Top Chicago Cruises &amp; Sailing - page 2

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

2 hoursFree Cancellation

from $105

Get the most out of your trip to Chicago as you enjoy discount access to five of the city’s top attractions with the CityPASS®. This easy-to-use mobile ticket grants you free entry into top-tier sights including the Chicago's most famous aquarium and Skydeck Chicago, plus your choice of admission to three of the following attractions: Field Museum, Art Institute of Chicago, Museum of Science and Industry, 360 CHICAGO Observation Deck, Adler Planetarium, or Shoreline Sightseeing Architecture River Tour.

from $144

City Cruises: Chicago Fireworks Premier Dinner Cruise

2 to 3 hoursFree Cancellation

from $150

Zoom along the shoreline of Lake Michigan, zipping past famous landmarks as you go, during this exhilarating speedboat ride in Chicago. Climb aboard your 2,000-horsepower speed boat at Navy Pier, then hang on for the ride of a lifetime, as you zip past famous attractions like the Willis Tower, Grant Park, and Buckingham Fountain, pausing to learn a little about the history and architecture of the Windy City along the way.

Lake Michigan 30-Minute Speedboat Ride

4.1

(335)

30 minutesFree Cancellation

from $36

Skip navigating around the city with a map and guidebook and explore Chicago's iconic landmarks in just a few hours on this sightseeing tour led by an expert guide. Board a comfortable, large-windowed minibus and explore Downtown and North Side neighborhoods, stopping to visit several locations and hear about the historical and cultural factors that make Chicago unique. Upgrade your tour with a popular open-top boat tour on the Chicago River that focuses on the city's renowned architecture.

Chicago City Tour with Architecture River Cruise Option

4.8

(716)

2 to 4 hoursFree Cancellation

from $50

4.7

2 to 8 hoursFree Cancellation

Chicago City Tours

from $199

Enjoy a celebratory way to sightsee—and a river cruise like no other—with this evening excursion along the Chicago River. Your modern, glass-enclosed boat makes for a comfortable ride, no matter the weather—and gives panoramic views of Chicago’s well-known architectural gems. As you go, indulge in a gourmet, multi-course meal while enjoying live entertainment, including a DJ and fireworks displays on Wednesdays and Saturdays.

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

(5)

2 to 3 hoursFree Cancellation

from $123

Skip the corny jokes and never-ending speeches — our shared tours are built for travelers who want the real Chicago, not a stand-up routine. ✔️ Over 20 iconic stops ✔️ Zero wasted time ✔️ Only the best views, landmarks, and photo spots We don’t stall, we don’t drag things out — and when we say “See All of Chicago,” we mean it. From skyline views and lakeside gems to architectural icons and hidden local favorites, our guided route is packed with unforgettable stops — and none of the filler. Let’s explore the city — the right way.

Chicago City Tours See It All No Time Wasted

(20)

4 to 8 hoursFree Cancellation

from $150

Get a chance to experience the Windy City from multiple vantage points during this two-hour, small-group boat tour in Chicago. Hop aboard a secure and reliable US Navy-built Rigid Inflatable Boat (RIB) for a unique sightseeing experience. Pass by iconic sights such as Navy Pier, Soldier Field, Fort Dearborn, Vietnam Memorial, Wolf Point, Shedd Aquarium, and more, all while comfortably seated in a group capped at only six people.

Small-Group Sightseeing Boat Tour in Chicago

5.0

(95)

1 hour 30 minutesFree Cancellation

from $89

Set sail on our flagship vessel, where style meets comfort in a Tiki Chic atmosphere. Your adventure begins on the iconic Chicago Riverwalk, where you’ll board a beautifully appointed boat featuring two climate-controlled decks, two full bars, two bathrooms, and both indoor and outdoor viewing areas—perfect for soaking in the sights no matter the weather. As you sip a refreshing beverage, enjoy the rare experience of transiting the historic Chicago Locks—a must-see for locals and visitors alike. Once you glide into the open waters of Lake Michigan, you’ll be treated to breathtaking views of Chicago’s world-famous skyline, framed by the gentle breeze and city lights. Looking to elevate your cruise? Upgrade to the exclusive Admiral’s Lounge, where you’ll enjoy top-shelf spirits, including selections from the Captain’s Private Reserve, all in a more intimate, upscale setting. This is more than just a boat ride—it’s a uniquely Chicago experience you won’t forget!

