Top Chicago Cruises and Boat Tours

Best Lake Michigan Cruises and River Cruise Chicago

Chicago is blessed with ocean like Lake Michigan and Chicago River passing through downtown Chicago. Thanks to miles long Lake Michigan waterfront and Chicago River, we have plenty of water activities including lake cruises, boat tours and river cruise Chicago for entertainment during summer months and later in fall season considering weather conditions.

I have come up with the list of popular Chicago cruises, sailing and water tours that can be useful for planning your summer activities in Chicago.

Chicago Cruises

We have different kinds of options available for Chicago cruises including brunch cruise, lunch cruise, dinner cruise, sunset cruise, daytime cruise and nighttime cruise.

There are many Chicago cruise companies including popular Odyssey and Spirit of Chicago. Hop on one of these Chicago cruises to enjoy the lakefront and breathtaking views of Chicago skyline from the water.

I also recommend to experience our windy city from Chicago river by sailing on river cruise Chicago!

Chicago Brunch Cruises

Chicago Brunch Cruise

Chicago Odyssey Lake Michigan Brunch Cruise

Perfect way to relax and enjoy brunch on Lake Michigan. Chicago Odyssey Lake Michigan brunch cruise departs from Navy Pier. This Chicago brunch cruise gives you 2-hours of sailing on Lake Michigan along with brunch buffet and live DJ entertainment.

You will have great opportunity to enjoy the breathtaking views of Chicago skyline from the climate controlled deck.

Enjoy mimosa while capturing Chicago’s skyline pictures.

Book Cruise @ Viator

Lunch Cruise Chicago

Chicago Odyssey Lake Michigan Lunch Cruise

Enjoy 3-course gourmet meal on luxurious yacht departing from Navy Pier. It is 2-hour lunch cruise featuring climate controlled observation deck.

Chicago lunch cruise is one of the best ways to enjoy scenic city skyline from the deck. Make sure to carry your camera to capture high quality, memorable photographs.

Book Cruise @ Viator

Spirit of Chicago Lunch Cruise with Buffet

Spirit of Chicago Lunch Cruise is also one of the best and budget friendly option to enjoy lunch while sailing on the Lake Michigan. Like Odyssey Lake Michigan Cruise, this Spirit of Chicago Lunch Cruise features 2 hours sailing with lunch buffet and unlimited nonalcoholic beverages.

Book Cruise @ Viator

Odyssey Chicago River Architectural Lunch Cruise

Want to learn about Chicago’s famous architecture while enjoying the lunch? Try narrated Odyssey Chicago River Architectural Lunch Cruise.

Odyssey Chicago River Architectural Lunch Cruise departs from 455 N City front Plaza Dr, Chicago, IL 60611.

Sail on the Chicago River, learn about the architecture of famous landmarks while enjoying 3-course lunch featuring chicken, salmon and cheesecake. It’s popular river cruise Chicago!

Book Cruise @ Viator

Chicago Dinner Cruise
Photo Courtesy: Viator

Dinner Cruise Chicago

Spirit of Chicago Sunset Dinner Cruise with Buffet

Plan your evening on Lake Michigan with luxurious sunset dinner cruise. Enjoy dinner and breathtaking sunset views of Chicago skyline from the deck. This Spirit of Chicago Sunset Dinner Cruise with Buffet departs from Navy Pier.

Spirit of Chicago Sunset Dinner Cruise features On-board entertainment with DJ music, access to shared spaces, and interactive games.

Book Cruise @ Viator

Odyssey Fireworks Dinner Cruise Chicago

Want to see fireworks from the Lake Michigan? Hop on Chicago Odyssey Fireworks dinner cruise to enjoy the breathtaking views of the fireworks display. This 3 hours long Chicago dinner cruise features 3-course meal, rooftop lounge along with live DJ entertainment.

One of the best way to relax on the rooftop lounge to enjoy the Chicago skyline and Chicago fireworks display.

Book Cruise @ Viator

Odyssey Chicago River Dinner Cruise

Enjoy 3-hour long Chicago River dinner cruise and explore famous landmarks such as Willis Tower and Tribune Tower. Odyssey Chicago River Dinner cruise departs from NBC Tower at 455 N. Cityfront Plaza Dr, on the north side of the River Esplanade between Columbus Drive and Michigan Avenue.

Chicago River dinner cruise features 3 course meal with unlimited nonalcoholic beverages and on board Dj entertainment. It’s popular river cruise Chicago!

Book Cruise @ Viator

You may also like Odyssey Dinner Cruise in Chicago!

Day Cruise Chicago

Chicago Architecture Cruise First Lady
Photo Courtesy: First Lady Cruiseline
Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady

The Chicago Architecture Foundation Center River Cruise by First Lady Tour Company is highly rated architecture tour. This 90-minnute long Chicago architecture boat tour is the number one tour among all architecture cruises.

