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Where To Enjoy the Chicago Skyline From the Water

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Chicago might be The Windy City, but it's also got lots of water. During the 1800s, Chicago's canals and rivers made it easy to transport people, livestock, and goods, helping early settlers build one of the largest cities in the United States. Today, the waterways provide amazing views of Chicago's skyline. If you've ever wanted to see our beautiful city from the water, you're in luck. Many cruise companies operate trips in the Chicago area on both the Chicago River and Lake Michigan. Keep reading to find out about some of the best Chicago boat tours.

Chicago Skyline Sail on Tall Ship Windy

The Chicago Skyline Sail's boat tour on the Tall Ship Windy schooner allows you to see the skyline from Lake Michigan and experience life on a topsail. Built in 1996, Windy is a four-masted schooner with room for 150 guests on daytime cruises and 36 for overnight cruises, where passengers sleep in dorm-style cabins. The ship combines traditional construction with a touch of modern technology, like a diesel engine and plumbing. Windy launches from the Navy Pier's South Dock, close to the Shakespeare Theater. All the cruises offered in the Chicago Skyline Sail category last 75 minutes.

There are several cruise options on Tall Ship Windy's Chicago Skyline Sail. Twice a day, the ship takes an Architecture and Skyline Sail, which focuses on iconic buildings on the waterfront and features an educational program about the history of Chicago. The Pirates and Maritime Stories sail, which happens once a day, features stories about real-life pirates who sailed on Lake Michigan. Finally, the Sunset and Skyline Sail takes place at sunset, so you can see the waterfront gleaming in the setting sun. Here are the ticket prices for Tall Ship Windy's Chicago Skyline Sail:

  • Ages 13 and over: $39 for standard boarding, $49 for VIP Captains Boarding.
  • Ages 12 and below: $29 for standard boarding, $39 for VIP Captains Boarding.


Chicago Holiday Cruises by Hornblower

If you've got family in town for a special day, why not treat them to a tour of the city from the water? Chicago Holiday Cruises by Hornblower offers themed boat tours for visitors of all ages. Some of these cruises focus on a specific holiday, like Thanksgiving, Father's Day, or New Year's Eve. Other cruises give you a front-view seat to enjoy city events, like the bi-weekly fireworks show at Navy Pier that runs from Memorial Day through Labor Day.

While these cruises tend to be pricier than the other options, they usually include a gourmet meal and other perks, like a live DJ. For example, the Mother's Day Brunch Cruise usually features a full brunch buffet with unlimited coffee, tea, and water, with cocktails available for purchase. While the prices for Hornblower's Holiday Cruises vary by holiday and cruise type, they may typically range from $37 for a one-hour speedboat tour to $300 for a premier experience comprising a multi-course meal, a live DJ, and an open bar.

Chicago Architecture Foundation Center River Cruise

One of Chicago's most popular boat tours, the Chicago Architecture Foundation Center River Cruise combines beautiful scenery with expert insight into the city's most beloved historic buildings. It's hosted by the Chicago Architecture Foundation (CAF), a nonprofit organization that also runs the Chicago Architecture Center. A trained volunteer docent leads each 90-minute cruise and provides commentary about the history of each district you pass. The CAF partners with First Lady Cruises for this experience, so each tour takes place on board one of the fleet's luxury cruisers.

Suppose you want to learn more about Chicago's architectural history. In that case, you can bundle your ticket with a discounted admission ticket to the Chicago Architecture Center, valid for seven days after your cruise. While guests of all ages can ride the tour, the CAF recommends it for guests ages 12 and older. The tour launches several times a day, with an evening option on most days. The evening tour includes a full-service bar, so you can purchase beer, wine, or cocktails to pair with the sights. Here are the ticket prices for the CAF Center River Cruise:

  • Adults: $51.96 for a daytime cruise and $55.74 for an evening cruise.
  • Infants: $23.62.


Mercury Chicago by Night! Cruise

Suppose you want to see the city lights of Chicago from the water, the Mercury Chicago by Night! Cruise might be the boat tour for you. This cruise, like all of Mercury's boat tours, passes through the Chicago Harbor Lock as you travel from the Chicago River into Lake Michigan. The route takes you through Chicago's historic riverfront neighborhoods, and you'll pass the Merchandise Mart, Marina City, the Wrigley Building, and many other iconic buildings. After entering Lake Michigan, you'll see the Chicago Harbor Lighthouse before returning to shore.

As you pass key landmarks, your guide will tell you all about the history of each building and explain its role in Chicago's development. You can also buy food from the boat's onboard concession stand, including snacks and canned cocktails. With both covered and uncovered viewing areas, the ship usually continues to serve guests on rainy nights, though rough weather might cause cancelations. Mercury's boarding area is on East Wacker Drive on the Riverwalk. Here are the ticket prices for the Chicago by Night! Cruise:

  • Adults ages 16 and over: $45.
  • Children ages 5 to 15: $20.
  • Children under 5: Free with an adult ticket.


Did we miss your favorite Chicago boat tour? Do let us know. Whether you're looking for a family-friendly trip around Lake Michigan or an unforgettable date night experience with someone special, Chicago is the perfect setting. Let Automatic Appliance Parts Corporation help you in your everyday appliance repair so you can kick up your feet on your boat tour without thinking about that washer or dryer that needs fixing. Our appliance part lookup tool allows you to search for the exact part you need to fix your appliances quickly and easily.