Tipsy Cupid Sip & Sail Valentine's Day Yacht Cruise (Chicago)

Name: Tipsy Cupid Sip & Sail Valentine's Day Yacht Cruise (Chicago)
Start: 2026-02-14T18:15:00-06:00
End: 2026-02-14T22:30:00-06:00
Location: Burnham Harbor S Dock (Anita Dee 2)

Skyline Yacht Cruises

Highlights

Sat, 14 Feb, 2026 at 06:15 pm

4.3 hours

Burnham Harbor S Dock (Anita Dee 2)

Starting at USD 39

Date & Location

Sat, 14 Feb, 2026 at 06:15 pm to 10:30 pm (GMT-06:00)

Burnham Harbor S Dock (Anita Dee 2)

1559 S Lakeshore Drive, Chicago, United States

About the event

Tipsy Cupid Sip & Sail Valentine's Day Yacht Cruise (Chicago)

Valentines day Celebration Yacht Cruise, Grab Tickets Asap!! Views!! Fun!! Dancing!!

About this Event

Get Ready Chicago!! – Burnham Harbor
Tipsy Cupid Sip & Sail Valentine's Day Yacht Cruise

#1 Yacht Cruise! 🥳 (21+)
Saturday February 14th, 2026
Location: 1559 S. Lakeshore Drive
(Burnham Harbor), Chicago

Boarding Time: [ 6:15pm ] Departure: 7:00pm Sharp Gates Close
Process to sail off Commences
Sails Till 10:30PM

🎟️ Limited tickets available — early arrival is strongly encouraged!

Set Sail for a Night of Romance/Fun, rhythm, and pure vibes aboard the luxurious yacht departing from Chicago’s iconic Burnham Harbor.

Welcome the New Year and Celebrate Love in Style — whether you’re coupled up, mingling, or just in the mood to vibe! Experience a new wave of clubbing with class, featuring:

🌹 Live DJ & Dancing — the hottest mixes to keep you moving all night

🍸 Full Bar — toast to love, laughter, and new connections

✨ Elegant Yacht Atmosphere — city skyline views, mood lighting, and a romantic ambiance

📸 Photo Ops — capture unforgettable moments with Chicago’s skyline as your backdrop

💎 Onboard Experience:
Once on board, be sure to ask about our Special Perks and New Club Memberships available Exclusively to our Guests — it’s your chance to stay connected and enjoy more Luxury Experiences all Year long.

Dress Code: Upscale casual /Gym Shoes ok or Valentine’s inspired — bring your best look!

((Please Note)) all Bars On every Level Accpet Debit /Credit Cards Or Apple Pay Only))

3 LEVELS OF MUSIC!
2 Heated Indoor Dance Floors / 1 Outdoor Deck
CHICAGO'S HOTTEST DJ NEHPETS FROM POWER 92,
MIXING All Styles of Music To Keep The Party Going All Night!
#1 Chicago Party CRUISE!

Cruise on Chicago waters to celebrate the weekend while enjoying the best views of Chicago!
Unwind from the week and relax on the water while you indulge on breathtaking views of Chicago Insta Worthy Skyline!!

While on board, be sure to check out our fully stocked bar!
Our dance floors are fully heated but we are still rocking open-air!

Your Cruise Experience Includes:
* Scenic 3 hour cruise of the Lake Michigan
* Captivating views of the Chicago skyline including the Navy Pier, The Gold Coast and Much More!
* 3 levels of music (Outdoor Floor of Music ; Two Indoor Floors of Music)

* Live DJ playing all styles of R&B, Hip Hop, Reggae, Latin, Top 40, House & more.

* Rain? No problem, there are two large indoor dance floors and indoor sitting areas!

* Food Available for Purchase ((While Supplies Last) from Food Vendors Sometimes Are Available, Not Guarantee to be on board!!

We do recommend you eat before coming to event!

* Great for Birthday Celebrations / bachelorette / bachelor / anniversary / graduations & more (Balloons & Cakes permitted – no other outside food allowed)

*Is there Seating On The Yacht ? Yes, Reserved Seating Purchased Online, (Tables Limited) And Do Sell Out Quick!!
*Open Seating First come First Serve Located 1st floor Toward the back of the Yacht and Outisde Top Deck.

**Any Swaps To Another Event Will Incur a $10 Restocking Fee Per Person, Fees will Be Applied if you are unable to attend event and are looking to rebook. Tables cannot be carried over to a new event only General Admission.
((MUST CONTACT (773) 712-6998 FOR SWAP PROCESS))

Example: If You Bought A Ten Top Table you can get 10 General Admission Entries Swapped for a new Event , as so long as its not Sold Out , @ $10 per person and Upgrade to a Table For $100 More .

Please Make Sure You Buying The Correct Event Before Purchasing**

((FOR GROUP RATES 10+PEOPLE OR MORE CONTACT (773)712-6998

DRESS CODE: Upscale Casual Attire Is Required!!/Gym Shoes OK

1. THERE IS PARKING AT Burnham HARBOR.
Cost $25 -$27 (Card Only) Big Sign For Anita Dee Parking This way! There are other parking options available in the area this is the closest!
*After Paying -Pull in to parking lot and Veer Off to the left about half Way in & park it’s Steps Away to the docking area & Yacht YOU CANNOT MISS IT!!

2. ENTRY ON BOARD THE YACHT IS STRICTLY DENIED FOR ANY PERSON OVERLY INTOXICATED WITH ALCOHOL OR NARCOTICS!!

ANYONE IN POSSESSION OF WEAPONS, ALCOHOL OR NARCOTICS. WILL BE DENIED ENTRY, THIS INCLUDES MARIJUANA (IT IS ILLEGAL TO POSSES MARIJUANA, IN ANY QUANTITY, ON THE BOAT.

