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It's easy, and you can do everything online. No calls, no emails, no back-and-forth.
- Pick your boat, date, and time
- Pay securely and get instant confirmation
- Show up, step aboard, and go
Takes about two minutes.
Anchor just off Grant Park in calm water, with Navy Pier to the north and the full Chicago skyline behind you. Relaxed, beautiful, and effortlessly Chicago.
Monroe Harbor sits just off Grant Park: calm water, sweeping lakefront views, Navy Pier to the north, and the full Chicago skyline behind you. It’s the easiest and most scenic anchorage on the lake.
It offers something the Playpen doesn’t: quiet. The water here is calmer and more protected, the pace slower, and the view arguably more complete. You’re closer to the city’s architectural shoreline, with the lakefront running from Grant Park northward and Navy Pier lit up in the distance.
It’s the charter for groups who want to be on the water without the energy of the Playpen scene. Great for anniversaries, smaller corporate outings, photography, or any occasion where the vibe should be calm and beautiful rather than high-energy.
Monroe Harbor is the stretch of Lake Michigan off Grant Park, inside the breakwall between Navy Pier and the Museum Campus.
Burnham Harbor is the closest departure, a short cruise north along the lakefront. Travel time varies with conditions; your captain confirms the route and timing for your departure harbor.
Your captain gets you out to the harbor, finds a calm spot, and handles the anchor. From there it’s your afternoon: music on the boat’s Bluetooth system, drinks on deck, and the skyline close enough to pick out the buildings.
Sunset trips are particularly special: golden light on the Hancock and the Sears Tower, and the water holding the color longer than anything on land.
Monroe Harbor is also one of the best endings to a full day on the water. Start on the Chicago River, anchor at the Playpen for the afternoon, drift here for golden hour, and stay out for Navy Pier fireworks.
Starting vessel rates are not an all-inclusive total. Captain fees, packages, taxes, and other applicable charges depend on your booking.
Up to 13 guests37ft · Sea Ray
31st Street Harbor
Ask about swimming when booking
Up to 13 guests46ft · Sea Ray
31st Street Harbor
Ask about swimming when booking
Up to 13 guests48ft · Sea Ray
31st Street Harbor
Ask about swimming when booking
Up to 13 guests50ft · Sea Ray
31st Street Harbor
Ask about swimming when booking
Up to 13 guests52ft · Sea Ray
31st Street Harbor
Ask about swimming when booking
Up to 13 guests56ft · Sea Ray
31st Street Harbor
Ask about swimming when booking
Up to 49 guests57ft · Power Catamaran
River North Marina (600 W Chicago Ave)
Ask about swimming when booking
Up to 49 guests72ft · Chris Craft
Burnham Harbor
Cruising & socializing · no swimming
Up to 125 guests78ft · Power Catamaran
Burnham Harbor
Ask about swimming when booking
Vessel rates start at $285 per hour. Your total depends on the vessel, date, duration, captain arrangements, and any required packages or fees. Check live availability and your full booking total at checkout.
Check live pricing →Choose from vessels with capacities of 13 to 125 guests. Smaller groups are welcome, too. Your group must stay within the booked vessel’s passenger limit.
Browse the fleet →Monroe Harbor is calmer and more protected, with a slower pace and a closer view of the lakefront from Grant Park north to Navy Pier. The Playpen is the livelier scene, with more boats and more music.
Explore the Playpen →Sunset. Golden light on the skyline is the reason most groups come. Our charter season is March–October; weather and vessel availability determine individual departures.
Charters start at a three-hour minimum, and most Monroe Harbor groups book 3–4 hours. It also works as the last stop on a full-day charter that starts on the Chicago River.
Burnham Harbor is the closest departure. Charters also leave from 31st Street Harbor, Burnham Harbor, and River North Marina (600 W Chicago Ave), depending on your vessel. Use the departure address in your booking confirmation.
Departure information →On 13-passenger boats, bring your own food and drinks. Larger vessels offer drinks packages and catering; outside-beverage and food policies vary by vessel. Check the vessel details before packing.
Explore catering →Our 13-passenger bareboat charters require guests to hire a separately licensed captain (after checkout, you review our vetted list and pay your captain directly), while all larger yachts include a licensed captain and crew.
It's easy, and you can do everything online. No calls, no emails, no back-and-forth.
Takes about two minutes.
Want catering, or a pickup or drop-off somewhere other than our dock? Reach out and we'll plan as much of your day as you like.