Adventure Collective
Water Activities: Chicago Lakefront Cruise—City Views & Sailing - Chicago

Water Activities: Chicago Lakefront Cruise—City Views & Sailing

Chicagoeasy

Difficulty

easy

Duration

3 hours

Fitness Level

Suitable for most fitness levels, no prior experience needed

Overview

Set sail on a luxurious Chicago lakefront cruise and enjoy breathtaking city views from the water. Whether relaxing, swimming, or sightseeing, this private boat experience offers a unique perspective of the Windy City.

Chicago, Illinois

Chicago Lakefront Cruise

Relax & Breathe In The Beauty of Lake Michigan With This 3-Hour Sip & Sail Adventure!

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About This Adventure

Experience the thrill of a private 3-hour lakefront cruise aboard a luxurious 37' sailboat in Chicago. With a USCG-certified captain, you can choose your adventure—sail, swim, or simply relax. Enjoy complimentary snacks and beverages while soaking in stunning city views from the water. An unforgettable sailing experience awaits!


3-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 Chicago Lakefront Cruise will take you & your guests on a favorable sail along the gorgeous Lakefront, giving a unique perspective on the city's world-class architectural landscape. Want to take the helm, jump in the Lake or just relax on deck to the sound of wind and waves? We provide a choose your own adventure. If you're looking for an intimate way to experience sailing 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
  • Bathing suit for swimming

🍾 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


logo On A Boat Sailing, LLC info@onaboatsailing.com 312.619.7858

Adventure Tips

Bring sun protection

Apply sunscreen and wear protective clothing to stay comfortable during the cruise.

Arrive early

Arrive 15 minutes before the departure time for smooth boarding and some time to relax.

Stay hydrated

Drink plenty of water, especially on warm days, to stay energized.

Prepare for water activities

Bring a swimsuit if you plan to swim, and consider bringing a towel.

Local Insights

Wildlife

  • seagulls
  • fish

History

The Chicago Lakefront has been a vital part of the city's development since the 19th century, serving as a hub for recreation and transportation.

Conservation

The cruise operators participate in local water conservation efforts and promote eco-friendly practices to protect Lake Michigan’s ecosystem.

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Adventure Hotspots in Chicago

Frequently Asked Questions

Recommended Gear

Sunscreen

Essential

Protect your skin from sunburn during the cruise.

summer specific

Hat and sunglasses

Essential

Shield your eyes and face from direct sunlight.

summer specific

Swimsuit

Optional for swimming or water activities.

summer specific

Water bottle

Essential

Stay hydrated throughout the cruise.