((WE ARE CONSIDERED FEDERAL WATERS WHILE SAILING))

THE BOATS ARE REGULATED BY THE UNITED STATES COAST GUARD AND INDIVIDUALS IN POSSESSION OF MARIJUANA OR OTHER NARCOTICS, ARE SUBJECT TO ARREST)

___THERE IS NO PREGAMING -WALKING TO THE BOARDING LINE OR WHILE STANDING IN LINE WAITING TO BE BOARDED,
ANYONE CAUGHT DRINKING OR SMOKING OF ANYKIND WILL BE DENIED ENTRY BY SECURITY!!

NO REFUNDS -NO CREDITS

((PLEASE LEAVE YOUR PARTY FAVORS AT HOME OR IN YOUR CAR))

3. THERE IS A ZERO TOLERANCE POLICY BEFORE, DURING OR AFTER CRUISES FOR ANY INDIVIDUAL(S) FIGHTING OR EXHIBITING AGGRESSIVE AND VIOLENT BEHAVIOR TO ANY STAFF OR FELLOW PASSENGERS!!

INDIVIDUALS WILL BE DETAINED BY SECURITY AND TURNED OVER TO THE CHICAGO POLICE DEPARTMENT TO BE ARRESTED IMMEDIATELY UPON RETURNING TO DOCK.

INDIVIDUALS WILL BE BLACKLISTED AND DENIED ENTRY TO ANY FUTURE EVENT.

BOARDING INFO
* Boarding will begin 45 minutes prior to scheduled cruise time.

* All guests must be present no later than 15 minutes prior to scheduled cruise time or their spot may be given away. Those who miss boarding will NOT receive a* As soon as boarding is complete, the gate will close @ 7:30pm and the crew will start preparing for departure. No one else will be permitted to board.
* Please be on time, as the boat will leave without you!

DIRECTIONS
The Anita Dee is docked at Burnham Harbor By Soilder Field off of Lake Shore Drive.** Since the Harbor has no real physical address, GPS and online directions are unreliable. Use the maps along with the directions below to get to the boat!

BE SURE TO ALLOW TIME TO PARK AND ARRIVE AT THE HARBOR ON-TIME FOR BOARDING AND DEPARTURE!

Parking apps:
* SpotHero
* BestParking
* ParqEx

Guests may find paid parking at either the South Lot or the Waldron Parking Deck and walk to our location at the South end of the harbor (in between Soldier Field & McCormick Place). See attached map & directions showing our Burnham Harbor location. refund.

🎟️ Ticket Check-In Reminder:
Please have your Eventbrite ticket ready at the door — either on your phone or printed. We recommend bringing a printed copy of your QR code just in case your phone battery or signal isn’t working.

https://cdn-az.allevents.in/events10/banners/326304a0-c4ff-11f0-aa12-1bc58e46eb9e-rimg-w581-h740-dcffffff-gmir.jpg

Rules, Regulations & Disclaimers:
All guests must be 21+ with a valid government issued ID that will be checked by security prior to boarding the boat.

A valid ticket with scannable QR code is required by all guests to board.

It is recommended to print a paper ticket to prevent any technology complications which would prevent your ticket from displaying on your phone.

There is no guest list at the boat, each ticket must be scanned.

Security reserves the right to inspect all bags and persons.

Absolutely no outside food or beverage may be brought on the boat.

Guests who are deemed Overly intoxicated (or otherwise unfit) upon arrival, will be denied entry and no refunds will be given.

We want all guests to enjoy themselves on the cruise, but please note you will be on the boat for an extended amount of time and our number one priority is the safety of all guests.

The boat will depart the dock as soon as boarding is completed. Once the boat begins its cast off procedure, for the safety of all guests, absolutely no late arrivals will be allowed within the security fence to board.

If you are late, you will be left at the harbor without a refund.
In the event of dangerous weather conditions, security situations, mechanical issues with the locks, the boat, etc., the boat may not cruise, but the event will still go on at the dock.

In the event of rain, or other inclement weather, the event will continue on the enclosed portion of the boat.

Any ticketing/technical issues will be handled by Eventbrite.com. Please contact them directly at https://www.eventbrite.com/contact-us/.

Sorry – no refunds or price adjustments. The Eventbrite system does not allow us to restrict people who are underage from buying tickets.
If you are not 21+ and purchase a ticket, you will NOT be allowed on board.

Cruise length Or Sail will vary based upon multiple factors, including, but not limited to: boarding time, lock operations, boat traffic, weather, special events such as fireworks, emergency situations, etc.

The music's volume level will be set to an acceptable level intended to please all guests and may be regulated/limited by safety regulations set forth by the Captain.

For further Terms and Conditions of this event and ticket purchase please see “Ticket Purchase and Event Terms and Conditions” in checkout before purchasing these tickets; which shall also be binding and shall be incorporated by reference as though fully stated herein.

Also check out other Entertainment events in Chicago, Parties in Chicago, Workshops in Chicago.

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Ticket Info

Tickets for Tipsy Cupid Sip & Sail Valentine's Day Yacht Cruise (Chicago) can be booked here.

Ticket type	Ticket price
General Admission Ticket	39 USD
General Admission ONLY Priority Boarding	55 USD
General Admission (20 People Party Pack) NO Table	637 USD
Reserve Table (2 People) + Express Entry	189 USD
Reserved Table for (4 People) + Express Entry	242 USD
Reserved Table for (10 People) Party Package	429 USD