Chicago Cocktail Adventure Part 1

If you’re looking for a way to combine Chicago’s vibrant bar scene with a touch of local history and architecture, the Chicago Cocktail Adventure Part 1 offers a unique, flexible experience. This tour is perfect for those who enjoy a good drink, want to learn a little about the city’s cocktail past, and prefer exploring at their own pace. While it’s priced very affordably at just $5 per person, the real value lies in its casual, customizable format and the gorgeous views along the way.

What we love about this tour is how it balances history, stunning city vistas, and a chance to try some of the city’s best cocktails—without feeling rushed or overly structured. Plus, the use of an app means you can start, pause, or revisit the stops whenever it suits your schedule. One potential drawback might be that the specific drinks recommended aren’t always available at every stop, but that’s part of the casual charm. This experience suits travelers who enjoy a laid-back, adult-oriented outing and are curious about Chicago’s cocktail heritage, especially those comfortable with self-guided tours.

Key Points

• Affordable Price: At just $5, this tour offers excellent value, especially considering the included app-guided experience.
• Flexible & Self-Paced: Use the app to start, stop, or spread out your stops over multiple days—perfect for busy or indecisive travelers.
• Great Views & Architecture: Walk along Millennium Park, taking in iconic sights like the Crown Fountain and Harold Washington Library.
• Historic Stops & Modern Spots: From rooftop bars with city panoramas to historic buildings like the Monadnock, the tour offers a mix of old and new.
• Drink Recommendations: While some specific cocktails may no longer be available, you’re free to order whatever appeals at each stop.
• Limited Food & Drink Included: This is a tasting tour, so drinks and snacks are on you, but the focus is on atmosphere and stories.

A Detailed Look at the Chicago Cocktail Adventure

Starting Point: LondonHouse Chicago

Our journey begins at the LondonHouse Chicago, a stylish hotel located at 85 E Wacker Dr. Its rooftop bar is where many might choose to start, thanks to the stunning city skyline views you’ll get from above. The setting is perfect for a slow sip as you get acquainted with the tour’s vibe—urban elegance with a side of Chicago’s architectural grandeur. Since admission is free, we think this is an excellent value and a prime spot for a photo or two before heading out.

This first stop sets the tone for the tour—relaxed, scenic, and steeped in Chicago’s modern glamour. The app-guided map and GPS will help you navigate to the subsequent stops, making the experience seamless even if you’re not familiar with the city.

Walking Along Millennium Park

From LondonHouse, you’ll take a leisurely stroll past Millennium Park, one of Chicago’s most iconic outdoor spaces. The Crown Fountain makes a lovely photo backdrop, and the walk allows you to soak in the city’s architecture and energy. This pedestrian-friendly route is a highlight—combining urban scenery with a sense of connection to the city’s cultural heart.

The Monadnock Building & Harold Washington Library

As you meander through the Loop, you’ll pass by the Monadnock Building, a historic structure famed for its early 20th-century design—a real treat for architecture enthusiasts. Nearby, the Harold Washington Library impresses with its modern architecture, offering a striking contrast and a chance to appreciate Chicago’s architectural diversity. While these aren’t stops with drinks, they add context and visual interest, enriching your understanding of the city.

Final Stop: Brando’s Speakeasy

Your tour concludes at Brando’s Speakeasy, located on South Dearborn Street. This spot embodies Chicago’s clandestine bar history, offering a cozy yet lively atmosphere. It’s the perfect place to reflect on your adventure, sip a cocktail, and consider the stories you’ve gathered along the way.

What to Expect at Each Stop

While the tour recommends a specific cocktail at each location, drink choices are entirely up to you. A quoted review notes that some venues might not have the signature drinks listed, but the flexibility to order from the menu means you can enjoy what’s available. The price of drinks and food is not included, so budget accordingly—expect to purchase your own beverages, which is a fair trade for the curated experience.

The First Stop: Rooftop View

The rooftop bar at LondonHouse not only offers spectacular views but also sets a high standard for ambiance. Expect a relaxed atmosphere with cityscape panoramas—ideal for Instagram shots or just soaking in the skyline. The 30-minute stop here is enough to enjoy a drink, take photos, and get a sense of Chicago’s modern face.

The Walking Segment

Walking between stops allows you to appreciate Chicago’s architecture and street life—a quiet, contemplative way to enjoy the city’s heartbeat. The app’s map and GPS help you stay on track, offering turn-by-turn directions that make the self-guided nature accessible even to first-time visitors.