Chicago Skyline Tiki Chic Party Cruise on Lake Michigan

1 hour 30 minutes

from $35

On A Boat Sailing offers an all-inclusive, private VIP sailing experience departing from the brand-new Navy Pier Marina in Downtown Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the boat rental for you! Amenities on board include: Pricing for private groups up to 7 guests. Custom pricing available for larger groups up to 12. Anchoring in the Chicago Playpen for swim and float parties. Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties. Large open cockpit seating area. Complimentary beverages and snacks or BYO (alcohol allowed). Stereo surround sound speakers with Bluetooth connection. Fridge with ice, fully stocked kitchenware. Skyline views of Downtown Chicago, Navy Pier and the Chicago Lighthouse. Anchoring for concerts at Northerly Island. Kitchen, bathroom and changing room on board.

Navy Pier Chicago Private Sailboat Charter with Captain

3 hoursFree Cancellation

from $1,299

Soak up unbeatable views of Lake Michigan and the Chicago skyline—and stay on the water long enough to watch the lights come on in the city—on this private, sunset sailing tour. This charter is completely customizable, giving you the chance to choose your music, route, and up to five additional guests. Sail into the sunset with your own drinks and snacks (refrigerator and ice on board) and your family or friends by your side, all led by US Coast Guard–certified captain.

5.0

Serene Private Sunset Sail on Lake Michigan - Navy Pier, Chicago

2 hoursFree Cancellation

from $508

Enjoy the most Unforgettable Fireworks Cruise in Chicago! A SPECIAL EVENT SAIL! Treat yourself to Navy Pier’s spectacular fireworks display from the best seats in town! Grab a cool drink from our full bar, relax, and enjoy a leisurely evening sail past the brilliant and beautiful Chicago nighttime skyline. Windy provides the accompanying sound track, over the ship sound system coordinated fireworks display, amazing show! Rain or Shine event. no umbrellas are allowed to be opened underway. Tall Ship Windy, located on Navy Pier, and we have a ticket booth and dock, in front of the Billy Goat Bar and Grill. Arrive early, as fireworks crowds are huge! expect travel delays.

Chicago's Fireworks Show aboard Tall Ship Windy!

4.8

(14)

1 hour 30 minutes

from $114

See Chicago’s legendary Air & Water Show from the best seat in the city! Secure a VIP spot on a Lake Michigan cruise (or Skydeck viewing party) and watch the U.S. Air Force Thunderbirds, Golden Knights, and dazzling stunt pilots soar overhead. Enjoy premium amenities, from fast-track boarding to reserved seating, up-close views, and included food or drinks (per package). With unmatched photo ops and the sound of jets flying overhead, this is a must-see experience for locals and visitors alike—just in time for summer’s biggest Chicago festival. Book early; these shows always sell out fast.

Chicago Air and Water Show VIP Cruise or Skydeck Experience

5.0

(2)

2 hours 30 minutes

from $154

Chase away your Monday blues with Chicago’s coolest concert at sea! Hop aboard the historic Tall Ship Windy for a 2-hour live blues music cruise on Lake Michigan, featuring city skyline views and a rotating roster of top local and international artists. With a full-service bar and plenty of space to move, relax, and dance, this floating music event blends unbeatable atmosphere with legendary sounds—perfect for date nights, group outings, or music lovers looking for a summer highlight. VIP boarding upgrades and kid discounts available. Book early; these shows sell out fast!

Monday Night Concert Series: Blues and Views Aboard Tall Ship

1616

2 hours

from $81

Special Offer

Navy Pier Fireworks Cruise On A Private Sailing Yacht

3 hoursFree Cancellation

Route 66, known as "The Main Street of America", runs through eight states from Chicago to Santa Monica. EN route to Illinois, POR Missouri, Kansas, Oklahoma, Texas, New Mexico, Arizona and California. Along DE way, it connects iconic cities such as St. Louis, Tulsa, Amarillo, Albuquerque, Flagstaff and Los Angeles, offering a unique experience through varied landscapes, from the Midwest Plains to the Southwest Deserts, each with its own history and culture. Route Chicago : 50 points Route DE Chicago to St. Louis : 56 points Route San Luis : 13 points Route DE San Luis to Joplin : 56 points Route Joplin to Oklahoma city : 29 points Route DE Oklahoma City to Amarillo : 27 points Yellow Route to Santa Fe : 39 points Route DE Santa Fe to Las Vegas : 80 points Route DE Las Vegas to Los Angeles : 34 points Total DE DE DE DE l’Or points of interest: 384

Routes POR Route 66 with Audio Guide

6 daysFree Cancellation

from $24

Don't worry about finding your own way to or from the airport: with a private airport transfer service, you can navigate Chicago without worry. Choose between various luxury vehicle options, including an executive sedan, first-class sedan, and SUV, and meet your driver directly at your Chicago address or at your arrival gate. Then, enjoy a stress-free ride through the Windy City directly to your destination.

