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Experience an evening of live music on a scenic Chicago river cruise, with flexible movement and authentic performances, perfect for those seeking local flavor.
Introduction
Looking for a different kind of night out in Chicago? The Monday Night Concert Series aboard the Tall Ship Windy offers an inviting blend of live music and sightseeing from the city’s scenic waterways. Though there are no reviews yet, the concept feels promising—an evening spent enjoying live tunes while drifting past Chicago’s iconic skyline, all for a reasonable price of around $80.
What we really appreciate about this experience is the flexibility to move around the ship while music plays—a bonus for those who love mingling or simply want to find the perfect vantage point. It also takes place in the early evening hours, starting at 7:00 pm, which makes it a great way to wind down after a day of sightseeing or dining. One potential consideration: the experience is non-refundable, so it’s best to book only if you’re confident about the weather and your plans. This tour suits travelers who want a relaxed, authentic Chicago evening with a musical twist, especially music lovers and those curious about the local scene.


When considering the Monday Night Concert Series, the first thing that catches your attention is the setting. Starting at 600 E Grand Ave in Chicago, the cruise boardings are conveniently located, making it accessible whether you’re staying downtown or nearby. The Tall Ship Windy, well-known for its sailing adventures, now extends its charm to this musical evening, offering a more relaxed and social environment compared to more formal concert venues.
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The entire evening is about combining music with the scenic backdrop of Chicago’s waterways. The cruise kicks off promptly at 7:00 pm, giving you plenty of time to settle onboard, grab a drink, and find a comfortable spot. Although the specific stops are not detailed beyond the start and end at the same point, what makes this cruise special is the ability to move around freely on the ship. You can listen to Michael Charles perform, all while wandering to different parts of the vessel or standing at the rail to snap photos of the city skyline.
Michael Charles, a talented musician, leads the performance. While reviews are not available yet, the description suggests a great night of music, likely featuring a mix of acoustic, blues, or folk tunes—genres that complement the relaxed, maritime setting. The music plays throughout the cruise, and you’re encouraged to enjoy it at your own pace, making the experience more personal.
The Tall Ship Windy is a sturdy, classic vessel, well-suited for hosting events like this. With ample space and the option to move freely, you’ll find that this is less about a formal concert and more about enjoying live music in a convivial, open-air environment. Expect to be on deck, with stunning views of Chicago’s skyline, especially as the city lights begin to twinkle at night.
At $80.72 per person, this cruise offers a distinctive value for those seeking an authentic, relaxed Chicago experience. Compared to tickets for traditional concerts or private boat rentals, this outing combines live music, scenic views, and a unique setting for a comparable price. Keep in mind, the ticket is non-refundable, so it’s wise to confirm your plans beforehand.
The tour’s duration of about 2 hours strikes a nice balance—long enough to enjoy the music and scenery without feeling fatigued. Since the activity is capped at 99 travelers, it promises a more intimate environment compared to larger crowd-based events. The proximity to public transportation makes it accessible, and service animals are permitted, which is considerate for travelers with disabilities or emotional support animals.
If you’re craving an evening that combines music and sightseeing without the hustle of large crowds, this cruise could be a good fit. It’s particularly appealing if you enjoy live performances in relaxed settings or want to see Chicago from a different perspective. Music enthusiasts will appreciate the chance to hear Michael Charles in an intimate, scenic setting, while those seeking a romantic or social outing will find the atmosphere inviting. It’s also a great option for travelers who value authentic local experiences over touristy attractions.

While the ticket price might seem modest, it’s important to assess the value in terms of the experience itself. The ability to move freely about the vessel adds a layer of comfort and personalization that many concert venues lack. Plus, the combination of live music and scenic views offers a memorable way to spend an evening in Chicago, especially if you appreciate genuine, unpretentious entertainment.
However, it’s worth remembering that this is a non-refundable activity, so weather or last-minute changes could impact your plans. If you’re flexible and prepared for possible adjustments, you’ll find that this cruise offers a charming and laid-back way to enjoy Chicago’s waterscape.

This experience is ideal for music lovers who enjoy a relaxed, social environment. It suits adventurous spirits eager to combine sightseeing with entertainment, as well as locals and visitors who want a taste of Chicago’s maritime charm. It’s especially appealing to those who appreciate authentic, local performances and are comfortable with the idea of a casual, open-air concert. If you’re traveling with family, friends, or even solo, the informal vibe makes it easy to connect and enjoy.

Is the tour suitable for all travelers?
Yes, most travelers can participate, and service animals are allowed, making it accessible for many.
What is the meeting point for the cruise?
The cruise starts at 600 E Grand Ave, Chicago, IL 60611, and you’ll meet there before boarding.
How long does the cruise last?
The experience lasts approximately 2 hours, providing a comfortable window to enjoy the music and views.
Can I move around the ship during the concert?
Absolutely. You’re free to move about the ship while the music plays, which adds to the relaxed atmosphere.
What is included in the price?
The ticket grants you entry to the concert on the Tall Ship Windy, along with scenic views of Chicago from the water.
Is the ticket price refundable?
No, this activity is non-refundable and cannot be changed once booked, so plan accordingly.
How do I get there using public transportation?
The meeting point is near public transit options, making it easy to reach without a car.
To sum it up, the Monday Night Concert Series offers a delightful blend of live music, scenic waterway views, and a laid-back atmosphere. It’s perfect for those seeking an authentic Chicago experience that’s a bit different from the usual tourist fare. Whether you’re a music enthusiast, a couple looking for a romantic evening, or a solo traveler craving a relaxed social outing, this cruise provides a memorable way to enjoy the city’s waterfront. Just remember to book early, dress comfortably, and be prepared for a non-refundable adventure that promises genuine local flavor.