Water-Activities: Skyline Sunset Cruise in Chicago
Difficulty
easy
Duration
2.5 hours
Fitness Level
Minimal physical activity required, suitable for most guests
Overview
Discover Chicago’s stunning skyline from the water on a private sunset cruise. Enjoy scenic views, BYOB snacks, and a relaxed atmosphere onboard a luxurious sailboat.
Skyline Sunset Cruise
2.5-hour private cruise to watch the sunset over Chicago's historic Skyline.
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About This Adventure
Experience a breathtaking 2.5-hour private sunset cruise on a luxurious 37' sailboat along Chicago's stunning lakefront. Enjoy the city skyline from the water while savoring your favorite BYOB snacks and drinks. With a USCG-certified captain and all amenities provided, this unforgettable happy hour promises relaxation and scenic beauty.
⌚ 2.5-hour Private Lakefront Cruise
⛵ 37' Luxury Sailboat
⚓ USCG-Certified Captain Included
🎡 Departing from the all-new Navy Pier Marina
🥂 BYOB & Snacks
What you'll do
Our private Skyline Sunset Cruise will take you & your guests on a favorable sail along the gorgeous Lakefront, giving a unique experience of seeing the city from the water at sunset. If you're looking for the perfect happy hour in Chicago - this is the cruise for you.
What's Included
✅ USCG-Certified Captain trained in First Aid and CPR.
✅ Private use of our fully-permitted, fully-insured sailing yacht.
✅ Complimentary beverages and snacks on board.
✅ Fully stocked kitchenware, fridge and bathroom.
✅ Stereo surround sound speakers with Bluetooth connection.
✅ Swim platform with ladder, life-jackets, noodles, floaties & towels.
❌ NO Separate captain fee
❌ NO Fuel and docking fee
❌ NO Damage/cleaning deposit
FAQ
🎒 What should I wear or pack?
We do our best to have on board everything you might need, some personal items to keep in mind include:
- Rain jacket or layers for cooler days
- Boat shoes, sandals, or non-black soled tennis shoes
🍾 What food and drink can I bring on the boat?
You may bring any food and beverages of your choosing including beer, wine, champagne, or hard seltzers. We have alcohol for purchase on board or ahead of time and can provide catering for an added fee.
⚡ What if there is bad weather?
If there is current or forecasted lightning or high wind, we make a weather cancellation one hour before your scheduled departure and provide a full refund.
❓ Where is your full list of FAQs?
You can see all of our FAQs here on our website
On A Boat Sailing, LLC
info@onaboatsailing.com
312.619.7858
Adventure Tips
Arrive early for best seating
Getting to the dock early ensures you secure the best spots and a more relaxed start.
Bring your favorite drinks and snacks
Enhance your cruise experience by bringing beverages and small bites to enjoy while sailing.
Dress in layers
Wind can be cooler on the water, so wear layers to stay comfortable during the trip.
Book in advance for weekends
Weekend cruises tend to fill quickly, so reserve ahead to secure your preferred date.
Local Insights
Wildlife
- Gulls
- Herons
History
Chicago’s lakefront has been a vital part of the city’s development since the late 19th century, shaping its maritime culture.
Conservation
Operators strive to minimize environmental impact by adhering to sustainable boating practices and maintaining the water quality.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Sunscreen
Protect your skin during sunny hours on the water.
summer specific
Hat or visor
Shield your face from sun exposure while sailing.
summer specific
Light jacket or windbreaker
Stay comfortable if it gets breezy or cooler along the lake.
spring; fall; winter specific
Camera or smartphone
Capture scenic views and memorable moments from the boat.