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Chicago Playpen
Boat Rental
Take your boat rental to the Chicago Playpen, drop anchor off the skyline, and spend the day swimming, playing music, and hanging out on Lake Michigan.
Drop Anchor – Stay A While 41°54′ N 87°36′ W
- 4.9★from 1,071+ reviews
- 175,000+guests on the water
- 12,000+charters
- 23 vesselsUp to 13, 49 & 125 guests
What Is the
Chicago Playpen?
The Chicago Playpen is one of the city’s most popular places to spend a summer day on the water. Located on Lake Michigan between Navy Pier and Oak Street Beach, it’s a protected anchorage where boaters come to drop anchor, swim, listen to music, and hang out with one of the best views of the Chicago skyline.
The Playpen isn’t a beach or a sandbar you can walk out to. It’s a boating area, and you need a boat to get there. The breakwalls around Chicago Harbor help keep the water calmer than the open lake, making it a natural gathering spot for boaters.
On warm weekends, especially from June through September, the area fills up quickly. You’ll see everything from smaller boats to large yachts anchored nearby, with people swimming, having drinks, relaxing on deck, and spending the afternoon on the lake having a great time.
If you’re renting a boat to visit the Playpen, your trip starts at the harbor. From there, it’s a short cruise out to the anchorage and the Chicago skyline.
Where Is the Playpen?
The Playpen sits on Lake Michigan roughly between Navy Pier and Oak Street Beach, inside the breakwall off the Gold Coast shoreline.
From 31st Street Harbor, the cruise takes around 35 minutes, heading north along the lakefront with the Chicago skyline beside you. Travel time varies with conditions; your captain confirms the route and timing for your departure harbor.
What a Playpen
Day Looks Like
Your captain will get you out to the Playpen, find a good spot, and handle the anchor. Once you’re settled in, you can hang out on the bow, put your own music on through the boat’s Bluetooth system, and enjoy the afternoon. On boats that allow swimming, you can hop in once your captain lets you know it’s safe.
July and August weekends are when the Playpen is at its busiest, with more boats, more music, and a much livelier atmosphere. If you want the same skyline and experience without as much boat traffic, weekdays are usually a better choice.
Looking for something a little quieter? Monroe Harbor is another great place to anchor and spend some time on the water.
The Details
- Starting rate
- From $285/hour Check live pricing →
- Season
- March–OctoberSubject to weather and availability
- Your group
- Vessels for up to 13 guests 49 guests 125 guests
- Departure harbors
- 31st Street Harbor, Burnham Harbor, and River North Marina (600 W Chicago Ave)
- Captain
- 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.
- Food & drink
- 13-passenger boats: bring your own. Larger vessels: drinks packages and catering options.
Starting vessel rates are not an all-inclusive total. Captain fees, packages, taxes, and other applicable charges depend on your booking.
Boats for the Playpen
Up to 13 guests37ft · Sea Ray
Sundancer
31st Street Harbor
Ask about swimming when booking
From $285 / hour
Up to 13 guests46ft · Sea Ray
Express
31st Street Harbor
Ask about swimming when booking
From $310 / hour
Up to 13 guests48ft · Sea Ray
Sundancer
31st Street Harbor
Ask about swimming when booking
From $335 / hour
Up to 13 guests50ft · Sea Ray
Sundancer
31st Street Harbor
Ask about swimming when booking
From $350 / hour
Up to 13 guests52ft · Sea Ray
Sundancer
31st Street Harbor
Ask about swimming when booking
From $395 / hour
Up to 13 guests56ft · Sea Ray
Sundancer
31st Street Harbor
Ask about swimming when booking
From $420 / hour
Up to 49 guests57ft · Power Catamaran
Montauk
River North Marina (600 W Chicago Ave)
Ask about swimming when booking
From $1,000 / hour
Up to 49 guests72ft · Chris Craft
Sophisticated Lady
Burnham Harbor
Cruising & socializing · no swimming
From $1,350 / hour
Up to 125 guests78ft · Power Catamaran
Amalfi
Burnham Harbor
Ask about swimming when booking
From $1,600 / hour
From our Google reviews
Guests on Their
Playpen Day
★★★★★
“We had the most fun nighttime trip to the playpen. The booking process was smooth, quick, and easy.”
★★★★★
“KMB made chartering a yacht such an easy experience and we loved our day at the playpen with Captain Marty.”
★★★★★
“We booked for 4 hours and I am so happy we did, because it takes 30+ minutes to get to and from the playpen…”
★★★★★
“Cruising along Lake Michigan and being in the Playpen provided breathtaking views of the city’s landmarks.”
★★★★★
“This is the safest way to book a boat on the playpen for a guaranteed LITuation! Run…don’t walk to book!”
★★★★★
“…our captain drove us up and down the lake for a scenic boat ride before we docked in the playpen.”
How much does it cost to rent a boat to the Chicago Playpen?
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 →How many people can go on a Chicago Playpen boat rental?
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 →Can I bring my own food and drinks?
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 →Is a captain included?
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.
When is the best time to visit the Chicago Playpen?
July and August weekends bring the biggest scene. Weekdays offer the same skyline with less traffic. Our charter season is March–October; weather and vessel availability determine individual departures.
Where do Chicago Playpen charters depart from?
Departures are 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. The cruise from 31st Street Harbor to the Playpen takes around 35 minutes, depending on conditions. Your captain can confirm timing from other departure harbors.
Departure information →How deep is the Playpen in Chicago?
The Chicago Playpen averages about 12–18 feet deep. Depth varies across the anchorage and with lake levels. Ask your captain about the depth at your chosen anchoring spot before entering the water. Do not assume you can stand on the bottom or dive safely.
Can you swim at the Playpen?
Yes, on vessels that permit swimming and when your captain confirms conditions are suitable. Amalfi and Montauk list swimming among their included activities. Confirm swimming access for your chosen boat before booking, and follow your captain’s life-jacket and water-entry instructions.
Why is it called the Playpen?
The boating nickname refers to the sheltered pocket of water inside the breakwall, where boats gather to anchor and socialize with the skyline behind them.
Can we tie up to other boats at the Playpen?
No. Tying boats together can push a group past the 13-passenger limit set by U.S. Coast Guard bareboat charter regulations and voids our insurance coverage. For a bigger group, book a larger passenger charter or multiple boats anchored at least 75 feet apart. Guests can swim or float between boats but cannot board another chartered vessel.
Do I need a boating license?
You do not need to operate the boat yourself; a licensed captain handles navigation and anchoring. 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.
Add to your day at The Playpen
Book your Playpen boat rental, or plan the day with us.
Let us plan it with you.
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.
- Catering Food and drinks waiting on board
- Custom pickup & drop-off River docks, restaurants, anywhere off our route
- Full-day planning We map the whole day, start to finish