The Best Boat Rentals in Chicago

Expect most private charters to run about $200–$350 per hour for mid-size powerboats, $300–$800 per hour for larger yachts, and $600–$900 per hour for inspected party boats that carry 14–24 guests. Smaller self-operated boats on the Chicago River often start around $150–$200 per hour. Prices vary by date, boat size, and event times (holidays and fireworks nights usually cost more). Most rentals include U.S. Coast Guard–approved safety gear, a Bluetooth sound system, and basic amenities like coolers; many also include ice and a floating mat. Plan for captain’s fees ($100–$150 per hour on many listings), fuel or a flat fuel surcharge, taxes, and customary 15–20% gratuity when service is excellent.

You’ll find a wide mix: comfortable motor yachts and cabin cruisers for 6–12 guests, inspected party boats for larger groups, sporty bowriders and deck boats, spacious pontoons perfect for relaxing in the Playpen, classic sailboats for skyline cruising, and fishing charters on Lake Michigan. Availability changes throughout the season, but there’s usually a good selection for everything from low-key sightseeing to big celebrations.

In Illinois, anyone born on or after January 1, 1998 must hold a state-accepted boating safety certificate to operate a motorboat over 10 horsepower. Many Chicago listings either include a licensed captain or require you to hire one, especially for Lake Michigan trips. Self-operated options are more common on the Chicago River with easy-to-handle boats; always review the listing’s rules and experience requirements before booking.

The most common pickup points are the downtown harbors along the lakefront. Popular locations include DuSable Harbor near Randolph Street/Navy Pier, Burnham Harbor by the Museum Campus, Monroe Harbor’s moorings just off Grant Park, and 31st Street Harbor to the south. You’ll also see departures from Diversey and Belmont Harbors on the North Side. Your captain will confirm the exact dock and any parking guidance; rideshare drop-offs are often the easiest option on busy weekends.

On the lake, you’ll cruise past the full skyline, Navy Pier, and the Museum Campus with the Adler Planetarium, Shedd Aquarium, and Field Museum front and center. A popular stop is the Playpen, a calm anchorage just north of Navy Pier for swimming and floating on nice days. If you head onto the Chicago River, you’ll pass through the Chicago Harbor Lock and then glide by architectural icons such as the Wrigley Building, Tribune Tower, Marina City, and the Merchandise Mart with great photo angles you can’t get from land.

Yes—families are welcome and children count toward the boat’s maximum capacity. Every charter provides Coast Guard–approved life jackets in a range of sizes, and many operators require kids to wear them while underway. If you need infant or toddler sizes, ask your captain in advance so they’re set aside before boarding. Strollers are usually best left on the dock; bring soft-soled shoes and sun protection for little ones.

Most private charters are BYOB and allow snacks or catered platters. Glass cups are typically not allowed; bring cans or plastic drinkware, and keep any wine or champagne bottles secured. Many boats include coolers and ice; some have a fridge. Red wine, messy sauces, and hard-to-clean foods are often discouraged to protect upholstery. Open-flame grilling is rarely permitted—ask your captain about approved warming or serving options.

Pet policies vary by vessel. Many yachts do not allow animals for safety and cleaning reasons, while a few captains may approve a small, well-behaved dog with advance notice and a deposit. If bringing a pet is essential, filter for pet-friendly listings and confirm rules about leashes, life jackets for dogs, and where pets can sit during the cruise.

Captains watch the marine forecast closely. Light rain or passing showers rarely cancel a trip, but conditions like high winds, rough waves, lightning, or small craft advisories can delay or postpone. If your captain deems it unsafe to depart, you’ll typically be offered a reschedule or weather credit per the listing’s policy. Summer storms can pop up fast on Lake Michigan, so keep your phone handy for day-of updates and arrive a few minutes early in case the window to depart is tight.

Absolutely. Chicago’s boating scene is built for celebrations—think skyline sunsets, swimming at the Playpen, or timing a cruise with Navy Pier’s summer fireworks. Many boats include a floating mat, Bluetooth speakers, and space to serve snacks. For big weekends (Memorial Day, July 4th timeframe, Labor Day, and the Chicago Air & Water Show), book well in advance and lock your guest count early so the captain can recommend the right vessel and time slot.

Peak season runs May through September, with the harbor season typically operating from May 1 to October 31. Major boating holidays include Memorial Day weekend, the July 4th period, and Labor Day. The Chicago Air & Water Show is a highlight in mid-August and sells out early. Summer fireworks from Navy Pier are scheduled on Wednesday and Saturday nights, making those evenings especially popular. For calmer water and easier parking, try weekday mornings; afternoons and weekends are livelier but busier.

Most groups pick a captained charter for stress-free fun and local know-how, especially on Lake Michigan where wind and wave conditions can change quickly. If your goal is to relax, toast a special occasion, or time a cruise with fireworks, a captain is the way to go. Self-operated rentals are best for confident boaters, often on the river with easy-handling boats; you’ll need to meet age, certification, and experience requirements and follow all local rules.

The Playpen is a popular, breakwater-protected cove just north of Navy Pier, roughly off Oak Street and Ohio Street Beaches. On warm, calm days, boats anchor to swim and float with a backdrop of the skyline; on choppier or windy days, your captain may choose a different plan for comfort and safety. Capacity limits, raft-up etiquette, and respectful noise levels all apply—follow your captain’s instructions and pack easy, no-glass drinks for a smooth stop.