Monday Night Concert Series

Imagine strolling onto a historic ship in the heart of Chicago, with the city skyline as your backdrop, and settling in for an evening of live music that feels both intimate and expansive. That’s essentially what the Monday Night Concert Series offers — a chance to experience Chicago from a different perspective, combining the romance of a ship at sunset with the soulful sounds of Michael Charles. Whether you’re a music lover or just seeking a unique night out, this cruise offers a blend of scenic beauty, relaxed atmosphere, and a touch of maritime charm.

What we love about this experience is that it allows you to move freely around the ship while the music plays, giving you the flexibility to socialize, find a quiet spot, or snap some memorable photos. The value for the price — roughly $80 per person — is appealing if you’re after a cultural evening that’s more than just typical dinner or bar night. One possible drawback? It’s a non-refundable booking, so you’ll want to be sure your plans are firm before reserving. This experience suits those who enjoy live music, scenic views, and informal, relaxed outings in Chicago.

Key Points

• Flexible Movement: You’re free to wander around the ship during the concert, enhancing your comfort and enjoyment.
• Scenic Location: The Tall Ship Windy offers a striking setting on Lake Michigan, with Chicago’s skyline providing a perfect backdrop.
• Duration and Price: About 2 hours for approximately $80, making it a reasonable investment for a special night out.
• Early Booking Recommended: The tour tends to sell out, so booking in advance is wise.
• Accessible: Near public transportation and accommodating service animals, this is suitable for most travelers.
• Limited Reviews: As of now, there are no reviews, but the experience seems to align with typical river or scenic cruises in the city.

What the Tour Offers

The Monday Night Concert Series is designed as a relaxing, scenic cruise with a musical twist. Starting at 600 E Grand Ave, the tour kicks off at 7:00 pm, just as Chicago’s evening lights are beginning to twinkle. Hosted by Tall Ship Windy, a vessel renowned for offering lake cruises and special events, the cruise lasts around two hours — giving you enough time to soak in the views and enjoy the music without feeling rushed.

The cost of $80.72 per person covers the live performance by Michael Charles, a talented musician whose tunes likely span genres that appeal to various tastes. While the exact style isn’t specified, live music on a ship creates an intimate, informal atmosphere that’s perfect for unwinding. An added benefit is the freedom to move about the ship; unlike traditional seated concerts, you can explore, chat, or find a cozy corner as the music plays.

The Itinerary in Detail

The journey primarily focuses on enjoying the music and scenery rather than multiple stops. The cruise begins at the designated meeting point, where you board the Tall Ship Windy. As the vessel sets sail, you’re treated to panoramic views of Lake Michigan and Chicago’s iconic skyline. The boat’s design and open deck layout encourage a feeling of casual freedom, so you might find yourself leaning against the rails, camera in hand, or simply soaking in the sunset.

Since the cruise is approximately two hours, it allows enough time to relax and mingle. There are no specified stops along the way, but the experience emphasizes spectacle and ambiance. The music performance is likely held on deck, with ample space for everyone to enjoy without feeling cramped.

What Travelers Might Expect

Although reviews are not yet available, based on the description, you can expect a laid-back atmosphere with the ability to roam freely. The near public transportation access makes it convenient to reach the starting point, and service animals are allowed, making this inclusive for those with support animals. Since most travelers can participate, it’s a good fit for couples, small groups, or solo travelers seeking a non-traditional night out.

The non-refundable policy is worth noting — it underscores the importance of confirming your plans beforehand. Weather could influence the experience, so it’s wise to check the forecast and dress appropriately for an outdoor or semi-outdoor setting.

The Value Proposition

At roughly $80 for two hours, this cruise offers an experience that balances scenic beauty, live music, and relaxed transportation. Compared to other Chicago attractions, it’s fairly priced considering the unique setting and entertainment. For music fans, or those seeking a different way to spend an evening, it provides a memorable option that combines the maritime charm of Chicago’s lakefront with the city’s vibrant music scene.

This experience suits music lovers looking for a relaxed, intimate setting. It’s perfect for couples wanting a romantic evening with scenic views, or small groups celebrating a special occasion. The flexibility to move about makes it appealing to those who dislike being confined to a seat. If you’re interested in Chicago’s lakefront, live performances, or sailing with a city backdrop, you’ll likely find this cruise rewarding.

However, it’s not ideal for travelers seeking a structured, narrated tour or a full-day activity. Since it’s non-refundable and dependent on good weather, those with flexible plans or in need of a guaranteed indoor event might prefer other options.

• Book early to secure your spot, especially during peak seasons or weekends.
• Arrive at the meeting point on time — the cruise departs sharply at 7:00 pm.
• Dress in layers; evenings on the lake can cool down unexpectedly.
• Consider bringing a camera for sunset shots or cityscape photos.
• Remember, this is a non-refundable booking, so confirm your plans beforehand.
• Since most travelers can participate, it’s accessible, but check for any specific needs or questions with the provider.

What is the cost of the tour?
The price is approximately $80.72 per person, covering the live music and scenic cruise.

How long does the cruise last?
It lasts about two hours, giving plenty of time to relax and enjoy both the music and views.

Where does the tour start?
It begins at 600 E Grand Ave, Chicago, at 7:00 pm.

Can I move around during the concert?
Yes, you are free to move about the ship during the performance, which adds to the casual and comfortable vibe.

Is the tour suitable for all travelers?
Most travelers can participate, and service animals are allowed. Check specific needs with the provider if necessary.

Is this tour suitable for weather changes?
Since weather can impact outdoor activities, it’s advisable to check forecasts and dress accordingly. The experience is primarily outdoors or semi-outdoors, depending on weather.

What is the cancellation policy?
This experience is non-refundable and cannot be changed once booked.

Are there any other similar experiences?
Yes, there are other Chicago river and architecture cruises, but this one emphasizes live music and a more casual, free-movement environment.

How many people will be on the cruise?
The tour is limited to a maximum of 99 travelers, ensuring a comfortable and social atmosphere.

What kind of music is played?
While not specified, you can expect live performances by Michael Charles, likely offering an engaging musical experience.

For those seeking a scenic evening with a musical backdrop, the Monday Night Concert Series on Tall Ship Windy offers a distinctive way to enjoy Chicago’s lakefront. Its relaxed environment, combined with the freedom to explore and the stunning skyline views, makes it a memorable experience for a variety of travelers. While the non-refundable policy requires some planning, the opportunity to enjoy live music aboard a historic vessel is well worth it.

This cruise is particularly well-suited for music aficionados, couples, and small groups looking for a laid-back, scenic night out that blends natural beauty with cultural entertainment. If you’re after a flexible, fun, and atmospheric experience in Chicago, this cruise deserves a spot on your list.

Remember: Secure your tickets early, dress for the weather, and prepare for an evening that combines the best of Chicago’s music scene with the charm of lake sailing.