What is the minimum age to attend?

This event is 21+; bring government-issued photo ID to verify age at check-in.

How long is the cruise?

The listed duration is approximately two hours.

Where do I board the fireboat?

A specific meeting point is not provided here; check the operator’s booking page for exact boarding location and check-in times.

Is the event wheelchair accessible?

No information about accessibility is provided in the listing; contact the operator directly via the booking portal for details and accommodations.

Can I bring food or drinks?

Details about food and beverage service are not specified; check the booking page for current on-board policies and available options.

What happens if the weather is bad?

Weather-related cancellations or changes are handled by the operator; review the booking terms or contact them for the most current policy.

Chicago Fireboat Comedy Cruise with Joshua Black — Skyline Stand-Up on the Water

Josh Black's Comedy Cruise runs for two hours aboard Chicago’s historic fireboat, launching from the river near downtown Chicago. The experience pairs stand-up sets with panoramic views of the skyline along the Chicago River and Lake Michigan. Created and hosted by Joshua Black, a touring stand-up comedian and former firefighter with over 500,000 TikTok followers, the show trades traditional comedy club walls for the low hum of engines and the occasional river tug.

Boarding feels like stepping into a piece of civic history: the vessel is one of the city’s most historic fireboats, its steel decks and brass fittings hinting at an era when it fought blazes along the lakeshore. Against that industrial backdrop, rotating touring comedians deliver tight, contemporary sets while the city’s architectural profile slides by—Wrigley Building facades, glass towers, and the bridges that lift and lower over the river. The route takes you past the river’s key features and out onto the open water for skyline views framed by the sweep of Lake Michigan.

This event is compact—about two hours—so it’s accessible for evening schedules and makes a memorable addition to any Chicago visit. It is 21+ only, and language and material are geared toward an adult audience. The production benefits from Joshua Black’s background: the show’s origin story comes from a fireman’s perspective, and that authenticity gives the evening a playful, slightly irreverent edge. Expect professional stand-up pacing, mic work, and a lineup that rotates to keep repeat nights fresh.

Practical notes: bring a jacket even on summer evenings—the lake breeze can cut through layers. Seating is stable but slightly exposed, so wear flat shoes and secure loose items. There is no information provided about wheelchair accessibility or group size; check the operator’s booking page for specifics. Photography is encouraged: skyline shots at sunset are the most cinematic, while candid shots of comedians on deck capture the rare juxtaposition of performance and maritime heritage.

As a local offering, this cruise stands out because it transforms a historic municipal vessel into a cultural venue. It shines a light—literally and figuratively—on Chicago’s relationship to water, architecture, and public service history. For visitors seeking something that merges nightlife with place-based storytelling and excellent views, Josh Black’s Comedy Cruise is an inventive, laugh-forward way to experience the city from the river.

About Chicago Fireboat Tours

Chicago Fireboat Tours operates a fleet of public cruises and special-event voyages from Chicago's lakefront, offering scenic views, historical interpretation, and unique hospitality on a retired fireboat. The flagship vessel, the Fred A. Busse (Engine 41), served Chicago from 1937 to 1981 and is preserved as a floating museum with firefighting artifacts, memorabilia, and firefighter patches that document its history.

Departures leave from 111 N Lake Shore Drive and include a range of curated experiences: a Fireworks Cruise timed with Navy Pier displays, a Sunset Cruise, Historical and Architectural Lake & River Tours guided by expert docents, OktoberFest and Brew Cruises with local breweries, Pizza Cruises in collaboration with Chicago Pizza Tours, Venetian Night events, and special Air Show Cruises. Trip lengths vary from approximately 90 minutes to 3.5 hours depending on the itinerary.

Tours combine guided interpretation of Chicago fire history and architecture with skyline and riverfront sightseeing, delivering both education and entertainment for families, groups, and visitors. Live music, curated menus, and on-board beverages feature on select departures to enhance the experience. Reservations and schedules are offered seasonally, with specific event cruises timed to city festivals and the annual Chicago Air & Water Show.

Chicago Fireboat Tours emphasizes historical authenticity, public safety, and memorable on-water access to Chicago’s skyline. The combination of a historic vessel, docent-led stories, and curated event cruises make it a distinctive option for visitors seeking an alternative lakefront experience. Ticketing information, accessibility details, and seasonal schedules are regularly published on the tour operator's website.