Chicago Skyline Sunday Funday Mimosa/Bloody Mary Party Cruise

Let’s be honest: there are plenty of ways to see Chicago from the water, but if you’re after something laid-back, a little festive, and with a splash of tropical fun, the Chicago Skyline Sunday Funday Mimosa/Bloody Mary Party Cruise might just catch your eye. We’ve looked into what this experience offers, and while it’s not a high-adrenaline adventure, it does promise a relaxed day of great views, drinks, and good vibes—perfect for those wanting a chill outing rather than an all-day tour.

What really caught our attention is the casual, tiki-bar theme that makes this cruise stand out from more traditional boat tours. Plus, the ability to purchase affordable drinks like $3 mimosas and $5 Bloody Marys onboard adds a fun, social element. Another perk is the flexible start times and the fact that it’s accessible—most travelers can hop aboard, and even dogs are welcome.

That said, it’s worth noting that this isn’t a lengthy or in-depth cruise, so if you’re looking for a comprehensive architectural tour or a full-day adventure, this might not check all those boxes. It’s more about relaxing, enjoying the scenery, and having a good time with friends or family. It’s best suited for folks who want a light, fun outing, especially if you’re celebrating a special day or just want to soak up Chicago’s skyline in a lively setting.

Key Points

• Casual, festive atmosphere with a tiki-themed boat adds character.
• Affordable drinks at the onboard cash bar make for a relaxed social vibe.
• Great views of Chicago’s skyscrapers and landmarks from the river and lake.
• Flexible start times provide convenience for planning your day.
• Shorter cruise duration (from 1 minute to 1.5 hours) suits those with tight schedules or looking for a quick experience.
• Limited bar service due to low passenger count might mean fewer options at times.

What to Expect from the Experience

The cruise kicks off at the Island Party Hut on Chicago Riverwalk, a lively starting point that’s easy to reach via public transportation or walking if you’re nearby. The meeting point sets a friendly, informal tone—and from there, you’ll board a tiki-themed vessel that’s designed to feel festive and relaxed.

The itinerary begins with a calm cruise along the Chicago River, where you can enjoy a beverage and listen to island tunes. This part of the journey is particularly scenic because you get close-up views of some of Chicago’s most iconic skyscrapers and the bascule bridges that add a picturesque touch to the city’s landscape. The vibe here is laid-back, perfect for snapping photos and soaking in the sights without the rush.

Once on Lake Michigan, the views open up even more. While the tour is relatively brief, it’s enough to give you a fresh perspective of the city’s skyline from the water—something you’ll want to capture. The boat’s tiki-bar theme makes for a lively, carefree environment, especially if you opt to buy a $3 mimosa or $5 Bloody Mary. The onboard cash bar offers these drinks, and it’s a nice touch to have a drink in hand as you watch the skyline change with the weather and time of day.

The Real Deal: Pros and Cons

One of the main advantages is the casual, friendly atmosphere. The reviews reflect this, with travelers noting the friendly staff and enjoyable vibe. For example, one guest mentioned that they had a “wonderful time” and appreciated the good drinks and perfect weather. The affordability of drinks like mimosas and Bloody Marys makes this an excellent option for a relaxed Sunday or a celebration, especially if you’re on a budget.

However, there are a few drawbacks to keep in mind. One review pointed out that only one bar was open because of low passenger numbers, which could limit drink options or result in waiting if you’re eager for a second round. The short ride outside the locks (about 30 minutes) was a bit of a surprise for some, especially those expecting a longer experience. Plus, since the cruise is relatively small (max 50 travelers), the service might feel more limited compared to larger boats with multiple bars and staff.

Price-wise, at $50 per person, it’s not a bad deal considering you’re getting scenic views and a fun atmosphere. The drinks aren’t included in the price, but the modest costs mean you can enjoy a drink or two without breaking the bank. It’s more about the experience and the setting than a full-on party—though it definitely has that festive, happy hour feel.