I recommend this Architecture Tour to first time visitors in Chicago. I would say visit to Chicago is not complete without experiencing the Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady Cruise company.

The Chicago Architecture Foundation Center River Cruise by First Lady Cruise Company is scheduled to depart from 112 E Wacker Dr, Chicago, IL 60601, USA.

Book Cruise @ Viator

Wine Tasting Cruise Chicago

If you are having a long week or spending a full day exploring Chicago, hop on 90 minutes long, relaxing wine tasting cruise and sail past Chicago’s most popular landmarks while enjoying local wines.

Chicago Wine Tasting Cruise departs from the Navy Pier.

Tuesday Night Sunset Happy Hour Cruise aboard the Mystic Blue Yacht

Relax and enjoy Tuesday night sunset Happy Hour Cruise on one of the biggest yacht in Chicago. This 2 hours and 30 minutes long Happy Hour Cruise departs from Navy Pier. You must be 21 or older to be eligible to aboard the yacht party.

In my opinion, this Happy Hour cruise is one of the best Chicago cruises and perfect to hang out with friends or co-workers after work.

Book Cruise @ Viator

Private Day Sailing Excursion on Lake Michigan

Love to sail on a private sailboat? You will have great time sailing on Lake Michigan for 2 hours with this sailing excursion. Sailboat can accommodate up to six passengers at a time.

This sailing excursion on Lake Michigan is BYOB, no glass containers allowed. Sailboat features captain and crew for the duration of the tour and comes with ice and fridge for your drinks.

Guests can enjoy their favorite music on Bluetooth enabled music system. You can customize your sailing itinerary based on your group’s interest.

They also have option for Private Sunset Sail on Lake Michigan tour, best way to enjoy nighttime views of Chicago downtown from the Lake Michigan along with sparkling lake water.

Book Cruise @ Viator

Chicago Cycleboat Tour on the Chicago Riverwalk

Chicago Cycleboats Tour – Unique Way to Experience the Chicago River

Experience the Chicago River differently with 90 minutes long Cycleboats tour. It’s 90 minutes long group tour that holds total 16 passengers -10 paddlers and 6 riders. Chicago Cycleboats Tour is BYOB.

Chicago Cycleboats Tour departs from the Chicago Riverwalk between the Wells Street and LaSalle Street bridges.

Lake Michigan Speedboat Tour

If you love speed then you will love this exhilarating Seadog speedboat tours ride along Chicago’s famous Lake Michigan. Feel the thrill of the 2000-horsepower engine as you cruise on your speedboat on the beautiful lake.

Undoubtedly, Lake Michigan Speedboat tour is one of the best ways to enjoy the fabulous views of Chicago from the Michigan lake. Overall, lakefront speedboat ride is one of the best tours in Chicago during summer season.

Book Tour @ Viator

Fireworks Cruise Chicago
Photo Courtesy: Viator

Night Cruise Chicago

Chicago by Night (90 minute River and Lakefront Cruise)

Enjoy breathtaking nighttime views of Chicago’s city skyline from the Lake Michigan and the Chicago River. Chicago by Night River and Lakefront Cruise is one of the best ways to learn about the history from the guide when you sail past famous landmarks including Museum Campus, Willis Tower, John Hancock Building and more.

Chicago by Night River and Lakefront Cruise departs from 112 E Wacker Dr, Chicago, IL 60601

Book Cruise @ Viator

Private Navy Pier Fireworks Sail in Chicago

Alike Private Sailing Tour, this Fireworks Sail in Chicago tour is perfect way to watch Navy Pier fireworks from the lake. Enjoy nighttime views of Chicago skyline and beautiful fireworks from Navy Pier.

Book Cruise @ Viator

Chicago Sailing Trips

Chicago Friday Photo Tall Ship Windy Chicago

Tall Ship Windy: Real Pirates of the Inland Seas Sail

Learn about the Lake Michigan’s popular pirate stories while enjoying Chicago’s skyline views from the lake. It’s one of the best cruises for families with children. You will be surprised to learn about the battles and treasures that happened right here on Lake Michigan.

Book Cruise @ Viator

Now, as you have the list of popular Chicago cruises, boat tours and sailing trips, plan your weekend or after work activities to experience the breathtaking views of our windy city from the Lake Michigan and the Chicago River.

Visiting Chicago for the first time? Read my What to Pack for Chicago guide before arriving to Chicago.

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Hi, I'm Victor Sevale - My goal is to share information on everything I see, do, eat and drink in Chicago. Let me inspire you to explore Chicago more with reviews, photographs, and useful tips from my personal experience.

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