Charter a Boat from a Chicago Harbor
Pick the harbor closest to you — or pick the trip type, and we'll match you with the right boat and a USCG-licensed captain.
Departing harbors
Each Chicago harbor has its own character. Pick the one closest to where you're staying — or to where you want to be on the water.
Burnham Harbor
Chicago's downtown harbor — minutes from the Loop, anchored by Soldier Field and the museum campus.
Charter from Burnham Harbor →
Monroe Harbor
Chicago's largest harbor — the working heart of the city's charter fleet, between Grant Park and the lakefront events that define summer.
Charter from Monroe Harbor →
Diversey Harbor
Lincoln Park's harbor — a tree-lined North Side launch with the city's best southward skyline view.
Charter from Diversey Harbor →
Belmont Harbor
Lakeview's harbor — a working harbor close to Wrigley Field, Belmont Yacht Club, and the heart of the North Side neighborhood scene.
Charter from Belmont Harbor →
Jackson Park Harbor
Chicago's South Side gateway harbor — Hyde Park, the Museum of Science and Industry, and the future Obama Presidential Center.
Charter from Jackson Park Harbor →
31st Street Harbor
Chicago's newest harbor — modern facilities, easy lakefront-trail access, and the closest harbor to Bronzeville, Pilsen, and Chinatown.
Charter from 31st Street Harbor →
Calumet River & South Side Waterways
Chicago's overlooked South Side waterway — the captain's-perspective routes the paddler blogs miss.
Charter from Calumet River & South Side Waterways →
Hammond Marina
Indiana's gateway to Lake Michigan dive sites and deep-water fishing — direct access to the lake's biggest wrecks and salmon trolling lanes.
Charter from Hammond Marina →
Trip types
Already know what you want? Jump straight to the charter type.
Scenic Cruises
$200–$600
Chicago's skyline from the best seat in the house — on the water.
Dive Charters
$400–$800
Explore Lake Michigan's hidden world — shipwrecks, reefs, and more.
Corporate Events
$800–$3,000
Team building, client entertainment, and celebrations on the water.
Fishing Charters
$400–$1,000
Salmon, trout, and perch — Lake Michigan's best fishing, guided.
Sailing Instruction
$200–$500
Learn to sail on Lake Michigan with ASA-certified instructors.
Fireworks Cruises
$300–$700
The best seat for Navy Pier fireworks is on the water.
Playpen Cruises
$300–$800
Chicago's floating party — the Playpen sandbar experience.
River Cruises
$250–$600
Cruise the Chicago River — architecture, history, and hidden gems.
Or browse the fleet
See every boat available right now, with photos, capacity, and captain info — pick the one that fits your day.
Browse all boats