Top Chicago Cruises &amp; Sailing - page 2

Small-Group Sightseeing Boat Tour in Chicago

1 hour 30 minutesFree Cancellation

5.0

(97)

from $89

Enjoy an unforgettable evening on Lake Michigan with the Chicago Fireworks Cruise. Witness the stunning skyline as you glide across the water, leading up to the spectacular fireworks display at Navy Pier. This 1.5-hour cruise offers a unique perspective of the city while providing a relaxed atmosphere for friends and family to gather and enjoy the show. Boarding begins 15 minutes prior to departure, so arrive early to secure your spot and make the most of this dazzling experience. - 1.5-hour cruise featuring panoramic views of Chicago's skyline - Marvel at the iconic fireworks show off Navy Pier - Departing and returning to 111 N Lake Shore Drive

Chicago Fireboat Fireworks Cruise

1 hour 30 minutesFree Cancellation

4.9

(8)

from $57

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

30 minutesFree Cancellation

4.1

(346)

from $36

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

Enjoy waterfront views of downtown Chicago on a 2-hour brunch cruise through the heart of the city. Board a luxurious yacht at Navy Pier then relax on deck with a complementary mimosa. Find a comfortable spot on the three climate-controlled observation decks, and enjoy a sumptuous buffet while the onboard DJ spins a leisurely afternoon playlist. Capture unforgettable images of downtown skyscrapers and architectural landmarks as you navigate along the historic shoreline, then loop back and finish your outing at the bustling Navy Pier.

City Cruises Chicago: Premier Lake Michigan Brunch Cruise

2 hoursFree Cancellation

3.9

(28)

from $105

Monday Night Concert Series: Blues and Views Aboard Tall Ship

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

2 hours

5.0

(1)

from $81

Chicago's Fireworks Show aboard Tall Ship Windy!

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!

1 hour 30 minutes

4.6

(17)

from $114

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

Likely to Sell Out

City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

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

2 to 3 hoursFree Cancellation

4.0

(6)

from $169

Likely to Sell Out

Navy Pier Fireworks Cruise On A Private Sailing Yacht

from $1,099

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.

The Chicago River, as seen from our stop on wacky Wacker Drive

Chicago City Tour with Architecture River Cruise Option

2 to 4 hoursFree Cancellation

4.8

(727)

from $50

Navy Pier Chicago: Private Sailboat Charter with Captain

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

from $1,099

Chicago City Private Tours

2 to 8 hoursFree Cancellation

4.7

(31)

from $199

Enjoy a serene evening on Lake Michigan with a private sunset sailing charter, where the stunning Chicago skyline transforms as the sun sets. Departing from Montrose Harbor, this exclusive experience offers a cozy atmosphere for date nights, anniversaries, and memorable celebrations. Aboard the Vagabond, a Beneteau Oceanis 393 yacht, guests can unwind, capture picturesque moments, and savor their favorite BYOB drinks and snacks against the backdrop of golden-hour light. With a dedicated captain overseeing your journey, relish a tranquil escape just minutes from the bustling city.

Private Chicago Sunset Sailing Charter on Lake Michigan

Private Chicago Sunset Sailing Charter on Lake Michigan

4.5

from $1,350

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

Chicago City Tours See It All No Time Wasted

4 to 8 hoursFree Cancellation

3.8

(21)

from $150

Likely to Sell Out

Chicago River Tiki Bar Party Cruise from Chicago Riverwalk

1 hour 15 minutes

4.0

(118)

from $42

Private Lake Michigan Sailing Charter with Skyline Views

A private sailing charter on Lake Michigan offers a serene escape with stunning skyline views of Chicago. Departing from Montrose Harbor, enjoy a relaxed atmosphere ideal for families, couples, or casual groups looking for a break from city life. Experience the charm of a personal sailing trip as you glide across the water, capturing perfect moments of the skyline from your private vessel. This charter caters to visitors and locals alike, providing a unique perspective of the city while ensuring a peaceful outing on the lake. - Private sailboat reserved exclusively for your group - BYOB-friendly with restroom and cooler space onboard - Scenic views of the Chicago skyline and lakefront - Ideal for families, groups, couples, and first-time sailors

Private Lake Michigan Sailing Charter with Skyline Views

4.5

from $1,150

Don’t miss Chicago’s famous sights and fabulous views on this award-winning private sightseeing tour of the city. Travel through Chicago with an expert guide on a comfortable minibus, stopping at iconic locations like early skyscraper "The Rookery" (Frank Lloyd Wright architecture), Museum Campus (for the BEST skyline view in town), Millennium Park (The Bean), Buckingham Fountain, The Magnificent Mile, Lincoln Park, Chicago River, The Gold Coast, Lake Shore Drive and more! Along the way, your guide will provide historical and informational commentary about the area and its beautiful attractions. Your private tour ensures a more personal experience. If you would like to take the tour at a time other than what is offered, please note in special requests field when booking. The best way to tour at this time! Sanitized vehicles with just your group.

