Tall Ship Windy, Chicagoland Travel Guide

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Experience the magic of sailing on Lake Michigan aboard the Tall Ship Windy, where adventure and history sail hand in hand.

Embark on a captivating sailing journey aboard the Tall Ship Windy in Chicago. Experience the thrill of the open water while enjoying stunning skyline views, guided by knowledgeable crew members. Perfect for tourists seeking a unique and memorable adventure on Lake Michigan.

A brief summary to Tall Ship Windy

600 E Grand Ave, Chicago, Streeterville, Illinois, 60611, US
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Monday 10 am-7 pm
Tuesday 10 am-7 pm
Wednesday 10 am-7 pm
Thursday 10 am-7 pm
Friday 10 am-7 pm
Saturday 10 am-7 pm
Sunday 10 am-7 pm

From Eve

Know before you go

Hi, I'm Eve. Here are a few practical things to know before exploring Tall Ship Windy.

Book your tickets in advance, especially during weekends and holidays, to secure your spot.
Dress in layers; the weather can change quickly on the water.
Arrive at least 30 minutes early to enjoy the pre-boarding experience and take photos.
Consider a sunset sail for a romantic and picturesque experience.
Don’t forget to bring your camera to capture the stunning views of the Chicago skyline.

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Other nearby places you may find interesting

The closest places of the same kind, if this one is not quite what you had in mind.

Navy Pier

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Explore Tall Ship Windy on the Map

A handpicked selection of must-see spots near Tall Ship Windy, mapped for you.

Getting There

Car

If you're driving from downtown Chicago, head east on E Randolph St toward N Michigan Ave. Continue straight to stay on E Randolph St. Turn left onto N Lakeshore Dr, then take the first right onto E Grand Ave. Continue on E Grand Ave for about 0.5 miles. The Tall Ship Windy will be on your right at 600 E Grand Ave, just past the Navy Pier.
Public Transportation - Bus

From the nearest 'L' station, take the Red Line train north to the State & Lake station. Exit the station and walk to the bus stop on State St. Board the #66 Chicago Ave bus heading east. Ride for about 10 minutes until you reach the stop at Grand & Wabash. From the bus stop, walk east on Grand Ave for about 5 minutes. The Tall Ship Windy will be on your left at 600 E Grand Ave.
Public Transportation - 'L' Train

Take the Red Line train from your nearest station and head towards Howard. Get off at the Grand station. Exit the station and walk east along Grand Ave for about 10 minutes. After you pass the intersection with N Streeter Dr, the Tall Ship Windy will be on your right at 600 E Grand Ave.

Discover more about Tall Ship Windy

Nestled along the picturesque shores of Lake Michigan, the Tall Ship Windy offers an unforgettable sailing experience that captures the essence of Chicago's maritime charm. As you step aboard this majestic vessel, you’ll be transported back to a time of grand sailing ships, complete with billowing sails and a friendly crew eager to share the history and stories of the lake. Guests can enjoy a variety of sailing tours, ranging from relaxing afternoon voyages to exhilarating sunset sails that showcase the breathtaking skyline of Chicago. Each voyage is accompanied by informative commentary from the crew, providing insights into the city's landmarks and the nautical heritage that defines its waterfront. The ambiance on board is both festive and relaxed, making it an ideal outing for families, couples, and solo travelers alike. Don't miss the opportunity to capture stunning photos as you glide along the water with the wind in your hair and the sun on your face. With a schedule that typically runs from late spring through early autumn, Tall Ship Windy is not just a boat tour; it’s an essential part of experiencing Chicago's vibrant culture. Whether you’re a seasoned sailor or a first-time visitor, this adventure promises memories that will last a lifetime.