Music & Event Calendar
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๏ปฟ
Music: InFunktious
Wednesday, July 29, 2026 5:30PM - 8:30PM
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.
Music: Sir Charles & The Mix
Thursday, July 30, 2026 4:30PM - 8:30PM
Come to our Island Oasis for some Island Vibes from Sir Charles on the keys!
Music: DJ Papa G
Friday, July 31, 2026 4:00PM - 8:00PM
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.
Music: DJ Corey Bless
Saturday, August 1, 2026 4:00PM - 8:00PM
Catch some Island beats by our resident DJ and featured TBA guest DJs every Saturday from 4pm until 8pm!
Music: Sir Charles & The Mix
Sunday, August 2, 2026 2:00PM - 6:00PM
Come to our Island Oasis for some Island Vibes from Sir Charles on the keys!
Music: Frank Liston
Wednesday, August 5, 2026 5:30PM - 8:30PM
Come chill out on our patio and listen to live guitar and the soothing voice of Frank Liston!
Duck Derby + After Party
Thursday, August 6, 2026 12:00PM - 4:00PM
The duck drop takes place off the Columbus Drive Bridge in downtown Chicago, Illinois. The event is FREE to attend, and it costs $10 to adopt a duck and enter the race!
- Duck Drop: 1:00 pm
- Derby After Party: 12:00 am - 4:00 pm
- Join us for live music, samples by various partners & a good ol' ducking team!
Adopt a Duck & Join the Island Party team!
We will be donating 15% of all proceeds from the following towards Special Olympics Illinois:
Tiki Ducks (ask you bartender/server!) & Riverwalk Rambler cocktails.
Music: Sir Charles & The Mix
Thursday, August 6, 2026 12:00PM - 4:00PM
Come to our Island Oasis for some Island Vibes from Sir Charles on the keys!
Music: Stone Cold Killers
Thursday, August 6, 2026 6:30PM - 8:30PM
Delivering hit-pack rock and alternative anthems from Stone Temple Pilots, Coldplay, The Killers, and other great artists!
Music: DJ Papa G
Friday, August 7, 2026 4:00PM - 8:00PM
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.
Music: DJ Corey Bless
Saturday, August 8, 2026 4:00PM - 8:00PM
Catch some Island beats by our resident DJ and featured TBA guest DJs every Saturday from 4pm until 8pm!
Music: Flip D
Sunday, August 9, 2026 1:00PM - 5:00PM
Flip D brings an energetic mix of classic rock, blues & contemporary pop to the stage. With a repertoire that ranges from timeless hits to nostalgic one-hit wonders, Flip D delivers a dynamic performance tailored for any crowd.
Tito's Yappy Hour
Tuesday, August 11, 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: InFunktious
Wednesday, August 12, 2026 5:30PM - 8:30PM
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.
Music: Dead Eye Ry
Thursday, August 13, 2026 4:00PM - 8:00PM
A solo artist from Kenosha Wi. Influential mix of rock both modern and classic and country and 90s sound.
Music: Sir Charles & The Mix
Friday, August 14, 2026 4:00PM - 8:00PM
Come to our Island Oasis for some Island Vibes from Sir Charles on the keys!
Music: DJ Corey Bless
Saturday, August 15, 2026 4:00PM - 8:00PM
Catch some Island beats by our resident DJ and featured TBA guest DJs every Saturday from 4pm until 8pm!
Music: Greg Cone
Sunday, August 16, 2026 2:00PM - 6:00PM
Greg is an acoustic guitarist and harmonica player who brings Caribbean rock vibes to every performance. His blend of sun-soaked sounds of Jimmy Buffett, reggae rhythms of Bob Marley, and many other festive tropical tunes is all about island energy and good times.
Pacifico Yappy Hour
๏ปฟ(Customize Dog Collars)
Tuesday, August 18, 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: Sir Charles & The Mix
Wednesday, August 19, 2026 4:30PM - 8:30PM
Come to our Island Oasis for some Island Vibes from Sir Charles on the keys!
Music: DJ Papa G
Thursday, August 20, 2026 4:00PM - 8:00PM
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.
Music: Chris Johnson
Friday, August 21, 2026 4:00PM - 8:00PM
โChris Johnson Experience is a fresh and exciting musical project led by Chris Johnson, delivering a dynamic blend of Top 40 hits, pop, rock, and timeless classics. Each performance strips the music down to its heart—lyrics, chords, and rhythm—allowing the true essence of every song to shine through. Whether it’s a modern hit with a unique twist or a beloved classic rediscovered, audiences are guaranteed an unforgettable musical journey.
Music: DJ Corey Bless
Saturday, August 22, 2026 4:00PM - 8:00PM
Catch some Island beats by our resident DJ and featured TBA guest DJs every Saturday from 4pm until 8pm!
Good Boy Vodka Yappy Hour
Tuesday, August 25, 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: InFunktious
Wednesday, August 26, 2026 5:30PM - 8:30PM
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.
Music: InFunktious
Thursday, August 27, 2026 5:00PM - 8:00PM
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.
Music: Kevin Presbrey
Friday, August 28, 2026 4:00PM - 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: DJ Corey Bless
Saturday, August 29, 2026 4:00PM - 8:00PM
Catch some Island beats by our resident DJ and featured TBA guest DJs every Saturday from 4pm until 8pm!
Music: Sir Charles & The Mix
Sunday, August 30, 2026 1:00PM - 5:00PM
Come to our Island Oasis for some Island Vibes from Sir Charles on the keys!
Lagunitas Yappy Hour
Tuesday, September 1, 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 Corey Bless
Saturday, September 5, 2026 4:00PM - 8:00PM
Catch some Island beats by our resident DJ and featured TBA guest DJs every Saturday from 4pm until 8pm!
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!
Pacifico Yappy Hour
๏ปฟ(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!
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!
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!
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!
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.
