Music & Event Calendar

Fall Fest

Saturdays from 12PM - 8PM

(starts 9/19 thru 10/31)


Throw on your favorite sweater and enjoy all the activities that Fall has to offer! At Fall Fest on the Riverwalk you'll learn that this season has so much more to offer than pumpkin spiced lattes!

Whether you're looking to get a group of friends together to enjoy some much needed adult beverages or bring the kids out for a stress-free day of fun, this is the perfect destination. This outdoor experience is fun way to catch up with friends and make new ones, all along the beautiful Chicago Riverwalk!

Mimosa Fest

Saturdays from 11AM - 1PM

Sundays from 11AM - 1PM

Enjoy Mimosas from 11am-1pm & French Toast Sticks on the Chicago Riverwalk!


3 mimosa varieties to try:

Orange, Cranberry, Pineapple OR

Gruvi Dry Secco w/ Juices (N/A)

Margarita Fest

Wednesdays from 7PM - 9PM

Sundays from 3PM - 5PM

Enjoy Margaritas for 2 hours, chips & salsa plus fireworks show views on the Chicago Riverwalk on Wednesday nights!


5 margarita varieties to try:

Regular, Mango, Strawberry, Watermelon & THC

Tito's Yappy Hour

Tuesday, September 15, 2026 5:00PM - 7:00PM

Weekly Yappy Hour that is geared towards all furry friends and their parents! Our partners will be giving samples for 21+ guests while dogs can enjoy some free doggie swag!

Music: Frank Liston

Wednesday, September 16, 2026

5:30PM - 8:30PM

Come chill out on our patio and listen to live guitar and the soothing voice of Frank Liston!

Fall Fest Music: InFunktious

Saturday, September 19, 2026

1:00PM - 4:00PM

While InFunktious' sets consist of all covers, they do them in a way that feels new and fresh. Their style would best be described as a blues and rock-driven band that gets funky with elements of jam and jazz thrown in.

Fall Fest Music:

Kevin Presbrey (trio)

Saturday, September 19, 2026

5:00PM - 8:00PM

Blending classic storytellers like Jim Croce, Tom Petty, and Van Morrison with a modern Americana sensibility, KP has quietly built a decades-long career touring and recording since the early 2000s. His music has appeared on MTV, VH1, and Fox, and he has shared stages with Sister Hazel, The Doobie Brothers, Rusted Root, and Big Head Todd & The Monsters.

Music: Kevin Presbrey

Sunday, September 20, 2026

1:00PM - 5:00PM

Blending classic storytellers like Jim Croce, Tom Petty, and Van Morrison with a modern Americana sensibility, KP has quietly built a decades-long career touring and recording since the early 2000s. His music has appeared on MTV, VH1, and Fox, and he has shared stages with Sister Hazel, The Doobie Brothers, Rusted Root, and Big Head Todd & The Monsters.

Pacifico Yappy Hour

(Dog Cartoonist)

Tuesday, September 22, 2026 5:00PM - 7:00PM

Weekly Yappy Hour that is geared towards all furry friends and their parents! Our partners will be giving samples for 21+ guests while dogs can enjoy some free doggie swag!

Music: DJ Papa G

Wednesday, September 23, 2026

4:30PM - 8:30PM

A Chicago DJ since 1997, has been a key figure in the city's Caribbean and sound system scene. Known for his "rock steady" vibes, he’s kept the energy alive and a passion for spreading Caribbean music.

Fall Fest Music:

Stone Cold Killers

Saturday, September 26, 2026

1:00PM - 4:00PM

Stone Cold Killers are Chicago's high-energy tribute to the electrifying sounds of The Killers. From the iconic riff of "Mr. Brightside" to the anthemic pulse of "When You Were Young," the band delivers arena-level performances that capture every hook, every synth, and every soaring chorus.

Fall Fest Music:

Zach Bellas

Saturday, September 26, 2026

5:00PM - 8:00PM

Zach Bellas is a three-piece international touring all-original alternative rock band with an electrifying and exhilarating live show that immediately connects with lovers of authentic Rock n Roll. Fans of the Red Hot Chili Peppers, Tom Petty, Neil Young, Green Day, & The Grateful Dead will instantly recognize their main influences of classic 90's & 70's rock that they effortlessly deliver with a new and fresh interpretation for the modern ear.

Music: Sir Charles & The Mix

Sunday, September 27, 2026

1:00PM - 5:00PM

Come to our Island Oasis for some Island Vibes from Sir Charles on the keys!

Good Boy Vodka Yappy Hour

Tuesday, September 29, 2026 5:00PM - 7:00PM

Weekly Yappy Hour that is geared towards all furry friends and their parents! Our partners will be giving samples for 21+ guests while dogs can enjoy some free doggie swag!

Music: Zach Bellas

Wednesday, September 30, 2026

5:30PM - 8:30PM

Zach Bellas is a three-piece international touring all-original alternative rock band with an electrifying and exhilarating live show that immediately connects with lovers of authentic Rock n Roll. Fans of the Red Hot Chili Peppers, Tom Petty, Neil Young, Green Day, & The Grateful Dead will instantly recognize their main influences of classic 90's & 70's rock that they effortlessly deliver with a new and fresh interpretation for the modern ear.

