Chicago might be known for its wind, but it’s also famous for something else – it’s water!

Set on the picturesque shores of Lake Michigan (one of the five Great Lakes) and with the network of rivers and canals that weave their way through the city, there is water practically everywhere you look in Chi Town.

That’s why Chicago is a great place to explore by cruise.

In fact, I dare say that seeing the third largest American city from the water is a must.

From dinner and sunset cruises to boat tours that will teach you all about the city’s historic landmarks, continue reading for the 12 best Chicago cruises for dinner, sunsets, and tours.

1. Lake Michigan and Chicago River Cruise by Speedboat

Adventure, relaxation, and sightseeing all in one!

This Lake Michigan and Chicago River Cruise will allow you to experience the city from a new perspective.

The tour begins with a calm ride along the Chicago River.

During this portion of the tour, you’ll learn about the city’s history and its famous skyscrapers.

For the grand finale, you’ll hop on a speedboat that will have you whizzing around Lake Michigan.

You’ll also get some incredible views of the Chicago skyline.

Tour details

  • Duration: 1 hour 15 minutes
  • Departure Point: 600 E Grand Ave, Chicago
  • Inclusions: Entry fees, all taxes, architectural tour and speedboat ride

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2. Chicago Odyssey Dinner Cruise

Set sail on the Odyssey.

Discover Chicago’s incredible skyline at night on this luxury dinner cruise.

Aboard this sleek yacht, you’ll find a newly renovated rooftop lounge, chic atmosphere, and stylish interior.

Sit down at your private table and enjoy a three-course plated meal of celebrity chef-inspired dishes.

All meals are prepared fresh on board and there are vegetarian options available.

After dinner, it’s time to hit the dance floor!

A DJ will be spinning tracks all night long so you can dance the night away with the backdrop of Lake Michigan and the Chicago skyline behind you.

Tour details

  • Duration: 3 hours
  • Departure Point: Navy Pier
  • Inclusions: 3-course dinner, unlimited coffee, tea, and water, on-board DJ and entertainment, local taxes and fees, service charges

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3. Chicago Odyssey Brunch Cruise

Do you prefer to cruise during the day?

Chicago Odyssey has this option too and you can enjoy Chicago’s skyline while snacking on a delicious brunch.

Coffee and tea are available on board so you can sip on a cuppa as you glide past the most popular landmarks.

Attractions you’ll see include Sears Tower, the John Hancock Tower, Navy Pier and Adler Planetarium.

Have your camera ready as you snap photos of friends and loved ones with Chicago and crytal waters in the background.

  • Departure Point: 600 E Grand Ave, Chicago, IL 60611, USA
  • Departure Time: 1pm
  • Duration: 2 hours

4. Private Chicago Sunset Sail on Lake Michigan

Glide along Lake Michigan on this private sailing tour in Chicago.

This two-hour sailing experience is completely private, meaning it’ll be just you and your partner, family, or friends, alongside the captain.

As you’re on a private charter, it’s up to you to set the itinerary!

You can ask the captain to take you wherever you want to go.

Rest assured, wherever you sail on Lake Michigan will offer incredible views of the open lake, as well as of the Chicago skyline.

Charters are available for up to 6 people.

Tour details

  • Duration: 2 hours
  • Departure Time: 6:00 pm
  • Departure Point: Monroe Harbor, Illinois
  • Inclusions: 1 bag of ice, captain services, local taxes, private sailing charter

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5. Spirit of Chicago Sunset Dinner Cruise with Buffet

Party it up on this sunset Chicago dinner cruise!

Spend an evening dining, dancing, and sightseeing on this all-inclusive tour.

An elegant dining room with a dinner buffet (vegetarian options available) is open to all guests.

There will also be a DJ on board throughout the night so you can dance all night long.

To top it off, the cruise will sail past some of the city’s biggest landmarks.

You can expect to catch a glimpse of Navy Pier, Soldier Field, and much more!

Tour details

  • Duration: 3 hours
  • Departure Point: Navy Pier
  • Inclusions: Dinner, live entertainment

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6. Chicago Wine Tasting Cruise

Wine tasting by boat? Yes, please!

See the sites and gain a unique perspective on the city, all while indulging in some local wine.

Staff from nearby Lynfred Winery will be on board to provide tastings and teach you all there is to know about their delicious wines.

This cruise features both a short wine course and generous tastings of Lynfred wines.

Throughout the 90-minute cruise, remember to look out the windows!

You’ll pass by over 40 of the city’s most distinct buildings, including the Willis Tower and the John Hancock Center.

Tour details

  • Duration: 1 hour 30 minutes
  • Departure Time: 7:00 pm
  • Departure Point: 600 E Grand Ave, Chicago
  • Inclusions: Wine tastings, light refreshments, cash bar available

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7. Chicago River and Lakefront Night Cruise

There’s nothing quite like Chicago at night.

