A lake is a landscape’s most beautiful and expressive feature. It is Earth’s eye; looking into which the beholder measures the depth of his own nature.

-Henry David Thoreau

Let’s take a moment to express our eternal gratitude for Lake Michigan. Gazing at the Lake on a dreary winter day makes things feel brighter. On a crisp, fall day the water’s vibrance is mesmerizing. While on a rainy spring day, crystal drops collide with the Lake’s pristine water, bringing flashes of hope for warm, sunny days to come. And then there is summer — are there enough words to describe the joy? The Lake seems to be Chicago’s life source. A place where calm beauty gracefully intertwines with all of the fun in and out of the water. 

One of our favorite summer time Chi activities is renting a boat to fully embrace the Lake! Chicago Yachting is the ultimate boat rental company based right here in downtown Chicago! They offer a range of private boat rentals that can hold up to 13 people. 



Azimut | 60ft Flybridge

This luxurious double-deck Italian yacht is an exquisite experience from inside out. There are numerous outside lounge spaces on the flybridge, back deck and bow. Premium leather and wood grain finishes are used through out the interior. ‘Trinity’ checks all the boxes for a high-end yacht experience.

‘Liquid Asset’

Sea Ray 440 | 50ft Flybridge

With a step through flybridge, it’s easy to move between the flybridge seating to the bow sun pads. At the back, this boat has a large deck and swim platform. Inside, there’s a huge comfortable lounge area with tons of daylight.

​’My Kinda Party’

Maxum 4100 | 45ft Express Cruiser

Spacious from the cockpit & bow to the interior salon, your guests will be able to mix and mingle throughout the boat. This vessel has a large swim platform and impressive surround speaker system and multiple lounge or seating areas.

‘After Hours’

Sea Ray Sundancer | 41ft Express Cruiser

This well appointed vessel is stunning from inside to out. Beautiful finishes and luxurious seating are found within the very comfortable interior. Outside, you’ll enjoy the sun and water on the swim platform, lounging on the sun pads and listening to music on the new bluetooth surround sound.

‘Big Daddy’

Regal 402 Commodore | 42ft Express Cruiser

This boat has it all for a day out on the water. Soak up the sun on the sun pads on the bow or at the swim platform. You can get some shade in the comfortable cockpit seating on in the inside lounge areas. The brand new sound system has a bluetooth connection.

‘Big Blue’

Mainship Mediterranean | 40ft Express Cruiser

A custom extended swim platform and recently upgraded sound system with lights makes this boat stand out. With bluetooth audio, sun pads, and a bathroom, you’ll have everything you need for a boat party.

‘Big Blue’ and ‘Big Dog’ are the same make & model.

​’Big Dog’ 

Mainship Mediterranean | 40ft Express Cruiser

Loved for its large open seating layout, your whole group can sit together in the cockpit. This vessel is equipped with a bluetooth sound system, bathroom, interior lounge seating, bow sun pads, and a stepped swim platform and ladder. ‘Big Dog’ and ‘Big Blue’ are the same make & model.


You can book your Chicago boat rental here. Start by selecting your date. You’ll be able to choose your boat and see capacity, rates and availability. Saturdays and holidays tend to book up several weeks to months out. During the week, some last minute requests can be accommodated until the day before the desired rental.

Shortly after you book, you will receive a captain contact list of qualified captains who are familiar with the boats. Chicago Yacthing recommends budgeting $100/hr for the captain. See more info about hiring a captain for your boat cruise here.


Lake Michigan Playpen Party

A beautiful day anchored on Lake Michigan offers a unique combination of lively energy and stunning views of the Chicago skyline creating picturesque and unforgettable moments. Consider renting water toys for an extra splash of fun! 

Chicago River Cruise

Immerse yourself in the breathtaking views of the downtown skyscrapers. Glide along the riverwalk and pass the vibrant selection of bars and restaurants. Dock and indulge in some pizza/vino at Pizzeria Portofino and/or delicacies from RPM Seafood. Make your experience unforgettable! 

Navy Pier Fireworks

Experience the magic of Chicago’s unforgettable sunset topped off with fireworks from Navy Pier on Wednesday and Saturday nights! Witness the city light up in a spectacular show best viewed from the water for a mesmerizing evening adventure. 

Private Architecture Tour

Dive into the heart of Chicago’s architectural wonders and rich history from the exclusive perspective of a lovely boat. Enhance your journey by hiring an architectural docent who will tailor a tour to your curiosity!

Reminder to go for it – summer will be over in a flash!

About The Neighborhood Hotel

The Neighborhood Hotel was founded in 2020 by Jonathan Gordon — a travel enthusiast who enjoys spaces that inspire, comfort and fuel. Each suite is well equipped for short and longterm stays (i.e. kitchens, laundry, etc.). The Neighborhood Hotel transforms old buildings with compelling history into well outfitted apartment style hotels that honor the old while representing the now. The vibe is fresh and fun with rooms that are stocked to support everyone from the homebody to the adventurer. The hotels provide a basecamp for the explorer and a sanctuary for the traveler who needs to recharge, reset or just chill. The suites are simple and clean, punctuated with accents that bring the right amount of pop. The Neighborhood Hotel has locations in Chicago: Lincoln Park, Little Italy, West Loop (2025 opening) and Southwest Michigan: New Buffalo and Grand Beach. 

Read about TNBHD in: Architectural Digest, Midwest Living and CN Traveler! 

Connect with @the.neighborhood.hotel on Instagram and LinkedIn! 

About Chicago Yachting

Chicago Yachting is a family-owned business that has been renting boats since 2013. They provide professional and safe Chicago boat rental experiences. Boating in Chicago is an ideal way to connect with family and friends! Cruising along the Chicago skyline and swimming in the Chicago playpen anchorage is like a mini vacation from city life.

We've got news. Great news.
Coming Soon:
The Neighborhood Little Italy
Where welcome drinks come in the form of bold espresso + crisp prosecco. We can't wait
Chi? [Who]
The Neighborhood Hotel
Cosa? [What]
Warmth, bellezza, history. The cornerstones of Italian culture that The Neighborhood Little Italy captures in its third + largest location with 35 suites (Studio - 2 bedrooms).
Quando? [When]
Spring/Summer 2023
Dove? [Where]
In the heart of Little Italy! Here, you're nestled in a neighborhood with an old world feel that seamlessly welcomes the new and modern. Plus, the most bustling parts of the city are just a stone's throw away and easily accessible on foot/public transit! Places like: The Illinois Medical District + Fulton Market + West Loop + UIC + The United Center + the Loop.
Perché? [Why]
To experience fun, adventure, and comfort!
Come? [How]
Our buildings have stories ingrained in the walls (in a non-creepy way) - stories that are meant to be told and shared. The Neighborhood Little Italy was formerly the National Italian American Sports Hall of Fame which honored the greatest Italian-American athletes, broadcasters, and sports workers to benefit athletics in the United States. Once again, we've fallen for a space outfitted with cool history + architecture. Grateful to all of the hard workers and supporters who are turning another NEIGHBORHOOD HOTEL vision/dream into reality!
The Neighborhood Little Italy building design
Rebel House is nailing the design. Soaring ceilings give way to chic urban lofts with sophisticated Italian villa vibes. the top floor's outdoor terraces feature captivating views of the city and the piazza across the street. La vita é bella.
Stay Connected
Keep up to date with all of our latest news!