Private Chicago City Minibus Tour

2 hoursFree Cancellation

5.0

(1)

from $379

Discover the very best of New York City in one unforgettable experience! From the majestic Statue of Liberty and the historic Brooklyn Bridge to famous neighborhoods, hidden gems, and picture-perfect skyline views — this tour captures it all. Enjoy guided stops at iconic landmarks, learn fascinating stories from your local guide, and experience the true energy of the city that never sleeps. Perfect for first-time visitors or anyone wanting to see it all, this experience blends history, culture, and unbeatable photo ops at every turn. Come ready to explore, snap amazing pictures, and make lasting memories on the ultimate NYC adventure!

2 to 7 hoursFree Cancellation

Chicago VIP Private Tour

4.5

from $499

Enjoy a fun, festive, and one-of-a-kind way to admire the Chicago skyline and views over Lake Michigan aboard this tiki boat tour. Choose from several start times, meet your tiki-themed vessel right on the Chicago Riverwalk, and climb aboard. As you sail along the Chicago River and out onto Lake Michigan, you’ll enjoy a new perspective on the Windy City—and can purchase mimosas and other beverages at the on-board cash bar.

Chicago Lake Michigan Skyline Sunday Funday Party Cruise

Chicago Lake Michigan Skyline Sunday Funday Party Cruise

1 minute to 1 hour 30 minutes

4.2

(6)

from $42

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 $56

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

One-Way Private Airport Transfer by Sedan

30 to 45 minutesFree Cancellation

4.0

(4)

from $179

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What are people saying about Chicago

Chicago CityPASS®

Paul_M, Jun 2026

Save some cash with the CityPass

City Pass is a great way to see Chicago if you know you are going to some of the most popular museums (Field and Shedd) and then allow for some other excursions that you wouldn’t necessarily want to pay full price for (Skydeck, Architecture Cruise) but were still enjoyable and save some cash overall. The Adler Planetarium was a nice find. I would not use for the art institute if you have kids under 13 as they get in for free.

Chicago By Night River and Lake Cruise

Agnes_G, Jun 2026

This was one of the best...

This was one of the best boat tours we experienced. The tour was well organized, the boat was well maintained. Chicago is a beautiful city, the night view was spectacular. Olivia did an excellent job presenting the highlights and history of the buildings. We particularly appreciate her presentation of the architectural backgrounds of the shoreline buildings. If you only have time to take one boat tour in the city I would highly recommend this one.

Lake Michigan Sunset Cruise in Chicago

Jeanette_T, Jun 2026

Amazing trip.

There are no signs for this meeting location. What you should see is a group of people standing near some stairs, look for a small podium, and the name of the company who runs the tours is Welldom I believe. The tour was great, the guide was entertaining and informative, but just being on the lake. Seeing that beautiful city from the night view. This is even a good trip.If you have difficulty walking as I do, ask for assistance. There is an elevator that goes down to the lower level. This is an event everyone can enjoy.

Chicago Sightseeing River and Lake Cruise

Larry_E, Jun 2026

Chicago River/Lake Michigan skyline tour

Fantastic boat tour of the Chicago River and Lake Michigan! The views of the skyline were breathtaking, and the guide provided interesting history and architectural insights throughout the trip. Seeing Chicago from the water offered a unique perspective, especially when transitioning from the river to the lake. The boat was comfortable, the crew was friendly, and the experience was well worth it!

Historical and Architectural Chicago Fireboat River & Lake Cruise

Karl_D, Jun 2026

Great trip the weather didn’t cooperate with.

Unfortunately, it was too windy for the Fireboat to navigate the waters. The staff on the boat were very pleasant and disappointed that we couldn’t leave the dock. We were refunded the entire cost. We are hopeful that we can return the summer to experience the tour.

Chicago Architectural River Cruise

Amy_P, Jun 2026

Worth it, honestly.

This boat tour was excellent (and I’ve done a couple in Chicago) staff was pleasant, free soft drinks and lemonade, seating was good. We came very close to leaving time and sat on the side of the boat and was still great. Our tour guide Lynn was extremely knowledgeable and her voice was very pleasant. I would 100% do it again.

City Cruises Chicago: Premier Plus Brunch Cruise on Chicago River

Fatmata_B, May 2026

The Trip was great. Good...

The Trip was great. Good ambience, Trish was exceptional she made us feel welcome and very comfortable. The food was great and the scenery is spectacular if you need to take pictures. The Dj on board was great he played good music and also his tour guide was great. This trip is definitely worth it.

Small-Group Sightseeing Boat Tour in Chicago

Sian_S, Sep 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.

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.