocktail venues, all while soaking in the stunning architecture and vibrant energy of the Loop. Curated by Amy Bizzarri, author of “Chicago’s Iconic Dishes, Desserts, and Drinks,” this tour promises a mix of history, architecture, and great drinks—perfect for an adult night out or a spontaneous adventure.

What’s particularly appealing? First, the flexibility of an app-guided experience that you control—start, pause, or spread out across several days. Second, the chance to savor beautiful city views from a rooftop bar and walk past Chicago’s architectural marvels. On the flip side, this tour isn’t about included drinks or food, so you’ll want to budget for your preferred cocktails. It’s best suited for travelers who enjoy discovering local stories, appreciate good architecture, and love a well-crafted cocktail.

Key Points

• Self-guided flexibility allows you to set your own pace and extend the experience over multiple days.
• Stunning views and architecture provide a scenic backdrop for your drinks and walk.
• Affordable price point ($5 per person) makes this a budget-friendly way to explore Chicago’s bar scene.
• All stops are within walking distance in the heart of downtown, making it easy to follow.
• No included drinks, so you can choose what appeals most at each stop.
• A mix of history, design, and mixology offers a well-rounded city experience.

The Chicago Cocktail Adventure Part 1 is designed for adults who love a blend of history, architecture, and a good drink. It’s not a traditional guided tour with a tour guide and group; rather, it’s a self-led exploration via the eATLAS app. For $5, you gain access to a series of stops that weave together Chicago’s drinking culture with its iconic sights.

This tour is particularly appealing for those who prefer a more relaxed, flexible itinerary. You can start at the designated meeting point, the LondonHouse Chicago, and follow the app’s GPS to each stop, pausing or returning whenever you like. The entire route takes about three hours, but you might find yourself lingering longer at certain spots, especially if you’re enjoying the views or trying a favorite cocktail.

The route begins with a visit to the LondonHouse’s rooftop bar—an excellent way to start with cityscape views and a stylish setting. From there, the walk takes you along Millennium Park’s edge, offering views of the Crown Fountain—a fun photo op and a chance to soak in Chicago’s modern art scene.

The last stop, nestled near the Harold Washington Library, offers a chance to admire Chicago’s architecture up close, including a look at the historic Monadnock Building. The entire route is within easy walking distance, making this tour very accessible for most travelers.

The Stops and Their Charm

LondonHouse Chicago is a stellar first stop. Its rooftop bar isn’t just about the drinks but the spectacular views of the skyline. We loved the way the tour sets a stylish tone right from the start, giving you a taste of Chicago’s upscale side. The free access to the app’s “Sip History” feature adds a layer of insight into each location’s background, enriching the experience beyond just the drinks.

Next, strolling along Millennium Park’s edges, you’ll get a brief taste of the city’s urban beauty, with the Crown Fountain nearby providing a playful visual contrast to the sleek cityscape. The walk itself is part of the charm—encouraging you to take in the architecture and vibrant energy of downtown Chicago.

The final stop near Harold Washington Library offers a quieter moment, with impressive architecture to admire, complemented by the historical surroundings of the Monadnock Building. This stop is a reminder of Chicago’s long-standing architectural influence—definitely worth a look if you love design.

The last stop, Brando’s Speakeasy, completes the evening with a nod to Chicago’s Prohibition-era roots. Although the tour recommends specific drinks, the freedom to choose your favorite cocktail makes it feel personalized. One traveler commented, “None of the three places we went to had the signature drinks recommended, but we enjoyed ordering from the menu just the same.” This flexibility is key if menu updates or seasonal changes happen.

What This Tour Means for You

The value of this experience lies in its combination of affordability and flexibility. For just a few dollars, you get an enjoyable guided map that helps you explore at your own pace, with plenty of opportunities to pause and savor. It’s perfect for travelers who like a bit of independence but still want a curated experience.

The cost of drinks and food is not included, which could be seen as a drawback but also as an advantage—giving you control over what you spend and drink. The recommended drinks provide a starting point if you’re unsure what to order, but the freedom to pick something different is a nice touch.

In terms of value, this tour offers a quick yet rich taste of Chicago’s bar scene and architectural beauty, making it a good option for a last-minute plan or a lighthearted evening. However, keep in mind that the drink recommendations may sometimes be outdated—one reviewer noted that some signature drinks no longer appeared on menus, but they still enjoyed the experience overall.

Who This Tour Is Best For

This experience is ideal for mature travelers who enjoy a mix of history, design, and cocktails. It’s a great pick for solo visitors, couples, or small groups who want a flexible, low-cost outing. Those interested in Chicago’s architecture and visual scenery will find the walk especially rewarding.

If you prefer guided tours with a group or include drinks in the ticket price, this might not be your best fit. But if you’re happy to explore at your own pace and enjoy city views from rooftops, this tour hits the right notes.

The Chicago Cocktail Adventure Part 1 offers a smart way to blend history, architecture, and good drinks into one relaxing, flexible experience. The tour’s app-guided format allows you to craft your pace, whether you prefer to savor each stop or spread out the adventure over multiple days. It’s a budget-friendly way to explore some of Chicago’s most iconic cocktail venues and architectural sights in the heart of downtown.

What makes this tour stand out is the opportunity to enjoy stunning city views and walk past historic buildings like the Monadnock, all while sampling or simply observing Chicago’s vibrant cocktail scene. It’s especially suitable for travelers who appreciate a laid-back, self-directed experience with a touch of sophistication.

While not including drinks or food, the flexibility and scenic settings make this a compelling choice for anyone looking for an authentic, grown-up night out in Chicago. Whether you’re a solo wanderer or part of a couple seeking a memorable evening, this tour offers a taste of the city’s lively spirit through its drinks, sights, and stories.

Is this a guided tour with a guide?
No, it’s an app-guided experience you control. There’s no live guide, so you can start, stop, and spread the tour out as you like.

How much does it cost?
The tour fee is $5 per person, making it very affordable. Remember, drinks and food are extra.

Where does the tour start and end?
It begins at LondonHouse Chicago, and the last stop is Brando’s Speakeasy on South Dearborn Street.

How long does the tour take?
Approximately three hours, but you can extend or shorten it based on how long you linger.

Are drinks included?
No, the cost of drinks and snacks is not included. You’re free to choose your preferred cocktails at each stop.

Can I do this tour over multiple days?
Yes, the app’s flexibility allows you to break the experience up into several sessions, which some travelers find convenient.

Is this suitable for all ages?
The drinking age is 21+, so be ready to show ID if you plan to sip.

What’s the best part of the tour?
Many enjoy the stunning views from the rooftop bar and the walk past historic architecture, like the Monadnock Building.

Is the experience family-friendly?
It’s tailored for adults interested in cocktails and architecture, so it’s best suited for those over 21 who enjoy a grown-up outing.

In all, the Chicago Cocktail Adventure Part 1 offers a unique blend of scenery, history, and well-crafted cocktails that make for a memorable night or a leisurely exploration of the city’s vibrant drinking culture.