The Windy City comes alive at nightfall, illuminated for all to see.

This evening lakefront cruise will put you right in front of the action.

Enjoy panoramic views of Chicago’s famous skyscrapers and Buckingham Fountain’s mesmerizing lights display.

Throughout the tour, there will be live commentary to teach you about the history of the city.

Each guest will also be given a “neon light wand” to make you feel like part of the sparkling magic.

Tour details

  • Duration: 1 hour 30 minutes
  • Departure Time: 8:15 pm
  • Departure Point: 112 E Wacker Dr, Chicago
  • Inclusions: All taxes and fees, live commentary

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8. Chicago Architecture River Cruise

The Chicago River is a sight to behold.

With the many canals and rivers that it makes up, you could spend a whole afternoon exploring these waterways.

This 75-minute boat tour aims to show you all the highlights of the Chicago River.

Specifically, the Chicago River is the best way to see some of the city’s most famous skyscrapers.

The rivers weave their way right through the downtown core of the city, meaning if you look in any direction, you’ll be treated to some stunning architecture.

You’ll pass by over 40 notable buildings, including the Sears Tower, the Wrigley Building, and the Post Office Building.

Tour details

  • Duration: 1 hour 15 minutes
  • Inclusions: Live commentary, guided architecture cruise

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9. Chicago Architecture Lakeside Tour

Have you ever wanted to board a pirate ship?

Now’s your chance!

This Chicago Lakeside Architecture tour will have you boarding the city’s Official Tall Ship.

This historic boat is the best way to explore Chicago’s skyline.

From the city’s maritime roots to modern science and technological advances, you’ll learn plenty of fun and informative facts about the Windy City.

You’ll also learn all about Lake Michigan, a natural wonder.

Tour details

  • Duration: 1 hour 15 minutes
  • Departure Point: 600 E Grand Ave, Chicago
  • Inclusions: All taxes and fees, live audio commentary, entry fees

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10. Chicago Land and River Architecture Tour

Experience Chicago by land and water on this all-in-one Chicago Land and River Architecture Cruise.

This comprehensive tour will show you everything Chicago has to offer.

So if you’re only in the Windy City for a short time, this is the tour for you.

Your tour will take you to the city’s North and South sides, as well as along the Chicago River.

To kick things off, you’ll board a coach or trolley and exploring the many diverse neighborhoods that make up the city of Chicago.

From there, you’ll board a 90-minute river cruise that will teach you all about Chi Town’s famous architecture.

Tour details

  • Duration: 3 hours 30 minutes
  • Departure Point: 17 E Monroe St, Chicago
  • Inclusions: All taxes, narrated trolley or coach tour, Chicago architecture cruise

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11. Architecture River Cruise and Chicago Helicopter Tour

Experience Chicago from two unique perspectives on this Architecture River Cruise and Chicago Helicopter Tour.

First, you’ll float along the Chicago River.

Here, you’ll take in the sites from the water and learn about the history of Chicago’s most famous skyscrapers, as well as its most famous architects.

After your cruise ends, you’ll board a state of the art helicopter.

From up above, you’ll have incredible panoramic views of the city – so don’t forget to bring your camera!

You’ll be able to spot everything from Wrigley Field to Willis Tower to Lake Michigan.

Tour details

  • Departure Point: 2420 S Halsted St, Chicago
  • Inclusions: Entry fees, 75-minute river cruise, live commentary, all taxes and fees, helicopter flight

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12. Chicago Architecture Fireworks Cruise

Chicago is known for its architecture, so learning about the city’s historic skyscrapers is a must.

The best way to see them is by boat, and this tour kicks off with a 90 minute cruise ride.

Your evening cruise will navigate the Chicago River, giving you a magical view from down below.

As if it could get any better, this unique tour ends with pyrotechnics!

Navy Pier is famous for its incredible fireworks displays in the summertime.

Catch the fireworks extravaganza from abroad your cruise, the best viewing point in the city!

Tour details

  • Duration: 1 hour 30 minutes
  • Departure Point: 600 E Grand Ave OR 401 N Michigan Ave
  • Inclusions: Live commentary, Navy Pier fireworks, 90-minute guided tour

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We hope this list has convinced you that exploring Chicago by water is pretty much a rite of passage.

Whether you prefer a romantic sunset dinner cruise or an informative architectural tour, there is a Chicago cruise for everyone.

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Emily is a freelance writer from Canada and it was during her time studying History that she became interested in travel. Countries I've visited include the United States, Mexico, the Cayman Islands, New Zealand, Costa Rica, the United Kingdom, Greece, Spain, Portugal, Italy, France, Germany, Sweden, Poland, Austria, Belgium, the Netherlands, and Switzerland.