1. Chicago Architecture River Cruise

9660+ reviews

On this boat tour, you will have the opportunity to cruise down the Chicago River and see the city’s famous architecture. Your onboard guide will provide commentary as you watch the breathtaking skyline pass by, featuring over 40 notable buildings such as Navy Pier, the Wrigley Building, and the John Hancock Building. You will also travel along all three branches of the Chicago River, passing by landmarks such as the East Bank Club, the old Post Office Building, and the Willis Tower (formerly known as the Sears Tower).

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2. 90-Minute Chicago River Architecture Tour

2797+ reviews

A Chicago River cruise is the perfect way to discover the architectural gems of the Windy City from a convenient and ideal vantage point. This leisurely excursion, which is offered several times throughout the day, allows you to easily fit it into your itinerary. During the tour, you will have the chance to see over 130 years of architectural history and explore a large portion of the city without the need for taxis or public transit.

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3. Chicago Lake and River Architecture Tour

1050+ reviews

Take a comprehensive cruise that showcases the history of Chicago’s architecture by boarding a boat. During the tour, you will be treated to views of the Chicago skyline while receiving architecture-focused commentary that highlights each of the landmark buildings. You will also have the opportunity to snap photos of yourself and your group against the stunning 26-mile shoreline of Lake Michigan.

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4. Lake Michigan Sightseeing Cruise

525+ reviews

During this Lake Michigan sightseeing boat cruise, you will have the opportunity to take in iconic views of the stunning Chicago lakefront and its numerous landmarks. Climb aboard your vessel for a leisurely ride and soak in panoramic views of the Windy City’s skyline from a unique perspective. As you cruise along, you will listen to informative commentary and see landmarks such as the John Hancock Center and Willis Tower, among others. You are welcome to bring your own lunch or grab a drink at the onboard bar during the ride.

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5. Chicago Sunset Cruise

500+ reviews

Experience a unique perspective of the Windy City by going on an evening 1.5 hour cruise, which is perfectly timed to coincide with the sunset. Board your open-top vessel in the heart of the Magnificent Mile and take a cruise along the Chicago River with a guide who will point out architectural highlights. Afterward, see the skyline from a distance and watch the skyscrapers light up as you continue to Lake Michigan for a sunset viewing.

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6. 45-Minute Chicago River Architecture Tour from Magnificent Mile

345+ reviews

On this 45-minute architecture cruise, you will have a front row perspective of the stunning buildings that line the Chicago River. That family-friendly tour includes live commentary about the history and architectural heritage of Chicago and highlights landmarks such as the Chicago Riverwalk, Michigan Avenue Bridge, Wrigley Building, and Willis Tower. Choose to sit on the open-air top deck or the sheltered bottom deck for the ultimate view of Chicago.
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7. 30 Minute Lake Michigan Speedboat Ride

190+ reviews

Experience the thrill of speeding along the shoreline of Lake Michigan as you pass by iconic landmarks in Chicago on this high-speed boat ride. Climb aboard your 2,000 horsepower speedboat at Navy Pier and hold on tight as you speed past the Willis Tower, Grant Park, and Buckingham Fountain, taking in the history and architecture of the city as you go. This exciting tour starts and ends at Navy Pier.
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8. Educational Tour and Sail Aboard Chicago’s Official Flagship Windy 148′ Schooner

45+ reviews

See Chicago’s iconic architecture from a different perspective during this sailing tour. As you sail along the shoreline, your guide will provide commentary on the people, events, and efforts that have shaped the city’s architecture. You’ll learn about the rich maritime history of Chicago as well as its modern contributions to science and technology. This tour offers the opportunity to take stunning photos and offers departures in the afternoon or early evening. Relax and take in the sights as you sail.
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9. Chicago Fireworks Dinner Cruise with Buffet

40+ reviews

Treat yourself to a unique and memorable evening on Lake Michigan with this dinner, dancing, and sightseeing cruise. Begin your journey at Navy Pier and take in the stunning views of Chicago’s skyline as the sun sets. Onboard, enjoy an all-you-can-eat buffet dinner, drinks available for purchase, a DJ-led soundtrack, and even a fireworks display (weather permitting). Make your own way to the pier to start this one-of-a-kind night out on the lake.
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10. Premier Chicago River Dinner Cruise

30+ reviews

Take in the sights of Chicago in style on this 3-hour dinner cruise on the Odyssey. Admire the city’s stunning architecture and views as you sail down the Chicago River through the ship’s panoramic windows. Savor a delicious 3-course meal while being entertained by a DJ. A full-service bar offering microbrews, cocktails, and a selection of wines is available for purchase to complete your experience.
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