Tours & Activities in Chicago

A family-friendly introduction to Chicago's magnificent architecture

Cruise down the Chicago River and see the city’s most spectacular landmarks on a boat cruise with live, family-friendly commentary and a full-service bar on board.

Take an exciting educational adventure aboard Tall Ship Windy with this cruise from Navy Pier in Chicago. Watch as Great Lakes history and maritime traditions come to life.

See the sights of Chicago from Lake Michigan on this sightseeing lake cruise. Admire stunning views of the Chicago skyline and see many of the city’s iconic landmarks.

See the Chicago skyline from Lake Michigan and enjoy a guided tour of the city

Who let the dogs out? Cruise along the water on the cutest boat trip in Chicago!

Experience Chicago’s legendary architecture from the best seat in the house: the river. Enjoy a comprehensive tour with a live fun guide as you navigate through the heart of the city covering all 3 branches of the Chicago River.

Watch the sun slowly set behind the city from the tranquil waters of Lake Michigan on this serene and romantic cruise. Toast the end of the day with a glass of wine, ice-cold beer or hand-crafted cocktail.

Marvel at Chicago's iconic architecture from the water

Take America's most popular river cruise and see Chicago's epic skyline

Set sail on the Chicago River and Lake Michigan and see the Second City by night

Discover downtown Chicago, as well as some nearby neighborhoods on a minibus tour. Choose to add an architectural cruise of Chicago for the best way to see Chicago from both land and water.

Cruise along the Chicago River on a 60- or 75-minute tour, and discover hidden architectural gems among the city’s renowned landmarks. Led by a docent providing live narration, the tour passes more than 40 structures and sails under historic bridges.

Get up-close and personal to the epic Navy Pier fireworks display every Wednesday & Saturday during the Summer. Choose between viewing from either the Chicago River or Lake Michigan.

USA Today Readers' Choice 2021 Awards #1 boat tour in North America!

Watch the fireworks dance over Chicago's skyline during this speed boat tour

Watch the fireworks dance over Chicago's skyline on this popular 60-minute speedboat tour. Enjoy panoramic views of a magnificent fireworks display from the waters of Lake Michigan. Perfect for a romantic evening or a memorable night out with friends.

Enjoy Chicago's iconic skyline with an exciting speedboat tour departing from Navy Pier. View Chicago's unique architecture and famous landmarks from the water as you listen to the live narration.

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

When in Chicago, cruising down the Chicago River is a must. Except with us, you’ll be taking in the architecture of the buildings that line the beautiful river. We provide detailed explanations of the construction and history of over 50 significant buildings, wrapping up at the end of the river. The Chicago River Cocktail Cruise allows you to experience an architecture tour with a cocktail in your hand!

Dine aboard the Spirit of Chicago and enjoy an extensive buffet meal while cruising down the lakefront. Dance to the onboard DJ or play exciting games like giant Jenga and shuffleboard.

This Wine & Cheese Cruise is a world class Chicago experience for locals and visitors. Board our famous tour boats at Michigan Avenue, and enjoy the Chicago River and Lake Michigan while tasting wine and cheese pairings. There is also a full service bar and climate controlled cabin on the vessel's lower deck. This activity does not have a narrated tour but features light music during the cruise.