Focus on the View, Not the Bill

Private, captain-led luxury charters for up to 6 guests, departing directly from Chicago’s iconic Navy Pier Marina.

Unlike many charters that tack on surcharges after the fact, Bayside Voyage offers fully transparent pricing from the moment you book.

All-Inclusive Pricing:

(Enjoy the cruise and forget the sticker shock)

Included:

  • A USCG-licensed captain (*No separate Captain Fee*)

  • All fuel and gas costs for your cruise on Lake Michigan

  • Taxes like Illinois ROT (around 10.25% in Chicago)

  • Ice, Coolers, Huge Lily Pad, Towels, & Complimentary Bottled Water (BYOB)

*Gratuity not included but always appreciated*

Chicago’s Front-Row Seat

Every trip is different, and yours can be too. Choose one of our signature experiences below, or tell us exactly how you want to spend your time on the water.

Signature Experiences

  • Navy Pier Fireworks Cruise

  • Sunset Skyline Cruise

  • The Playpen Experience

  • Chicago River Cruise

  • Special Events & Small Corporate Outings

What You'll See

  • The Skyline — Sweeping, panoramic views of the entire Chicago lakefront.

  • The Chicago River — It's a totally different city from the water, and honestly one of the coolest ways to experience Chicago.

  • The Museum Campus — Get up close to the Shedd Aquarium, Adler Planetarium, and Buckingham Fountain.

  • Stadiums & Stages — Cruise past Soldier Field and the Huntington Bank Pavilion at Northerly Island.

  • The Playpen & Ohio Street Beach — Drop anchor and join the energy of Chicago's premier lakefront social scene.

We're available 7 days a week and happy to accommodate special time requests.

Visit the Playpen, Swim, sunset cruise around Chicago, Cruise Chicago River, Watch Navy Pier Fireworks

Weekend Charters (Fri & Sun)

Chicago's weekends on the water — when the skyline, the lake, and the energy of the city all come together. Whether you're planning a daytime cruise or watching the sun set over Lake Michigan, weekend charters are our most popular booking window.

Chicago River Cruise — Wind through the heart of downtown for an up-close look at the city's famous architecture, bridges, and skyline from a completely different angle.

Sunset Cruise — Head out onto Lake Michigan as the sky turns gold and pink over the water, with the Chicago skyline glowing behind you. A favorite for date nights and special occasions.

The Playpen — Anchor with us in the legendary Playpen, Chicago's iconic on-water gathering spot just off Oak Street Beach, where the lake comes alive with boats, music, and summer energy.

Departure Times

Daytime Charters: 11am, 12pm, 1pm, 2pm
Evening Charters: 3pm, 4pm, 5pm, 6pm

(2, 3 or 4 Hour Charters)

Weekend Pricing (Saturday & Sunday)

2 Hour Charter — $900

3 Hour Charter — $1200

4 Hour Charter — $1400

Included:

A USCG-licensed captain - All fuel and gas costs for your cruise on Lake Michigan - Taxes like Illinois ROT (around 10.25% in Chicago) Gratuity not included but always appreciated.

Week Day Charter (Mon-Thurs)

Beat the weekend crowds and enjoy Lake Michigan and the Chicago River at their calmest. Bayside Voyage's weekday charters (Monday–Thursday) give you the same private, captain-led experience — just with more flexibility on timing and a quieter city backdrop. Choose the voyage that fits your day:

Chicago River Cruise — Wind through the heart of downtown for an up-close look at the city's famous architecture, bridges, and skyline from a completely different angle.

Sunset Cruise — Head out onto Lake Michigan as the sky turns gold and pink over the water, with the Chicago skyline glowing behind you. A favorite for date nights and special occasions.

The Playpen — Anchor with us in the legendary Playpen, Chicago's iconic on-water gathering spot just off Oak Street Beach, where the lake comes alive with boats, music, and summer energy.

Departure Times

Daytime Charters: 11am, 12pm, 1pm, 2pm
Evening Charters: 3pm, 4pm, 5pm, 6pm

(2, 3, or 4 Hour Charters)

Weekday Pricing (Monday thru Thursday)

2 Hour Charter — $800

3 Hour Charter — $1050

4 Hour Charter — $1200

Included:

A USCG-licensed captain - All fuel and gas costs for your cruise on Lake Michigan - Taxes like Illinois ROT (around 10.25% in Chicago) Gratuity not included but always appreciated.

Fireworks Cruise (Wed & Sat)

There's no better seat for Chicago's summer fireworks than the deck of your own private charter. Every Wednesday and Saturday night, Navy Pier lights up the sky over Lake Michigan — and Bayside Voyage puts you right on the water to watch it unfold, away from the crowds on the pier and with an unobstructed view of the skyline glowing behind the show.