Historic & Architectural Highlights

Passing by buildings like the Monadnock and the Harold Washington Library, you’ll gain a visual history of the city’s architecture, adding depth to your experience beyond just the cocktails. One reviewer mentioned the architecture as a highlight, noting how walking by these structures enhances the tour’s cultural dimension.

Final Stop at Brando’s

At Brando’s Speakeasy, you’ll find a cozy, welcoming vibe, reminiscent of Chicago’s Prohibition-era bars. If you’re interested in the city’s secret bar past or just want a strong cocktail to cap off your evening, this spot delivers.

Authentic Feedback from Participants

A review from a recent participant highlights some real-world nuances: “None of the three places we went to had the signature drinks recommended by Viator,” but also notes that they enjoyed ordering from the menu anyway. The flexibility to choose your drinks is appreciated, especially given that menu offerings can change.

Another observer points out that the views from the rooftops and walking along Millennium Park are standout features—an aspect that elevates the experience from just a bar crawl to a mini city tour with a drink in hand.

Analyzing Value and Practicalities

For just $5, this tour offers access via the app and the chance to explore some of Chicago’s most scenic and architecturally significant areas. The self-guided format allows you to pace yourself, making it ideal for travelers who prefer a bit of independence. Since the drinks aren’t included, you can control your budget while enjoying the freedom to explore different venues.

Timing-wise, the tour is approximately three hours, but with the app, you could stay longer or shorter depending on your interest. The flexible approach makes it suitable for a late afternoon or early evening activity, perfect for winding down or kicking off an evening out.

Practical Tips for Participants

• Bring ID, as the legal drinking age in Illinois is 21.
• Consider spreading the stops over several days if you prefer a more relaxed pace.
• Use the app’s GPS for easy navigation between stops—no need to worry about missing a highlight.
• Be prepared to purchase your own drinks and snacks—this isn’t included in the ticket price.
• Wear comfortable walking shoes; the city sidewalks are your pathway.

Who Will Love This Tour?

This experience suits adults who enjoy urban exploration combined with a few drinks and are comfortable navigating at their own pace. It’s especially good for those with an interest in architecture, city views, or Chicago’s cocktail history. Travelers seeking a low-cost, flexible outing that’s more about enjoying the city’s vibe than a structured tour will find this perfect. If you’re after a highly curated, all-inclusive experience, you might want to look elsewhere, but if you enjoy discovery and independence, this is quite the find.

The Sum Up: Is It Worth It?

The Chicago Cocktail Adventure Part 1 offers a low-cost, self-guided way to combine a city walk with a tasting experience. Its greatest appeal is the stunning views, walkable route, and flexibility—allowing you to make it your own. While the drink recommendations might occasionally fall short or change, the overall experience delivers a fun, laid-back way to discover Chicago’s cocktail scene and architecture.

If you’re a traveler who values authentic, unpretentious experiences and prefers exploring at your pace, this tour provides a great way to soak in the city’s sights while enjoying a cocktail or two. It’s a budget-friendly, adult-oriented outing that can be tailored to your schedule and interests.

FAQ

Is this tour suitable for solo travelers?
Absolutely. The tour is self-guided via the app, so you can explore alone or with a group. It’s designed to give you independence while still providing guidance on the route.

Are drinks included in the price?
No, beverages and food are not included. You will need to purchase your own drinks at each stop, but the price of the tour itself is just $5.

What if I don’t like the recommended drinks?
That’s perfectly fine. The tour recommends specific cocktails, but you’re free to order whatever you prefer from the menu.

Can I take this tour over multiple days?
Yes. The app allows you to start, stop, and restart the tour at your convenience, making it easy to spread out over several days if you prefer.

Is there any age restriction?
Yes, participants must be 21 or older to enjoy alcoholic beverages. Be prepared to show ID.

How long does the tour take?
Approximately 3 hours, but you can adjust the pace depending on how long you want to linger at each spot.

What’s the best time of day to do this?
Late afternoon or early evening works well, especially if you want to enjoy the city lights and sunset views from rooftops.

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

What’s the cancellation policy?
You can cancel up to 24 hours in advance for a full refund. Less notice means no refund, so plan accordingly.

This tour is a fantastic, wallet-friendly way to see Chicago’s skyline, indulge in a cocktail or two, and learn a bit about the city’s past—all at your own pace. Whether you’re a seasoned local or a first-time visitor, it offers a relaxed, authentic spin on city exploring.