Chicago
The dining decks on the lake and river: premier dinner sailings against the skyline, signature lunch cruises and brunch runs out of Navy Pier. The skyline was built to be seen from the water at golden hour; the tables face accordingly.
Enjoy a scenic 2-hour lunch cruise on Lake Michigan in Chicago, with buffet dining, stunning skyline views, live music, and small-group intimacy.
Most Popular“The overall luncheon was extremely nice. From the staff to the meal. If I could criticize anything it would be to make sure the name of the ship is on the tickets or details. We didn't know which ship to board. And we had to…”
Experience Chicago’s skyline with a gourmet meal on a luxurious Lake Michigan cruise, featuring stunning views, live music, and attentive service.
“the ambiance. the host serves everyone was polite and pleasant EXCEPT for the short dark security at the front that works 2/14/25. I was on my phone informing my husband's where we at and he came out of nowhere after I making my way to…”
Experience Chicago’s skyline on a 2-hour Lake Michigan cruise with buffet meals, live DJ, rooftop games, and stunning views. Perfect for a fun, scenic outing.
“The lunch buffet cruise was exceptional. Entertainment (DJ), service staff, nautical staff, food and cleanliness of the ship provided for a memorable experience. Directions listed with the reservation was clear, concise yet detailed.”
Experience Chicago’s iconic architecture with a 2-hour brunch, lunch, or dinner cruise aboard the Odyssey. Enjoy chef-prepared meals and stunning river views.
“I really loved it. My mom and I did it as part of our first trip to Chicago. Shout out to Lesly A. for the amazing service and overall making us feel comfortable. Highly recommend this!”
Experience Chicago's skyline, fireworks, and a delicious buffet on this 2-3 hour dinner cruise starting at Navy Pier. Perfect for celebrations and memorable nights.
“The dinner was great. I enjoyed the fireworks. The staff was great we enjoyed the DJ. We had great seat near the dance floor.”
Experience Chicago’s skyline and fireworks from Lake Michigan aboard a luxury dinner cruise with gourmet food, live DJ, and stunning city views.
“Boarding the Odyssey was very friendly and simple and easy there was maybe only 25% of capacity on the sailing that we went on. The food was average at best and the serving portions were small, which was good I thought. But the music was…”
Experience Chicago’s skyline and fireworks from Lake Michigan with a 3-hour dinner cruise featuring a buffet, live DJ, rooftop games, and stunning views.
“Reserve copa de champagne y fotografia y se pago por dicho servicio pero no se recibio una vez en el yate.”
Experience Chicago in style with a 2-hour Premier Plus Brunch Cruise. Enjoy stunning skyline views, chef-curated brunch, bottomless mimosas, and live narration.
“It was decent. You can arrive 30 to 40 mins early. Pretty views, food options were good. Service was decent and people on the boat made it lively. Lots of opportunities to go out on the bow and back of boat for photos. Recommend doing…”
Experience Chicago's stunning architecture from the water with a 2-hour river cruise that includes a delicious 3-course lunch, guided commentary, and scenic views.
“It was a great department outing for my team and I. I will be back to plan a cruise for private events as well.”
Discover Chicago’s skyline on a 2-hour lakefront brunch cruise featuring scenic views, a buffet, unlimited mimosas, and lively DJ entertainment.
“Disappointed that boat did not have seats outside of the deck to enjoy the beautiful weather and view.”
Celebrate Christmas Eve with a scenic Lake Michigan dinner cruise featuring fine dining, city views, and festive entertainment—perfect for a memorable holiday night.
“Improved- food is hot not cold… soda was very flat and syruppy Not sat near the door -everyone kept opening and shutting the door - it was cold. I wore my puffer jacket for the meal Many songs were in Spanish”
Experience Chicago’s skyline and fireworks from the water with this elegant dinner cruise featuring gourmet food, live entertainment, and stunning views.
“I had an absolutely amazing experience! At first, things started off a bit chaotic! I accidentally purchased my tickets for the wrong date. I panicked, but thankfully I was able to reach out to the vendor and was connected with a wonderful woman named Samantha.…”
Experience scenic Lake Michigan views with a Chicago brunch cruise featuring a buffet, bottomless mimosas, live DJ, and iconic city sights in comfort.
“ALL of the staff were very polite, seemed truly interested in making the occasion personalized, and meeting our every need. The food was delicious, the DJ was able to play our requests, and the facilities were clean and obviously care for very well. No complaints…”
The river runs through an architecture lesson, and the lake applauds.