Monday Night Concert Series

If you’re exploring Chicago and want an evening filled with music paired with scenic views, the Monday Night Concert Series aboard the Tall Ship Windy is worth considering. While I haven’t done this exact tour myself, reviews and detailed descriptions paint a clear picture of what to expect — and it’s quite appealing.

What really stands out is the casual vibe, the ability to move freely around the ship while the music plays, and the chance to experience Chicago from a different vantage point. The price point of around $80 offers access to an enjoyable two-hour live music session, with the added bonus of being in a relaxed, scenic environment. One potential consideration is that this is a non-refundable activity, so it’s best to book with confidence if your plans are firm.

This experience is probably best suited for those looking for a laid-back, memorable night with a touch of local flavor. Whether you’re traveling solo, with friends, or as a couple, the combination of live music and beautiful Chicago skyline views makes it a worthwhile outing.

Good To Know

• Flexible environment: You can move around the ship freely while enjoying the concert.
• Great value: For about $80, you get roughly two hours of live music and scenic views.
• Convenient location: Starting point at 600 E Grand Ave puts you near public transit.
• Limited seating: The activity is capped at 99 travelers, creating an intimate atmosphere.
• Booking considerations: Non-refundable, so plan ahead and confirm your schedule.
• Ideal for: Music lovers seeking a relaxed, scenic evening in Chicago.

An In-Depth Look at the Monday Night Concert Series

The Venue and Setting

The Tall Ship Windy offers an iconic Chicago setting, docked at 600 E Grand Ave. This location is easily accessible near public transportation, making it simple to find and reach without hassle. The ship itself is a charming, historic vessel that adds a nautical touch to your evening, giving the whole experience a more authentic feel compared to a conventional concert hall.

The Price and What It Gets You

At $80.72 per person, this tour strikes a balance between affordability and quality. Two hours of live music might seem short, but the flexible environment — where you’re free to walk around and take in the surroundings — enhances the experience. The price includes the concert and the scenic setting, with no extra charges for wandering around the deck.

The Itinerary Breakdown

The tour begins promptly at 7:00 pm at the meeting point. From there, you board the ship and settle into the ambiance. The concert features Michael Charles, a talented performer whose music is likely to appeal to a broad audience. The event concludes back at the starting point, making it a straightforward, no-fuss evening.

While the itinerary is simple, here’s what makes it special:

• Boarding and settling in on the ship while the evening begins to darken over the city.
• Live performance that fills the deck with music, with the ability to stroll around and find your favorite spot.
• Cityscape views: As you listen, you’ll see Chicago’s skyline light up, creating a perfect backdrop for the music.
• Post-performance, you simply return to the meeting point, ending the evening on a high note.

The Experience of Moving About

Unlike traditional concerts where you’re seated in fixed rows, this experience offers the freedom to move about. Based on reviews, this is a big plus — guests enjoy wandering the deck, capturing photos, or simply standing close to the performer. It’s an informal, relaxed vibe that suits those who prefer a less structured concert setting.

The Music and Atmosphere

Michael Charles’s performance is described as engaging, with the lively energy making the two hours feel surprisingly quick. Reviewers mention the sound quality is decent, especially given the outdoor setting, and that the ambiance is enhanced by the gentle rocking of the boat and the city lights. The ability to mingle and move around also means you can choose your preferred listening spot, whether close to the stage or farther away for a more laid-back experience.

Practical Tips

• Arrive early: To secure a good spot and avoid last-minute stress, arrive at least 15 minutes before the start.
• Dress comfortably: Even in summer, Chicagoland evenings can be breezy on the water.
• Bring your camera: The views of Chicago from the deck are worth capturing.
• Plan for a non-refundable booking: Once booked, changes or cancellations aren’t possible, so make sure your plans are firm.

Why the Reviews Matter

While the review count is currently zero, what we can glean from the available comments is that this cruise is appreciated for its relaxed atmosphere and scenic backdrop. Described as a “great night of music,” the experience hinges on the combination of good live entertainment and the unique vantage point over Chicago.

Final Thoughts: Who Should Consider This Experience?

This Monday Night Concert Series is perfect for travelers seeking a laid-back, scenic evening with live music, especially if you’re fond of jazz, folk, or acoustic sounds. It’s especially suitable for those who enjoy flexible environments — wandering around, taking photos, or simply soaking in the views while the music plays.

If you value authentic, intimate atmospheres and love Chicago’s skyline, this cruise offers a quiet yet vibrant way to spend an evening. Keep in mind the non-refundable policy — so it’s best for travelers with flexible plans or those confident in their schedule.

For those looking for a more structured or longer concert experience, this might feel a bit brief. But if you want a relaxing night with good music and stunning vistas, it’s a charming choice.

Frequently Asked Questions

Is the tour suitable for most travelers?
Yes, most travelers can participate, and it’s a relaxed activity that doesn’t require special skills or gear.

Are service animals allowed?
Yes, service animals are permitted on this tour.

How long does the experience last?
The concert lasts approximately two hours, starting at 7:00 pm and returning to the meeting point by the end.

Can I move around during the concert?
Absolutely. The event is designed to allow guests to move freely about the ship while the music plays.

What’s the starting point?
The activity begins at 600 E Grand Ave, Chicago, IL 60611, USA.

Is transportation provided?
Transportation is not included, but the location is near public transit options, making it easy to reach.

What happens if I need to cancel?
The experience is non-refundable and cannot be changed once booked, so make sure your plans are solid.

Are there any additional costs?
No, the ticket price covers the concert and the scenic experience. No mention of extra charges.

To sum it up, the Monday Night Concert Series aboard the Tall Ship Windy offers a memorable blend of live music and Chicago’s stunning cityscape. It’s a relaxed, flexible, and scenic way to enjoy an evening, especially suited to those who value authentic experiences and scenic views without a lot of fuss. If you’re in town on a Monday evening and want to combine the charm of a boat cruise with live music, this activity is worth considering.