Fall Fest Music:

Treehorn Duo

Saturday, October 3, 2026

5:00PM - 8:00PM

Treehorn Duo brings together years of jam, funk and rock influences, mixing deep grooves with the loose, live energy of two musicians who know how to play off each other. The name is a nod to The Big Lebowski antagonist Jackie Treehorn—a dated reference, perhaps, but that’s just, like, your opinion, man. And no, we don’t do the Eagles.

Tito's Yappy Hour

Tuesday, October 6, 2026 5:00PM - 7:00PM

Weekly Yappy Hour that is geared towards all furry friends and their parents! Our partners will be giving samples for 21+ guests while dogs can enjoy some free doggie swag!

Fall Fest Music: InFunktious

Saturday, October 10, 2026

1:00PM - 4:00PM

While InFunktious' sets consist of all covers, they do them in a way that feels new and fresh. Their style would best be described as a blues and rock-driven band that gets funky with elements of jam and jazz thrown in.

Pacifico Yappy Hour (Bark-Tober)

Tuesday, October 13, 2026 5:00PM - 7:00PM

Weekly Yappy Hour that is geared towards all furry friends and their parents! Our partners will be giving samples for 21+ guests while dogs can enjoy some free doggie swag!

Fall Fest Music:

Red Delicious

Saturday, October 17, 2026

1:00PM - 4:00PM

Red Delicious, led by singer-guitarist Drew Depke, brings soulful vocals and funky rock ’n’ roll to your favorite hits, giving familiar songs a fresh identity.


Fall Fest Music:

Sir Charles & The Mix

Saturday, October 17, 2026

5:00PM - 8:00PM

Sir Charles and the Mix blends soul, R&B, reggae, pop, and Caribbean grooves into an energetic, feel-good live experience. Led by vocalist and keyboardist Sir Charles, every show is about great music, good vibes, and turning the crowd into part of the experience.

Fall Fest Music:

Midnight Hour

Saturday, October 24, 2026

1:00PM - 4:00PM

Midnight Hour is Chicago’s premier R&B and Soul experience, dedicated to the deep grooves and powerhouse vocals that defined an era. From the grit of Stax and the polish of Motown to the funk of the 70s, we deliver a high-octane set designed to keep the dance floor packed and the energy electric.

Led by seasoned veterans of the Chicago music scene, Midnight Hour isn't just a cover band—it's a celebration of the music that moves people.

Fall Fest Music:

Sir Charles & The Mix

Saturday, October 31, 2026

1:00PM - 4:00PM

Sir Charles and the Mix blends soul, R&B, reggae, pop, and Caribbean grooves into an energetic, feel-good live experience. Led by vocalist and keyboardist Sir Charles, every show is about great music, good vibes, and turning the crowd into part of the experience.

Our Fleet

Enchantment

Ideal Guests - 40 TO 100

Max Guests - 120

Smoking Permitted - Yes

Full Bar On Board - Yes

BYOB - No/BYOF - Yes

Boarding - Chicago Riverwalk

Swiming/Waterslide - No

Air Conditioning & Heat - Yes

Dog Friendly - Yes


Enchantment is great for groups of 40 to 120 people. Featuring full bar, air conditioning, heat, upper and lower cabins along with a large out door area on the bow and upper deck.

Island Time

Ideal Guests - 40 TO 70

Max Guests - 90

Smoking Permitted - Yes

Full Bar On Board - Yes

BYOB - No/BYOF - Yes

Boarding - Chicago Riverwalk & Monroe

Swiming/Waterslide - No

Air Conditioning & Heat - Yes

Dog Friendly - Yes


Island Time has full bar service (available as cash bar or with multiple packages to choose from), premium sound system inside and out on both levels to create the perfect atmosphere. This party boat is equipped with an auxiliary cord that can be used with most phones, computers, or tablets, so you can bring your own favorite music playlists, or let us play DJ and pick the music for you!


Kona & Grand Luau

Ideal Guests - 18 TO 30

Max Guests - 36

Smoking Permitted - No

Full Bar On Board - Yes

BYOB - No/BYOF - Yes

Boarding - Chicago Riverwalk

Swiming/Waterslide - Yes

Air Conditioning & Heat - No

Dog Friendly - Yes


Party on the Big Island. Kona & Grand Luau are 50 foot Tiki/Island themed party boats outfitted for comfort and fun with many conveniences for up to 36 guests (and plenty of Island character.)


Kona & Grand Luau have premium sound systems featuring 8 speakers both inside and out on both levels to create the perfect atmosphere.

Polynesian & Tahitian

Ideal Guests - 6

Max Guests - 6

Smoking Permitted - No

Full Bar On Board - No

BYOB - No/BYOF - Yes

Boarding - Monroe Harbor

Swiming/Waterslide - Yes

Air Conditioning & Heat - No

Dog Friendly - Yes


32 foot (length over all) pontoon Party Boat, with a water slide and plenty of seating for 10 people. Hit the Play Pen Lake Michigan for a dip, or cruise the Chicago River.