Chicago Air & Water Show

If you’re considering catching Chicago’s famous Air & Water Show, you might want to skip the crowded streets and instead opt for a vantage point on the water. This Chicago Air & Water Show tour aboard the Tall Ship Windy offers a unique perspective, combining the thrill of aerial demonstrations with the serenity of Lake Michigan. With its prime positioning, responsive crew, and flexible sailings, this experience promises to be one of the most memorable ways to witness the city’s iconic event.

Among the many things we love about this tour are the spectacular lake vistas, the personalized positioning by the crew, and the opportunity to see the show from a quiet, spacious vessel rather than a packed shoreline. A minor consideration is that this tour runs non-refundable and can be affected by show delays, so planning ahead is key. Ideal for families, aviation enthusiasts, or groups seeking a relaxed yet exciting way to enjoy the spectacle, this tour offers a blend of comfort and awe-inspiring views.

Good To Know

• Prime Viewing Locations: The boat is positioned near show center for optimal viewing.
• Flexible Schedules: Two sailings — one before and one during the main event — maximize chances to see different parts of the show.
• Expert Crew: The team, including Captain Bruce, is praised for their courteous, helpful attitude.
• Stunning Lake Views: Enjoy Chicago’s skyline from the water, creating a perfect backdrop for photos.
• Inclusive Experience: Admission to the Air & Water Show is included, with the boat maneuvered to ensure the best possible vantage point.
• Limited Refund Policy: This tour is non-refundable, so plan accordingly.

An In-Depth Look at the Chicago Air & Water Show Tour

An Introduction to the Experience

This tour, offered by Tall Ship Windy, stands out as a fantastic way to view Chicago’s Air & Water Show without battling crowds on land. Instead, you’ll settle into the comfort of a large, historic sailing vessel that can be carefully positioned to give you the clearest, safest view of the aerial performances. The timing is carefully coordinated: a 10 am sail kicks things off with a scenic cruise, giving early birds a peaceful lake experience, while the 1 pm sail is designed to coincide with the main event, including the impressive Thunderbirds demonstration.

What makes this experience particularly appealing is the flexibility of the schedule. You have two opportunities to see the show from the water, and the Captain’s skill in maneuvering the ship guarantees a good vantage point, even if the show is delayed or runs over. The entire experience lasts about two and a half hours, which strikes a perfect balance — long enough to soak in the views but not so long as to become tiring.

The Itinerary and What to Expect

The day begins at the Original Rainbow Cone, a fun and recognizable meeting point in Chicago. From there, you’ll board the Tall Ship Windy, a historic vessel with plenty of space for passengers to relax and take in the scenery. The first sail at 10 am offers a peaceful cruise on Lake Michigan, with the captain positioning the ship in the best location to view the air and water demonstrations.

The main highlight arrives during the second sail at 1 pm, when the ship is positioned near show center — a spot carefully selected by the crew for optimal viewing of the aerial displays, including jets, stunt planes, and the famous Thunderbirds. Reviewers mention that the crew is attentive and friendly, making sure everyone gets a good view. One reviewer highlighted how the crew “maneuvered the ship so everyone could view the planes overhead,” demonstrating their commitment to passenger experience.

The aircraft and water demonstrations are the core of this experience. While you won’t get up close, the vantage point from the water offers a sweeping perspective of the show — a different experience from the crowded shoreline, with the added benefit of relaxing on a spacious boat.

Views and Photo Opportunities

One of the biggest draws of this tour is the stunning backdrop of Chicago’s skyline. From the water, you’ll see iconic structures like the Willis Tower and John Hancock Center framing the sky, creating a perfect setting for photos. As one reviewer noted, “you’ll love the views of Chicago from the lake,” which are especially impressive when the aircraft streak overhead.

Crew and Service Quality

The crew’s helpfulness is frequently praised, with comments about their courteous and kind attitude. Notably, they encouraged photos with the Captain and involved children in activities like hoisting sails, enhancing the family-friendly vibe. The captain, Bruce, and his team are lauded for their professionalism, ensuring safety and comfort throughout the trip.

Price and Value

At $154 per person, this tour offers a memorable viewing experience that combines the thrill of the show with the comfort of a boat cruise. Considering that the ticket includes admission to the show itself and a prime viewing location, the price represents good value for those wanting a more relaxed, exclusive perspective. Plus, compared to the crowded streets or paid viewing areas, this water-based vantage point offers a more comfortable and less hectic experience.

Practicalities and Tips

• Booking in advance is recommended; most travelers book about 10 days ahead, especially during peak season.
• The tour is suitable for travelers with moderate physical fitness — the boat is accessible, but some walking or standing may be involved.
• Service animals are allowed, which is helpful for travelers with disabilities or emotional support animals.
• Be aware that the tour is non-refundable, so plan your schedule accordingly.
• The experience ends back at the original meeting point, making transportation easy to arrange.

Authentic Experiences from Reviews

Real travelers appreciated the personalized experience. One reviewer called it “the perfect way to view The Thunderbirds,” praising the helpful crew and noting how they made the experience fun for children, such as hoisting sails together. Another mentioned how the crew maneuvered the ship to ensure everyone had a good view, emphasizing their skill and dedication.

The comments about the crew’s friendliness and willingness to encourage photos create a warm, approachable atmosphere, making the trip more than just a passive viewing — it’s a shared adventure. The ship’s position and the crew’s expertise make this a standout option for those seeking a more intimate, less crowded way to enjoy the show.

The Sum Up: Who Is This Tour Best For?

This Chicago Air & Water Show tour is perfect for families, couples, or groups who want to enjoy the spectacle from a comfortable, scenic vantage point. If you value stunning lake and skyline views blended with the excitement of the show, this option offers an ideal mix of relaxation and entertainment. It’s especially suited for travelers looking for a more exclusive experience that avoids the chaos of land-based viewing.

Those who appreciate attentive service and a knowledgeable crew will find the added touch of professionalism reassuring. Keep in mind the non-refundable policy and plan your trip accordingly, but rest assured that this tour delivers on its promise of excellent views and a memorable day on Lake Michigan.

FAQs

How early should I book this tour?
Most travelers book about 10 days in advance to secure their spot, especially during peak summer months.

What is included in the price?
Your ticket covers the boat cruise, two sailings, and admission to the Air & Water Show.

Is the tour suitable for children?
Yes, the crew is friendly and encourages family involvement. Activities like hoisting sails are part of the experience.

Can I participate in activities onboard?
While most of the experience is passive viewing, crew members sometimes involve guests in fun activities such as sailing maneuvers or taking photos with the captain.

Is the tour weather-dependent?
Yes, like all outdoor activities, it depends on weather conditions. The tour might be delayed or canceled in case of severe weather, but the company emphasizes safety.

What should I bring?
Bring a camera, sunglasses, and sunscreen. Dress comfortably and be prepared for some wind on the water.

How long does each sailing last?
Each sailing runs for about 2 hours and 30 minutes, with the main viewing near show center during the second sail.

Where does the tour start and end?
It begins and ends at The Original Rainbow Cone in Chicago, a convenient meeting point.

Are there any physical activity requirements?
Moderate physical fitness is recommended, as some walking and standing may be involved, but the boat is accessible.

What happens if the show is delayed or runs late?
The crew may extend or delay parts of the tour to ensure you see the main event, but the tour is non-refundable if plans change.

This boat tour offers a refined, comfortable way to enjoy one of Chicago’s most anticipated events. With excellent reviews and a focus on prime views, it’s a smart pick for anyone wanting a memorable, scenic experience on Lake Michigan during the Air & Water Show.