Wednesday cruises depart at 8:30 PM and run until 10:30 PM, while Saturday cruises run from 9 PM to 11 PM, timed perfectly to catch the show from open water. It's one of our most requested experiences — a favorite for date nights, birthdays, and anyone who wants to see Chicago's fireworks the way they're meant to be seen.

Departure Times

Wednesday: 8pm to 10pm
Saturday: 8:30pm to 10:30pm

(3 or 4 Hour Charters)

Fireworks Pricing

Wednesday or Saturday: $800 for 2 hrs

Included:

A USCG-licensed captain - All fuel and gas costs for your cruise on Lake Michigan - Taxes like Illinois ROT (around 10.25% in Chicago) Gratuity not included but always appreciated.

View of a luxurious yacht docked at a marina during sunset with a cityscape, including a Ferris wheel and tall buildings, in the background. The yacht's deck has a table with drinks, a bouquet of flowers, and seating.
Interior view of a boat showing white cushioned seating with headrests, a small table, and the view through an opening to the dock with boats and water outside.
A white yacht docked at a marina with calm water, behind a concrete wall and a black fence, under a partly cloudy sky.
Interior of a boat with a cream-colored leather sofa, wooden cabinets, a small dining area, a bed, and a window.
Interior of a boat or RV with cream-colored leather seating, a small table, a wall-mounted TV, and wooden cabinets.
Close-up view of a yacht's interior showing a flat-screen monitor, speakers, and part of the boat's ceiling with window and city skyline in the background.
The image shows the interior of a boat, including white cushioned seats, a small wooden table, a built-in grill, and various equipment and storage compartments.
View from a boat showing a white cushioned seat with the embroidered words 'Sea Ray,' a set of black gift bags with 'Bayside Voyages Chicago, IL' logo hanging on the seat, and a marina with parked boats and a brick building in the background.

Boat Amenities

Two women in a yellow and blue pedal boat on the water with a city skyline in the background.

  • Premium Sound & Connectivity: Integrated Bluetooth audio system to set the mood with your own playlists.

  • Refreshments & Comfort: Complimentary bottled water and ice provided; guests are welcome to BYOB and bring snacks.

  • Private Facilities: Access to a clean, well-maintained onboard head (restroom) for your comfort throughout the trip.

  • Safety First: Fully equipped with professional-grade safety gear and commercial insurance for total peace of mind.

  • Swimming Access: Integrated swim platform and boarding ladder for those mid-lake dips.

  • Giant Lily Pad: Free to use and can fit 11 adults

  • Tableware: Plastic utensils, plates, napkins,

Four women sitting and posing on a boat with a city skyline, water, and other boats in the background during sunset.
View from the boat showing three women on a boat deck, one drinking from a cup, two facing away, with a city skyline in the distance and a blue sky with clouds.
People on a boat watching fireworks display in the evening sky.
A group of five men standing closely together on a city rooftop with tall buildings in the background, smiling and enjoying each other's company in casual summer clothes and sunglasses.
A group of six friends sitting on a boat with a city skyline and a bridge in the background, enjoying drinks and smiling at the camera during daytime.
People sitting on a boat watching fireworks light up the night sky over a city skyline with tall buildings.
People standing on a boat in a city with tall buildings and skyscrapers along the water, with some boats visible in the water.
Group of five women enjoying a boat ride on the water in an urban area with skyscrapers and yachts in the background. They are smiling, wearing sunglasses and swimsuits, and holding drinks.
People relaxing on a boat, sitting on the deck, with a city skyline in the background and a clear blue sky.
Group of people on a boat holding small cups, with a body of water, a boat, and a distant shoreline in the background.
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A 6-Pack Charter.

It might seem like more guests means more value — but on the water, it's the opposite. Many bareboat charters pack in up to 13 passengers to maximize revenue per trip, leaving you crowded, competing for space, and carrying more liability and risk.

Bayside Voyage is permitted up to 6 guests per maritime law. This is by design and by choice.

That means:

  • Room to actually move. Stretch out, swim, relax, and enjoy the space and "white glove" service we strive for with up to 6 of your closest family and friends (bring the dog too, if you want).

  • A captain who knows the boat — not a rental agreement you're responsible for. With bareboat charters carrying up to 13 passengers, more people usually means more liability resting on the renter, not less.

  • An experience built around your group, not maximum headcount. Fewer guests means more attention, more flexibility, and a trip that feels private instead of packed.

Inquiries: