Chicago

13 Best Chicago Dinner Cruises

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.

1.Chicago Signature Lunch Cruise on Lake Michigan

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★ 4.0

“This was for my boyfriends birthday. We came here from DC. This was a ball. The DJ was on point!! The food was amazing! Salmon, Chicken, veggies, pasta, salad.. A table of sweets! The customer service was A1! Everything was a beautiful time! Make sure…”

Check Availability →Read our full review →

3.City Cruises Chicago: Lake Michigan Lunch or Dinner Cruise

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.

★ 4.0

“Note: Meeting place is at the pier where your boat is docked not in Navy pier address (entrance). All in all it was an excellent activity. The staff was excellent!”

Check Availability →Read our full review →

5.City Cruises Chicago: Fireworks Signature Dinner Cruise

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.

★ 4.0

“The location directions on line are misleading. The ship is at the end of Navy Pier as measured from the Taxi Drop off section—not the address. It’s also a really long walk down the pier —keep that in mind if you have mobility issues. You…”

Check Availability →Read our full review →

6.City Cruises: Chicago Fireworks Premier Dinner Cruise

Experience Chicago’s skyline and fireworks from Lake Michigan aboard a luxury dinner cruise with gourmet food, live DJ, and stunning city views.

★ 3.0

“The staff were wonderful and Paul W., our waiter, was awesome. He and the waitress Alaycia, gave me and my date all that we could have imagined. The whole night with the, food, fireworks and the dancing, everything was perfect! Thank you! Also, the touch…”

Check Availability →Read our full review →

8.Chicago Premier Plus Brunch Cruise on the Chicago River

Experience Chicago in style with a 2-hour Premier Plus Brunch Cruise. Enjoy stunning skyline views, chef-curated brunch, bottomless mimosas, and live narration.

★ 4.5

“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…”

Check Availability →Read our full review →

9.City Cruises Chicago: River Architectural Lunch Cruise

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.

★ 4.5

“Friends and relatives had recommended a Chicago river cruise as a great thing to do in Chicago and we decided on a lunch cruise with Odyssey. The service and meal we received was very good! The Guide pointed out several landmark buildings that we would…”

Check Availability →Read our full review →

11.Chicago: Christmas Eve Lake Michigan Gourmet Dinner Cruise

Celebrate Christmas Eve with a scenic Lake Michigan dinner cruise featuring fine dining, city views, and festive entertainment—perfect for a memorable holiday night.

★ 4.8

“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”

Check Availability →Read our full review →

12.City Cruises Chicago: Fireworks Premier Plus Dinner Cruise

Experience Chicago’s skyline and fireworks from the water with this elegant dinner cruise featuring gourmet food, live entertainment, and stunning views.

★ 4.0

“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.…”

Check Availability →Read our full review →

13.Chicago Signature Brunch Cruise on Lake Michigan

Experience scenic Lake Michigan views with a Chicago brunch cruise featuring a buffet, bottomless mimosas, live DJ, and iconic city sights in comfort.

★ 4.5

“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…”

Check Availability →Read our full review →