Top 5 Holiday Cruises in ChicagoJulie Caion December 14, 2021 at 2:19 pm

Just because it’s winter doesn’t mean cruises take a back seat on your plans. Cruises are some of the most magical experiences you can have during this season, and that’s why we’ve gathered the best Christmas and holiday cruises in Chicago for you!

Imagine being out on Lake Michigan or the Chicago River with great entertainment, food, and booze with fireworks to end the night. Sounds like a great way to spend the holidays!


200 N. Breakwater Access, Chicago, IL 60601


WHEN: Dec. 18, 8-11 p.m.

Celebrate Christmas early with a cocktail cruise along the beautiful Lake Michigan aboard Anita Dee II. Boarding at Dusable Harbor, the three-story, 140-foot luxury yacht will bring you to breathtaking views of Chicago’s iconic skyline and landmarks. Enjoy the sights in the climate-controlled interior decks or chill out on the open top deck.


The adults-only cruise includes full bars with beer, wine, and cocktails. Your tickets also include over $200 in free bites, like up to $30 in DoorDash cash, $10 of Bitcoin from Coinbase, and $10 credit from Ritual. There will also be a DJ spinning classic party hits and pop music for the crowd. 

A photo contest at the end of the cruise includes prizes like tickets to tasting festivals, skyline cruises, and more. Tickets start at $30 and include a Santa hat for added festivities.


600 E Grand Ave, Chicago, IL 60611


WHEN: Dec. 24, 7-9:30 p.m.

Enjoy a merry Christmas Eve dinner with your loved ones on Lake Michigan. With festive decor, a plated dinner, entertainment, and spectacular views, you’re in for a grand time for the holidays. 

The 2.5-hour cruise sails off from Navy Pier, a Chicago icon in itself. The cruise includes freshly prepared entrees, salads, and desserts, unlimited non-alcoholic beverages, and holiday music. You can also indulge in the yachy’s well-stocked cash bar if you’re in need of libations. Semi-formal attire is recommended for this dinner party.

Tickets are $118.71 for adults and kids ages 3-12 and free for kids ages 2 and under. For an extra special treat with a guaranteed window table, tickets are $143.71.

600 E Grand Ave, Chicago, IL 60611

WHEN: Dec. 31, 11:30 a.m.-1:30 p.m.

Start off the New Year’s Eve festivities with a lunch cruise on the lake! Departing from Navy Pier, the 2-hour cruise will take you through the best views of Chicago. The cruise includes a freshly prepared lunch buffet and unlimited coffee, hot tea, iced tea, and water. A cash bar is also available with creative cocktails, wine, and beer. Onboard entertainment and holiday decor like party hats and favors add to the celebration.

Tickets are $59.90 for adults, $44.90 for kids ages 3-12, and free for kids ages 2 and under. For a guaranteed window table, tickets are $74.90 for adults. The dress code is casual, so nice jeans, khakis, and dresses are advised.

455 N Cityfront Plaza Dr, Chicago, IL 60611

WHEN: Dec. 31, 9:30 p.m.-12:30 a.m.

Count down to midnight in style and luxury with this festive dinner cruise on the Chicago River. You get a front-row seat to the city’s fireworks to ring in the new year and the best views of Chicago. The 3-hour dinner cruise includes a 3-course plated dinner, dessert, and an open bar. Onboard entertainment, party hats, and favors are also included.

Tickets are $299.90 for the Silver Package, $359.90 for the Gold Ticket Package, and $409.90 for the Platinum Ticket Package. The dress code is semi-formal and it’s New Year’s Eve, so come decked out in glitz and glam!

600 E Grand Ave, Chicago, IL 60611

WHEN: Jan. 1, 1-3 p.m.

Start the new year on a happy note with this 2-hour brunch cruise on Lake Michigan. A delicious buffet featuring brunch favorites, both savory and sweet, is here to nurse your New Year’s Eve hangover or just get you energized and ready to tackle any New Year’s resolutions. No hangover? There’s unlimited mimosas! Non-alcoholic beverages like coffee, hot and iced tea, and water are also available.

Tickets are $81.90 for adults, $66.90 for kids ages 3-12, and free for kids ages 2 and under. It’s $101.90 for a guaranteed window table. Come in your casual clothes because you’ll be filling your stomachs with yummy grub! More NYE cruise options here!

Featured Image Credit: Chicago Cruise Events

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