$329 – Summer on Lake Michigan: BYOB Sailboat Cruise for 6

Chicago Sailboat Charters
Nathan Kirchhoff
Deal Expert

Why We Love This Deal

Chicagoans know that one of the best ways to enjoy warm weather in the city is to head out to the Lakefront and picnic next to Lake Michigan. We believe there's an even better option: picnicking on Lake Michigan.

With Chicago Sailboat Charters, friends and family can have a BYOB private sailing so that Travelzoo members — whether from far or near — can all experience the Second City's best.

What's Included

  • $329 for one 2-hour Value Sail for six people (reg. $597)
  • Not valid on: Aug. 20-21

Enjoyed This
"The weather was perfect and we enjoyed Captain Rob!"
Sep 4, 2021 - CHICAGO, USA
See All 18 Member Ratings

More Reasons to Go

  • Cruises depart from a private dock at Belmont Harbor within walking distance of the Belmont CTA stop and dock parking (fees apply)
  • Each cruise is captain led, so you don't have to worry about piloting, and can focus on gazing at the Chicago skyline and sharing time with family and friends
  • UrbanMatter recommends Chicago Sailboat Charters as one of the best boat rental options in the Windy City
Refund Policy: No refunds or exchanges allowed. Vouchers will be honored for the original purchase date range only

Online reservations required; subject to availability. Book reservation online. See voucher for booking details. Voucher can be redeemed immediately; valid select dates daily during merchant's operating hours. Online reservations required by Sept. 5, 2022 (and recommended at least 10 days in advance of desired reservation date); subject to availability. A credit card will be required to hold your reservation. Please arrive at least 10 minutes prior to reservation time. Upon arrival, present printed voucher or display in Travelzoo mobile app. Tax, if applicable, and gratuity are not included; an automatic Chicago amusement tax based on the original, non-discounted price of the services provided will be added (paid directly to the merchant). Please tip on the full value; 15-20% is customary for good service. Not valid on: Aug. 20-21, 2022. All sales final. No refunds or exchanges. 10-day rescheduling policy applies; rescheduling/"no-show" fees may be added. Valid for 6 people. Not valid on products. Cannot combine with other offers. Must use in 1 visit. Must be 12 years old or older. Children 11 and younger are permitted; however, each must have an accompanying adult (ages 18 and up). Subject to weather conditions; reservations may be subject to rescheduling. BYOB is allowed, except for red wine; glass bottles are prohibited except for bubbly and white-wine bottles.

45% off

$329 $597


When You Can Go

Select dates daily through Sept. 15

How to Book

After purchasing your Travelzoo voucher, online redemption is required. See voucher for more info.
Enjoyed This
(18 Member Ratings)
Ratings & reviews reflect verified member feedback for Chicago Sailboat Charters over the past 43 months.
4.8 Quality of Service
4.5 Quality of Activity
4.4 Value for the Money
4.3 Ease of Booking
Show Reviews
Enjoyed Most
It was just beginning to get warm, so our trip was a mix of pleasant and cool weather. We had an enjoyable experience with for others who were celebrating a birthday. Each group had their own wine and snacks and enjoyed them and the views. The captain was well informed a provided good information along the voyage.
Walter Sep 04, 2021 Albuquerque, USA
Enjoyed Most
The weather was perfect and we enjoyed Captain Rob!
Vesna Sep 04, 2021 CHICAGO, USA
Enjoyed Most
Other then not being able to be with my friends the captain was very knowledgeable
Other Comments
I was not aware that our party was to be separated We were expecting to be together as it was booked for the same time
Patricia Sep 04, 2021 Twin Lakes, USA
Enjoyed Most
All around perfect day. Captain was fantastic and we just sat back and relaxed. One of my favorite Chicago activities!
Anna Sep 03, 2021 Batavia, USA
Enjoyed Most
Good Times with Captain Charlie
Charles Sep 04, 2021 MOCKSVILLE, USA

More Deals & Tips

Summer on Lake Michigan: BYOB Sailboat Cruise for 6

45% off

$329 $597