ChicaGo By Boat cover
CB

ChicaGo By Boat

ChicaGo By Boat: Sail, celebrate, and capture memories on Chicago's Lake Michigan.

5(5 reviews)
event-planner
$$$
DirectionsCallWebsite

About

ChicaGo By Boat is a Chicago marina and sailing charter at 1559 S Lake Shore Dr, offering Lake Michigan adventures. Guests praise Captain Conway for attentive, accommodating service, clean and spacious boats, and memorable sails—from morning and sunset cruises to proposals and special events. Customers describe experiences as best in class, with photo-worthy moments captured by Conway.

Photos

ChicaGo By Boat
1 / 1

Location

1559 S Lake Shore Dr, Chicago, IL 60605, USA

Get directions
Information
1559 South Lake Shore Drive
Chicago, IL, 60605
(833) 312-2628www.chicagobyboat.com/

Is this your business?

Claim ChicaGo By Boat to manage your storefront, respond to reviews, and receive customer leads.

Services

Sunset Sailing Tours

Relaxing evening sails with panoramic views of Chicago's skyline as the sun sets over Lake Michigan.

Private Charters

Exclusive boat rentals for groups, perfect for celebrations, corporate events, or intimate gatherings.

Special Event Sails

Customized experiences for proposals, anniversaries, and other milestones, with photography services available.

Air & Water Show Viewing

Prime viewing charters during Chicago's annual Air & Water Show from the water.

Morning Sailing Adventures

Peaceful morning tours when the lake is quiet, ideal for serene sailing and photography.

5.00 · 5 reviews

Overall rating

5
5
4
0
3
0
2
0
1
0
T

Tatiana

via Google
· 3 years ago

Sailing on Lake Michigan is a true gift of summer. I love being on the water, taking in the views and enjoying sunshine. Morning sails are special, as the lake is quiet and the boats are few. But a good sail is fantastic anytime. I have sailed on SV Nightswimming with Captain Conway multiple times over the last few seasons. It is always a fantastic experience! He sails hard if wind conditions permit, and there is nothing quite like the power of a heeling sailboat. The views are absolutely stunning to boot! All of the customers' needs are anticipated and cared for. ChicaGo By Boat is a fantastic experience that I am fortunate to able to enjoy. HIGHLY RECOMMEND. Best in class.

N

Nicola French

via Google
· 3 years ago

My husband and I grew up sailing on Lake Michigan. We moved away 15 years ago and the lake is the thing we miss most. We met up with friends over Labor Day Weekend and I surprised everyone by booking a sunset sail with ChicaGo By Boat. Booking and communication was excellent. We totally lucked out with the most gorgeous evening of sailing! Highly recommend Conway, he was a lot of fun to sail with. Definitely the highlight of our weekend! Looking forward to sailing with him again.

M

Marty Koppel

via Google
· 3 years ago

We reserved for the Chicago air and water show. We could not have been more pleased with our experience. Captain Conway was so nice and accommodating we could not have asked for anything more the boat was so nice and clean blankets and rain gear provided. Definitely where u should book a charter we r going to book to sail soon

N

Nicole Keri

via Google
· 5 years ago

We had a totally magical time with Captain Conway for a surprise proposal! Beautiful ship, excellent sailing and all around a truly wonderful time. We will definitely book again for other celebrations!

R

Ryan

via Google
· 5 years ago

Captain Conway facilitated the most amazing experience for me and my Fiance on what became our most special night. I proposed to my then girlfriend last month and Capt. Conway was super responsive and accommodating even after a couple last minute changes. I can't forget to mention he's also a great photographer! The boat itself is absolutely gorgeous and spacious. The cabin and deck were super clean and we felt safe and comfortable even admist the pandemic. I highly recommend Capt. Conway's charter for a romantic night out or a friends get together. Either way I can promise you will have a memorable expierence!

More businesses like this

Venue Logic | Weddings | Corporate Events cover image
View details →

event planner

Chicago, IL
V

Venue Logic | Weddings | Corporate Events

Venue Logic | Weddings | Corporate Events operates multiple Chicago event spaces, including Rockwell on the River and Bridgeport Art Center's Skyline Loft. The team provides planning support, in-house bartending, and a curated vendor network. Reviews highlight professional, communicative staff, transparent pricing, and beautiful spaces with skyline views, helping events flow smoothly from planning to day-of.

4.8(21)
Duneyrr Wine and Beer Company cover image
View details →

event planner

Chicago, IL
D

Duneyrr Wine and Beer Company

Duneyrr Wine and Beer Company is a Chicago event venue, pub, bar, and restaurant featuring in-house beer and wine co-fermentation. Located at 2337 S Michigan Ave Floor 1, the two-level taproom offers a welcoming, dog-friendly atmosphere with cheese boards that pair beautifully with wine-inspired beers. Guests can order by phone, explore flights, and take four-packs to-go.

5.0(5)
LM Studio Chicago cover image
View details →

event planner

Chicago, IL
L

LM Studio Chicago

LM Studio Chicago is a stylish event venue on 808 S Michigan Ave, featuring two floors, floor-to-ceiling windows, and a vibrant, artsy interior. Perfect for weddings and celebrations, it sits across from a park with easy photo ops and quick access to the river. The venue is praised for professional staff, thorough planning, top-notch catering, and a seamless, welcoming experience.

5.0(5)
Create at Upscale: Photography Studio Rentals cover image
View details →

event planner

Chicago, IL
C

Create at Upscale: Photography Studio Rentals

Located at 2147 S Lumber St, Chicago, Create at Upscale: Photography Studio Rentals offers well-maintained studios with multiple backdrops and abundant natural light. Reviewers praise friendly, accommodating staff and professional service, with versatile sets that help bring creative visions to life. The space welcomes props, and hosts like Azeez provide reliable, welcoming assistance, plus amenities such as water, speakers, and wifi.

4.8(5)
Anita Dee Yacht Charters cover image
View details →

event planner

Chicago, IL
A

Anita Dee Yacht Charters

Anita Dee Yacht Charters provides standout Chicago yacht experiences for tours, travel, weddings, and events aboard the Anita Dee II. Guests praise clean, well-stocked yachts, attentive crews, and hosts who guide tours of all decks. From skyline backdrop weddings to river and Lake Michigan cruises with shoreline views, the charter delivers memorable, stylish celebrations.

5.0(5)
Chez Event Venue cover image
View details →

event planner

Chicago, IL
C

Chez Event Venue

Chez Event Venue in Chicago is a modern, well-maintained space described as a beautiful blank canvas for weddings, meetings, and events. Reviews highlight seamless planning with Maricar, built-in tables and chairs, a stunning LED wall with lighting, and a versatile layout. The venue's accessibility, nearby hotels, and collaborative planning create a smooth, memorable experience.

5.0(5)
DirectionsCall