We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
About ChicaGo By Boat
ChicaGo By Boat offers Chicago's premier affordable luxury boat charters. We invite private groups of up to six passengers aboard the S/V Nightswimming for two to three hours based on our guests' needs. Whether it's your first time, only time or just the next time; we want your sailing experience with us to be the BEST time you have this Summer.
Open Now
Hours Today: 9:00 AM - 10:00 PM
Travelers talk about
Improve This Listing

ChicaGo By Boat
Booking unavailable on TripAdvisor

Want other options you can book now?
Reviews (10)
Filter reviews
10 results
Traveler rating
Traveler type
Time of year
Traveler rating
Show reviews that mention
All reviews lake michigan captain sail skiing aboard city
Selected filters
Updating list...
1 - 10 of 10 reviews
Reviewed September 15, 2019

My husband received this as a Father's Day gift and we decided to make it the highlight of a getaway weekend in the city. It was perfect - such a unique way to see the city. Captain Conway was waiting for us at the gate...More

Date of experience: September 2019
Thank 03040810
Reviewed September 5, 2019 via mobile

Excellent experience and outstanding service. Great way to spend quality time with co-workers. Look forward to taking my family on a tour with Captain Conway.

Date of experience: September 2019
1  Thank JDJ205
Reviewed July 16, 2019

I bought this Groupon as a gift for my mom who was celebrating her 10 year anniversary. The booking for the charter was easy and even over a holiday weekend. The day of the sail, Captain Conway reached out asking to postpone the sail by...More

Date of experience: May 2019
1  Thank Sydney L
Reviewed June 25, 2019

Great Captain!! Fantastic and friendly with kids. Easy communication and schedule. Great boat, we had a wonderful time and it started to rain a little and the Captain was prepared with jackets for all! 100% recommended!

Date of experience: June 2019
1  Thank Trip543508
Reviewed May 27, 2019

We had a wonderful time sailing on lake Michigan!! Everything was perfect! Thank you for a great birthday celebration!

Date of experience: May 2019
1  Thank Argentinadelsur1973
Reviewed August 26, 2018 via mobile

Captain Conway is a wonderful host. Also very flexible with scheduling and trying to work us in for the weekend. My friends and I had a blast on a charter sail and would love to do it again next time we are in town. Very...More

Date of experience: August 2018
1  Thank evrigsby
Reviewed August 23, 2018

We had such a wonderful time on Captain Conway's sailboat!!! He and Tatiana made our Air and Water Show experience amazing. The boat was awesome and they both made us have a lovely time on Lake Michigan. We will definitely keep ChicagGo by Boat in...More

Date of experience: August 2018
1  Thank Kk52088
Reviewed August 12, 2018

Trust Capt, Conway and ChicaGo By Boat for all of your sailing needs! Sailing is kind of my thing. There's nothing like relaxing out on the water with friends as we enjoy the inspiring views of Chicago. I'm not talking about a booze cruise. Sure,...More

Date of experience: July 2018
Thank AkashaLin
Reviewed June 19, 2018 via mobile

We booked a private Saturday fireworks sail with ChicaGo By Boat. It was a perfect evening! We drove in from the suburbs. Parking was easy in the lot next to the harbor. Captain Conway navigated us through the gorgeous Chicago skyline and the fireworks are...More

Date of experience: June 2018
1  Thank appease2you
Reviewed May 6, 2018 via mobile

When booking charters two things are non-negotiable: 1. A Savvy Captain 2. A Flawless Boat I have been renting summer charters in Chicago since 2004 and have seen more than a few duds. We stumbled upon Captain Conway several years ago and have asked for...More

Date of experience: May 2018
Thank Vince B
View more reviews
Questions & Answers
Get quick answers from ChicaGo By Boat staff and past visitors.
Note: your question will be posted publicly on the Questions & Answers page.
Posting guidelines