Breaking Down the Itinerary

Stop 1: Chicago River

The journey begins along the Chicago River, where you’ll find yourself close to some of the city’s most recognizable skyscrapers and the bascule bridges that open and close throughout the day. The views here are up-close and personal, giving you an intimate look at the architecture. It’s the kind of scenery that makes for great photos and offers a different perspective from the usual city stroll.

You can expect to listen to island-inspired tunes, which enhance the festive atmosphere. This part of the cruise is also the perfect chance to socialize, especially if you’re sharing a drink with friends or new acquaintances. Since the boat is air-conditioned and has a restroom onboard, it’s designed for comfort during the short trip.

Lake Michigan

As you move out onto Lake Michigan, the skyline opens up dramatically. The expansive views of Chicago’s buildings against the water are impressive, especially on a clear day. While the ride is brief—an advantage for those who prefer quick outings—it provides a refreshing change of scenery, with wind in your hair and panoramic views all around.

Drinks and Theme

The tiki bar theme adds a touch of tropical fun, and the fact that beverages like mimosas and Bloody Marys are available at a low cost makes it easy to relax and enjoy. Keep in mind, the bar service is limited, so if you’re hoping for a full bar experience, this might feel a bit restrained. Still, the casual vibe is what makes this cruise stand out.

Who Is This Tour Best For?

This experience is ideal for those looking for a casual, fun outing on the water. If you’re celebrating a birthday, catching up with friends, or just want a different way to see Chicago’s skyline without a massive tour or a lot of walking, you’ll likely enjoy it. The short duration and affordable drinks make it perfect for a laid-back afternoon, especially if you’re already planning to be on the Riverwalk or near downtown.

It’s not designed for those seeking in-depth architecture commentary or a longer, more comprehensive cruise. If you have kids or pets (dogs are welcome), this could be a nice, easy outing—just keep in mind the cruise’s limited duration and the fact that it’s more about relaxing than sightseeing.

Final Thoughts: Is It Worth It?

For about $50, you’re getting a lighthearted, scenic boat ride with a fun, tropical twist. It’s a good pick if you want to enjoy Chicago from the water without committing to a full-day tour. The affordable drinks and relaxed atmosphere make it a good choice for a weekend or special occasion.

If you’re after a more comprehensive experience or a longer cruise, you might look elsewhere. But for a quick, cheerful, and photo-worthy outing, this cruise hits the right notes. Remember, the experience’s success depends a lot on the weather and the crowd, so plan accordingly.

This tour offers a light, enjoyable way to see Chicago and unwind, especially when you want a break from the hustle, with the added bonus of a festive theme and good company.

FAQ

What is the starting point for this cruise?
It begins at the Island Party Hut located at 355 Chicago Riverwalk, which is easy to access via public transportation or walking nearby.

How long does the cruise last?
The duration can be from just 1 minute up to about 1 hour and 30 minutes, depending on the specific schedule you choose.

Are drinks included in the price?
No, drinks are not included. You can purchase mimosas for $3 and Bloody Marys for $5 at the onboard cash bar.

Is the tour suitable for children or pets?
Yes, most travelers can participate, and dogs are welcome, making it a family-friendly outing if you’re comfortable with pets on board.

What if the weather is bad?
Since the experience requires good weather, if canceled due to poor conditions, you’ll be offered a different date or a full refund.

How many people can fit on the boat?
The boat accommodates up to 50 travelers, which helps keep the experience intimate and lively.

Can I buy tickets last minute?
While most bookings are made about 8 days in advance, last-minute spots might be limited, so booking early is recommended to secure your preferred time.

In all, this Chicago Skyline Sunday Funday Cruise fits those wanting a light, fun, and scenic outing with a festive twist. It’s a low-key way to enjoy the city’s views, share some drinks, and maybe even celebrate a special day. If you’re okay with the shorter duration and limited bar service, it’s a laid-back, cheerful addition to your Chicago itinerary.