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A sailboat with three people on board, a city skyline in the background, and a clear sky. 1
Four beverage cans and bottles on a countertop. 2
A collection of beverage cans on a countertop. 3
A cozy interior of a boat with a wooden table, cushioned seating, and a small window. 4
A person diving into the water from a boat with a city skyline in the background. 5
By On A Boat Sailing

Reviews

10 out of 10
Exceptional
Free cancellation available
Price is AU$1,542 per traveller* *Get a lower price by selecting multiple travellers
See tickets

Features

  • Free cancellation available
  • 2h 30m+
  • Mobile voucher
  • Instant confirmation

Overview

    • Feel the wind in your hair as you sail along the Chicago Lakefront
    • Enjoy a private sailing experience for up to 7 or 12 guests for added fee
    • Take the helm, jump in the lake, or relax in the sun on deck
    • Sip on complimentary drinks and snacks or bring your own
    • Listen to your favourite tunes with on board surround sound bluetooth speakers

Activity location

    • Chicago
    • Chicago, Illinois, United States

Meeting/Redemption Point

    • 797 E Grand Ave, Chicago, IL 60611, USA | Meeting instruction provided in booking email.
    • Chicago, Illinois, United States

Check availability

Sunset Sailing Charters at Navy Pier Marina

  • Activity duration is 2 hours and 30 minutes2h 30m
    2h 30m
  • English

Our private Skyline Sunset Cruise will take you & your guests on a favourable sail along the gorgeous Lakefront, giving a unique experience of seeing the city from the water at sunset. The perfect happy hour in Chicago!

Language options: English
Starting time: 5:00 PM
Price details
AU$1,541.57 x 1 TravellerAU$1,541.57
Total
Price is AU$1,541.57

Chicago Lakefront Cruise at Navy Pier Marina

  • Activity duration is 3 hours3h
    3h
  • English

Our private Chicago Lakefront Cruise will take you & your guests on a favourable sail along the gorgeous Lakefront, giving a unique perspective on the city's architecture. Take the helm, jump in the Lake or relax on deck to the sound of wind and waves.

Language options: English
Starting time: 2:00 PM
Price details
AU$1,822.11 x 1 TravellerAU$1,822.11
Total
Price is AU$1,822.11

Sail & Swim Playpen Charters at Navy Pier Marina

  • Activity duration is 4 hours4h
    4h
  • English

Enjoy a four-hour private sail and swim charter aboard a meticulously maintained 37' luxury sailing yacht departing from Navy Pier Marina in city centre Chicago. Perfect for summer birthdays and bach parties!

Language options: English
Starting time: 1:00 PM
Price details
AU$2,242.92 x 1 TravellerAU$2,242.92
Total
Price is AU$2,242.92

What's included, what's not

  • Inclusions
    USCG-Certified Captain trained in First Aid and CPR
  • Inclusions
    Private use of a fully-permitted, fully-insured sailing yacht
  • Inclusions
    Complimentary ice, drinks and snacks or bring your own
  • Inclusions
    Fully stocked kitchenware, fridge and bathroom
  • Inclusions
    Stereo surround sound speakers with Bluetooth connection
  • Inclusions
    Swim platform with ladder, life-jackets, noodles, floaties & towels
  • Exclusions
    Catering and drink packages available for added fee
  • Exclusions
    Service charge for captain at 10-20% per level of satisfaction is appreciated

Know before you book

    • Not allowed: Glass objects, High-heeled shoes, Red wine, Unaccompanied minors
    • Not suitable for: People prone to seasickness, People with mobility impairments

What you can expect

  • On A Boat Sailing offers an all-inclusive, VIP sailing experience departing from the brand-new Navy Pier Marina in City centre Chicago. If you appreciate attention to detail, hospitality, and sophisticated service, this is the boat rental for you! Amenities on board include:

    Pricing for private groups up to 7 guests.
    Custom pricing available for larger groups up to 12.
    Anchoring in the Chicago Playpen for swim and float parties.
    Swim platform with rinse shower-lily pad, noodles, life-jackets and floaties.
    Large open cockpit seating area.
    Complimentary drinks and snacks or BYO (alcohol allowed).
    Stereo surround sound speakers with Bluetooth connection.
    Fridge with ice, fully stocked kitchenware.
    Skyline views of City centre Chicago, Navy Pier and the Chicago Lighthouse.
    Anchoring for concerts at Northerly Island.
    Kitchen, bathroom and changing room on board.

    No added fees for fuel, security deposit, cleaning or water toys. Fully licensed, permitted and insured boat operating at the highest safety standards set and maintained by the US Coast Guard. Fuel, complimentary snacks, ice and drinks are included in the quoted cost. Specific requests for provisioning or catering available for additional fee. Charter industry service charge is 10%-20% of the contract cost per level of service and client satisfaction.

Location

Activity location

  • LOB_ACTIVITIESLOB_ACTIVITIES
    • Chicago
    • Chicago, Illinois, United States

Meeting/Redemption Point

  • PEOPLEPEOPLE
    • 797 E Grand Ave, Chicago, IL 60611, USA | Meeting instruction provided in booking email.
    • Chicago, Illinois, United States