Chicago · DINNER EXPERIENCES
Every trip has one free afternoon too few. These 15 dinner experiences justify the slot, priced and timed so you can decide in minutes and get back to the fun part of planning.
A 2 to 3 hour Lake Michigan sunset dinner cruise from Navy Pier with an all-you-can-eat buffet and DJ dance party.
“A very pleasant experience, excellent service and the view is impressive. I definitely recommend it.”
Chicago skyline dinner cruise on Lake Michigan with a 3-course chef-plated meal, DJ music, and seasonal fireworks upgrade in summer.
“Hands down the worst meal to be had in the Windy City. Dry, over seasoned proteins, undercooked and over salted vegetables and all served colder than room temperature. Servers & Bartenders were fantastic. DJ S-Rock made the evening fun & our “table-nieghbors” were a delight to chat with & dance the night away. As an apology a meet & greet with the captain was offered. What would have been appropriate would have been to have chef come and apologize for passing off that sub-par slop as a hundred dollar plus dinner.”
3-course lunch or dinner on Chicago’s Lake Michigan with 360 skyline views, a live DJ, and time on deck. From $88.
“Everything was excellent except the music was way too loud. Also the children on the boat took over the dance floor by chasing each other and doing cartwheels and back flips. Later one little girl began screaming and enjoyed it so much she continued to scream for the next almost thirty minutes. Her mother ignored it and no staff member asked her to stop or spoke to her mother. It almost ruined our birthday party because we couldn’t converse. The food was excellent as was the service. We had lovely weather. The bathrooms were very clean.”
2-hour Lake Michigan lunch or dinner cruise from Navy Pier with skyline views, buffet dining, DJ fun, and rooftop games.
“Omg, this was amazing. The food and service was wonderful!!!!!! We'll be going again.”
Glass-walled Chicago River dining cruise with 3-course meal and skyline views. Brunch mimosas, dinner DJ, sometimes Navy Pier fireworks.
“We sailed around the city, and was introduced to the Chicago skyline, and architecture.”
Lake Michigan dinner cruise with a buffet, DJ, and Navy Pier fireworks, plus big Chicago views from the water. Smart-casual dress.
“Food wasn’t good as the beef wasn’t. DJ was bad. Something smelled like sewer in the stairwells and dining area. For the price, I expected a little more upscale cruise.”
A climate-controlled Chicago fireworks dinner cruise from Navy Pier with DJ music, a plated meal, skyline views, and optional cocktails.
“For what the experience costs the service first of all was terrible worst service ever they did not have our table ready and we did not even get our dinners till after the fire works and on top of if it was cold just not good !”
3-hour Lake Michigan dinner cruise from Navy Pier with a chef-prepared buffet, DJ music, and skyline views for fireworks night.
“I liked the fireworks. It felt like they were firing it correctly for our ship's entertainment!”
Skydeck Chicago Pie in the Sky VIP dinner: after-hours skyline views, customized Giordano’s deep-dish, 3 courses, private table.
“It was really great! The pizza was amazing and even though it turned out to be really cloudy on the night of our dinner we still got some amazing pics and moments where the fog would lift. The lad that served us even gave us tickets to come back for free because of the fog. Great time and was def worth it!”
Step into Vito’s Vault in Chicago for a 1929 speakeasy dinner, then a 90-minute twenties stage show with comedy and audience play.
“Absolutely brilliant evening! Vito and the team put on a fantastic night. A small, intimate speakeasy-style bar and restaurant with stunning 1920s-inspired décor. Dinner was delicious, and the service was excellent. The show was outstanding — a perfect mix of amazing singing, lively dancing, and plenty of laughs! Huge thanks to Vito and the team for such a wonderful experience that we both thoroughly enjoyed. Just don’t forget the password 😉 Stephen 🇬🇧”
Chicago Christmas Eve Lake Michigan dinner cruise with a 3-course plated meal, DJ, and 360 skyline views from Navy Pier for $199.
“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”
New Year’s Eve dinner cruise from Navy Pier with a gourmet buffet, DJ party, Lake Michigan fireworks views, and a midnight champagne toast.
“Tudo incrível Só não sabíamos que barco ia .não tinha Internet e o aplicativo não abria e ninguém sabia qual ir Sufoco Mas no barco foi incrível tudo maravilhoso”
Chicago River fireworks dinner cruise with a plated meal, guaranteed table, DJ music, and select-night Navy Pier fireworks on a glass-enclosed boat.
“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. She was truly invested in helping me make my birthday wish come true, and she did just that. The boat ride and dinner were nothing short of a dream. The food was exceptional, and the entire experience exceeded my expectations. My husband and I had the joy of standing on the back deck, soaking in the breathtaking views of the city while watching the fireworks…”
A Mother’s Day dinner cruise from Navy Pier with a holiday buffet, DJ music, skyline views, and indoor comfort on Lake Michigan for about 2.5 hours.
“The dinner cruise started on time. The food was delish. The only thing that was not clear was that there were additional items for sale. The entertainment was good as well.”
New Year’s Eve plated dinner cruise from Navy Pier with Lake Michigan fireworks, rooftop views, open bar options, and DJ dance time.
“Special way to spend New Year's Eve. The city looked great from out on Lake Michigan. The food was quite good and the service was excellent.”
Every kind of day out in the city, and the best of each.
