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Private Sailing Cruises & Charters

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Multiple dates

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400 E Monroe St, Chicago, IL, USA

Starting at

$799

$699

 

outdoor activities

 

What you will experience

USE DISCOUNT CODE BUCKETLISTERS FOR $100 OFF YOUR CRUISE PRICE!

Bucket Listers is excited to partner with On A Boat Sailing to offer you exclusive ticket pricing:

💰Price list:
Playpen Boat Rental: Starting at $999 per boat with up to 6 passengers (originally $1,099)
Chicago Skyline Cruise: Starting at $799 per boat with up to 6 passengers (originally $899)
Navy Pier Fireworks Cruise: Starting at $699 per boat with up to 6 passengers (originally $799)
Wedding Party Cruise: Starting at $799 per boat with up to 6 passengers (originally $899)
Engagement Cruise: Starting at $599 per boat with up to 6 passengers (originally $699)
🗓️ Multiple dates and times
📍On A Boat Charter: 400 E. Monroe St., Chicago, IL 60601

About the event:

Chicago's top-rated sailing experience with over 500 five-star reviews. We're a one boat, one captain operation sharing our passion for sailing from Monroe Harbor in Downtown Chicago. Being a small outfit allows us to have attention to detail and curate the exact experience our guests are looking for. Our trips have been enjoyed by thousands of guests since our first private charter in 2017. Now in our 7th season, we pride ourselves on offering a safe & unforgettable way to get on Lake Michigan in the summer. Whether you're cruising the city skyline, partying hard at the playpen or taking in the Navy Pier fireworks from the best seats in the house - you won't forget the time you sailed Lake Michigan in luxury & style!


This event is all-ages
All sales are final. No refunds or exchanges.

 

What to consider

What's included?

✅ Coast Guard certified Captain
✅ Complimentary snacks and drinks
✅ Fridge with Ice
✅ Kitchenware including acrylic cups and stemware
✅ Pool floaties, life jackets and pool noodles

Are there extra costs?

We include in our booking price all fees and do not have any hidden costs. If you experience great service onboard, than a 10-20% tip for the captain is considered appropriate. Unlike other boats and companies we do not charge you extra for:

❌ Separate captain fee
❌ Fuel and docking
❌ Non-alcoholic drinks and snacks
❌ Damage/cleaning deposit

What food and drink can I bring on the boat?

You may bring any beverages of your choosing including beer, wine, champagne, or hard seltzers. No hard liquor on the boat please per our own safety precautions. Please do not bring red wine or other items that may stain the boat if spilled. We provide kitchenware and non-breakable acrylic glassware for our guests. We have a fridge with ice onboard to keep things cool.

Ahead of the cruise or while onboard guests may purchase our bottles of white wine, rose, champagne, packaged cases of beer or seltzers.

 

 

 

Where is the experience

400 E Monroe St, Chicago, IL, USA

 

Frequently asked questions

 

Starting at

$799

$699