One-Way Private Airport Transfer by Sedan

4.0

(4)

30 to 45 minutesFree Cancellation

from $179

Historical and Architectural Chicago Fireboat River & Lake Cruise

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Top Attractions in Chicago

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Attractions

What are people saying about Chicago

Robert_R, Apr 2026

The tour was great. Very...

The tour was great. Very helpful and friendly staff. The guide was very knowledgeable (as well as the bartender who recommended some great beers.) The Busse is an amazing boat. It was great to ride in part of Chicago's history while learning about Chicago's history.

Chicago Architectural River Cruise

Heidi_W, Apr 2026

This is the best way to...

This is the best way to acclimate yourself to Chicago. We learned so much from the tour guide and used what we learned all weekend long. The crew was amazing and professional and the complementary drinks especially he hot chocolate was much needed on this cold afternoon.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

chloe_b, Dec 2025

Thank you leslie <3

Leslie made our experience wonderful! We celebrated my girlfriend’s birthday by doing the brunch. Even though it was raining, it was still beautiful! Leslie made sure that our mimosas were filled, the staff was very friendly, and food was delicious. We will definitely be back for another brunch or dinner!

Chicago City Tour with Architecture River Cruise Option

Dawn_G, Dec 2025

Worth it!

Love all the information of the buildings’ history! Seeing them in one area was amazing! The tour took about an hour. I didn’t visit the bar/cocoa area downstairs but it’s great that they have one. The guide was funny and friendly. He interacted with us as well. Once trip was over, he stood by to say bye to everyone. I would do it again!

Chicago By Night River and Lake Cruise

Tracy_V, Oct 2025

Unforgettable!

Absolutely breathtaking!!! Pictures are beautiful but there are no words to describe the night cruise, it’s one of a kind! Book your night cruise, and post your word to describe! Haiku our tour guide was amazing, knowledgeable, funny and friendly! Thank you for sharing Chicago’s history with all of us.

Chicago River 90-Minute Architecture Boat Tour

Noreen_S, Oct 2025

As out of state visitors,...

As out of state visitors, learning about Chicago’s history, and particularly the architecture that has evolved since the Great Fire, was a great introduction to Chicago. The boat tour was a great way to see the city and its history. David was a fantastic docent, extremely knowledgeable, engaging, informative and humorous. Already recommended this to my daughter.

Lake Michigan Sunset Cruise in Chicago

Lauren_T, Oct 2025

Our tour guide, John, was...

Our tour guide, John, was full of energy and provided plenty of knowledge about Chicago history while making it a fun environment. The music was a variety of genres so there is something for everyone. We didn’t purchase any beverages while on the cruise, but they did let us know it was available. Worth the money for sure! Picture worthy.

Small-Group Sightseeing Boat Tour in Chicago

Sian_S, Sept 2025

Outstanding Value

Fantastic trip for a very reasonable price. The host was friendly and knowledgeable and made the trip a real pleasure. We were delighted to find this trip also included the city river tour in the price. One very slight improvement would be to make the location a little better signposted but we would definitely book again.

Chicago CityPASS®

Jeremy_B, Sept 2025

City Pass Fun!

We had a blast! Willis Tower was really cool. Field Museum is massive, it takes a very long time to get through. The aquarium was a hit with everyone. The architecture boat ride was amazing! I wish I could remember it tour guides name. He had such a wealth of knowledge about all of the current, past, and future buildings and he was hilarious to boot. If you do it at sunset you get to see some pretty incredible views of the city. We ran out of time and weren’t able to do all 5 attractions.

City Cruises Chicago: River Architectural Lunch Cruise

Shaterra_S, Aug 2025

Directions were poor but the cruise was very nice.

I can confirm that the instructions were awful. The pin that is in the reservation is for another parking lot. I recommend you follow the instructions that Viator gives you to start and then heed mine. The directions will take you to a parking lot on North Colombus Drive. If you stop there, you will miss your reservation. Make that right at the light on N Columbus Drive and go uphill. At the top of the hill, the NBC building should be on your right. If see a draw bridge, DO NOT CROSS IT. When you made it to the top of the hill, cross the street and make another right. You are standing at a parking lot again which is on your left now and facing ahead is the university of Chicago building. Right in front of the building there are some flags, that is where you will find stairs that will take you down to the Odyssey. Your destination will be immediately on your right. As for the cruise, the food was great. The portions were not small and the service was great. It was very informative, lively and a perfect time to spend the afternoon. Will return in the future for a dinner cruise.