Chicago Cocktail Adventure Part 1

If you’re craving a grown-up night out that combines history, architecture, and great cocktails without breaking the bank, the Chicago Cocktail Adventure Part 1 might just be perfect. For only $5 per person, you get a three-hour, self-paced tour that takes you through some of Chicago’s most iconic bars and landmarks. Led by Amy Bizzarri, author of “Chicago’s Iconic Dishes, Desserts, and Drinks,” this tour offers a uniquely local perspective on the Windy City’s drink culture, with a sprinkle of architectural sights thrown in.

What we love about this experience is its flexibility—it’s app-guided, so you can start, pause, and resume whenever it suits you. Whether you want to extend your visit at a favorite stop or split the tour over several days, this format adapts to your pace. The stops are all within walking distance in central Chicago, from the Millennium Park area to the Harold Washington Library. Plus, the stunning views of the city skyline from the rooftop bar at LondonHouse are genuinely memorable.

A possible consideration is that food and drinks are not included in the ticket price, so you’ll need to budget for those separately. Also, the tour involves some walking, so comfortable shoes are recommended. This experience is best suited for adults who enjoy exploring at their own pace, appreciate architecture and history, and love discovering local cocktail spots.

Key Points

• Flexible self-guided format allows you to start, stop, and rejoin at your convenience.
• Includes access to the eATLAS app with maps and GPS, making navigation easy.
• Stunning city views from the rooftop bar at LondonHouse make for memorable photo opportunities.
• The stops are all within easy walking distance, making it accessible and low-stress.
• Cost-effective at just $5, excluding drinks and food, giving you control over your spending.
• Suitable for anyone interested in Chicago’s architecture, history, and cocktail scene.

The Chicago Cocktail Adventure Part 1 is a charming way to explore the city’s vibrant bar scene without the hassle or expense of traditional tours. For just $5, you gain access to an app-guided experience that highlights six carefully curated stops in the heart of downtown Chicago, blending history, architecture, and libations.

Starting Point: LondonHouse Chicago

Your journey kicks off at the LondonHouse Hotel, a striking building on East Wacker Drive. Here, you’ll enjoy a rooftop bar experience with sweeping views of the Chicago skyline and Millennium Park. The rooftop is an ideal spot to start soaking in the city’s vibe, and the free admission to this part of the tour allows you to settle in with a drink and look beyond the horizon.

The view of Millennium Park and the Crown Fountain from here is particularly noteworthy, offering a scenic backdrop before you move on to explore the city’s architectural gems and historic venues. This stop sets the tone for a leisurely, scenic walk through downtown.

Walking Along Millennium Park and the Loop

As you stroll between stops, you’ll pass iconic landmarks like Millennium Park, the famous Crown Fountain, and the Harold Washington Library. These sites not only add visual interest but also give you a sense of Chicago’s blend of innovation and tradition. The architecture here is worth paying attention to, especially nearby historic buildings like the Monadnock Building, which you’ll pass right across the street from your last stop.

Stops and Drinking Venues

The tour is designed to highlight Chicago’s historic cocktail hotspots—places that have played a role in shaping the city’s drinking culture. While the specific drinks recommended (like the signature Giggle Water at the Motor Club) might sometimes be unavailable due to seasonal or menu changes, the tour offers the flexibility to order other items from the menu.

LondonHouse Rooftop Bar

The first stop at LondonHouse is a highlight, chiefly for its gorgeous city views. We loved the way this elevated setting frames the Chicago skyline, making it not just a bar but an experience. This stop provides a great photo op and an opportunity to enjoy a drink in a chic setting, all while being immersed in the city’s architectural grandeur.

The Final Stop: Brando’s Speakeasy

Your last stop is Brando’s Speakeasy on South Dearborn, which, true to its name, evokes the spirit of Prohibition-era Chicago. It’s a cozy spot that offers a sense of stepping back in time, perfect for ending the tour on a high note. The walk between stops is scenic, especially as you pass the Harold Washington Library, famed for its impressive architecture.

Feedback from past participants highlights a few key points. One reviewer, Cassandra, gave a four-star rating, mentioning that the tour’s drink recommendations needed updating but appreciated that they could order from the menu instead. She noted, “None of the three places we went to had the signature drinks that was recommended by Viator,” which is a reminder that menus can change, but the overall experience remains worthwhile.

Another traveler appreciated the stunning views at LondonHouse, emphasizing that the rooftop is a real ‘wow’ moment. The flexibility to break the tour into parts was also a plus, making this a good choice for travelers who prefer a relaxed pace or are short on time.

• The cost of the tour is very accessible, mainly because food and drinks are separate, giving you control over your spending.
• The duration of about three hours means you can enjoy it leisurely without feeling rushed, or spread it out over several days.
• The app-guided format makes navigation simple; you’ll access a map and GPS routes through the eATLAS app.
• The walking is light but steady, so wear comfortable shoes.
• The drinking age is 21, so be prepared to show ID if you plan to partake in the beverages.
• The last stop at Brando’s Speakeasy is open daily from 11 AM to 10 PM, giving you flexibility in timing.

This experience is ideal for adults who enjoy exploring urban sights alongside a drink or two, especially if they appreciate historic architecture, city views, and local legend. It’s perfect for those who want a laid-back, customizable outing with a dash of history, without the cost and formality of traditional guided tours. If you’re a fan of Chicago’s cocktail culture or want to merge sightseeing with a taste of local flavor, this tour offers a fun, budget-friendly way to do both.

For the price, the Chicago Cocktail Adventure Part 1 provides a delightful blend of scenery, history, and libation that’s perfect for a late afternoon or evening outing. The flexibility of the app-guided format lets you tailor the experience to your interests and schedule, making it a great choice for spontaneous planners or those who prefer a relaxed pace.

While the drinks are not included and menus may change, the stunning city views and walking route remain constant highlights. It’s best suited for adults interested in Chicago’s architecture, history, and cocktail scene who want to explore without the hassle and expense of a traditional tour.

Is this tour suitable for solo travelers?
Absolutely. The tour is self-guided and private, so it works well whether you’re traveling alone or with a small group.

Can I do this tour over multiple days?
Yes, the app format allows you to pause and restart, so you can spread the experience across several days if you prefer.

Are drinks included in the ticket price?
No, food and drinks are not included. You can purchase drinks at each stop, and the recommended drinks are just suggestions.

What should I wear?
Since the tour involves walking outdoors and visiting rooftop bars, wear comfortable shoes and dress appropriately for the weather.

What if menus change and signature drinks are unavailable?
You can order other drinks from the menu; the tour is designed to be flexible and enjoyable regardless of specific signature cocktail availability.

Is the tour accessible by public transportation?
Yes, the starting point near the LondonHouse is close to public transit options, making it easy to access without a car.

This Chicago cocktail tour offers a lighthearted yet insightful way to explore the city’s historic bars and architectural gems. Whether you’re a cocktail enthusiast, a history buff, or simply seeking a relaxing way to see downtown Chicago, it’s a memorable and affordable experience worth considering.