Monday Night Concert Series

Experience the Monday Night Concert Series in Chicago

If you’re looking for an evening that combines the charm of a sailing cruise with the soulful sounds of live music, the Monday Night Concert Series aboard Tall Ship Windy is worth considering. For around $80, you get approximately two hours of entertainment, set against the stunning backdrop of Chicago’s skyline. The concert features talented musician Michael Charles, known for his engaging performances and guitar mastery.

What we love about this experience is the freedom to move around the ship while the music plays—imagine dancing on the deck with the city lights twinkling behind you. Plus, the casual, intimate atmosphere makes it an ideal way to unwind early in the week. Still, keep in mind that these tickets tend to sell out fast, so booking early is essential. It’s best suited for those who enjoy live music with a relaxed, scenic setting and don’t mind a bit of boat motion.

A minor consideration is the non-refundable nature of the ticket, which means you should be certain about your plans before booking. But if you’re a music lover or someone curious about experiencing Chicago from a different perspective, this cruise offers a charming blend of entertainment and sightseeing—perfect for couples, solo travelers, or small groups seeking an authentic local experience.

Key Points

• Affordable evening activity combining music and scenic views.
• Freedom to explore the ship during the performance.
• Early booking recommended due to high demand.
• Perfect for music fans wanting a relaxed, memorable night.
• Accessible via public transportation and accommodating service animals.
• Non-refundable tickets require confirmation of plans beforehand.

A Deep Dive into the Monday Night Concert Series

What is the experience like?

This cruise offers an approximate two-hour journey on Tall Ship Windy, starting at 7:00 pm from 600 E Grand Ave, Chicago. The main draw is the live performance by Michael Charles, a musician who has garnered praise for his guitar skills and engaging stage presence. While the music plays, you’re free to move about the ship, taking in the vistas or relaxing on the deck as the wind and waves add to the ambiance.

The setting of Chicago’s skyline at night is just as stunning from the water as it is from land—maybe even more so when paired with jazz, blues, or folk tunes filling the air. The ship itself is a classic tall ship, adding a touch of nautical charm that elevates the experience beyond just another concert.

How is the itinerary structured?

The cruise begins promptly at 7:00 pm, with the performance taking center stage. Since the activity ends back at the starting point, there’s no need for complicated transfers or additional planning. The meeting point is conveniently located near public transportation, making it easy to reach without hassle.

While there are no specific stops along the way, the main attraction is the live music and the opportunity to move freely around the ship. This flexibility allows you to choose whether to stay close to the band, enjoy a drink on deck, or simply take in the Chicago skyline as the music provides a perfect soundtrack.

What makes this experience special?

The combination of live music and a scenic cruise is what we love about this tour. We loved the way the music fills the space—it’s intimate but lively. Plus, the fact that you can wander around the ship means you’re not confined to a seat or a specific spot, allowing for a more relaxed night.

The music itself, performed by Michael Charles, is often described as soulful and engaging. One reviewer noted, “great music, with Michael Charles,” which indicates the quality of the performance. Since the tour is capped at 99 travelers, it avoids the overcrowded feeling common in larger events, maintaining a cozy vibe.

Who should consider this tour?

This cruise is ideal for music lovers who enjoy a laid-back environment and scenic views. It’s also suitable for those who appreciate a unique night out in Chicago that combines entertainment with sightseeing. Small groups, couples, or solo travelers will find this experience particularly charming.

Pricing and value

At $80.72 per person, this experience offers good value for an evening of live music combined with a boat ride. Compared to land-based concerts or dinner cruises, this is a reasonably priced option that provides more flexibility and less formality. The ability to move freely around the ship enhances the value, making it more than just a typical concert.

Practical considerations

Since the tickets are non-refundable, plan your evening carefully. The cruise is scheduled in the early evening, so it fits well into a broader itinerary without taking up your entire day. Accessibility is addressed through proximity to public transportation and allowance for service animals.

Summing it Up: Is it Worth It?

For travelers who crave a relaxing yet lively experience on the water, this cruise offers a charming way to spend an evening in Chicago. The live music by Michael Charles is a highlight, providing authentic entertainment in a scenic setting. The ability to move around the ship gives it an informal, intimate feel that can’t be matched by traditional concert halls.

While the price might seem high for just two hours, keep in mind that you’re paying not only for the performance but also for the unique ambiance of being on a tall ship with Chicago’s skyline as your backdrop. It’s especially suited for those looking for a different way to enjoy the city’s vibrant culture without the crowds.

This tour is best suited for music fans, couples, or solo explorers who appreciate the combination of live performance and scenic views, and who don’t mind booking ahead and paying a bit extra for a memorable, authentic experience.

Frequently Asked Questions

Is the ticket non-refundable?
Yes, the tickets are non-refundable and cannot be changed once booked. Be sure about your plans before purchasing.

What time does the cruise start?
The cruise begins promptly at 7:00 pm, with boarding likely happening shortly beforehand.

Where do I meet the tour?
You meet at 600 E Grand Ave, Chicago, which is near public transportation for easy access.

Can I move around during the performance?
Absolutely. One of the highlights is that you’re free to move about the ship while the music plays.

Is the activity suitable for everyone?
Most travelers can participate, and service animals are allowed. It’s a relaxed environment suitable for a wide range of guests.

How long is the cruise?
The whole experience lasts about two hours.

What is included in the price?
You get live music, scenic views, and the opportunity to explore the ship freely, all for around $80.72 per person.

Are there any other similar experiences?
Yes, if you enjoy river cruises or architecture tours, there are several options in Chicago, but this one combines music and scenery uniquely. Check similar experiences here for more ideas.

Whether you’re a dedicated music enthusiast or just looking for a relaxed way to experience Chicago at night, the Monday Night Concert Series aboard Tall Ship Windy offers good value and genuine charm. It’s a chance to enjoy live music, stunning views, and perhaps a new perspective on the city’s waterside scenery—all bundled into a memorable two-hour outing.