CHICAGO · ILLINOIS
The best of Chicago.
The 14 best dinner experiences in Chicago, with honest prices, run times and who you book through. Which ones are worth your time downtown, and what each one actually gets you.
Sunset Lake Michigan dinner cruise from Navy Pier with skyline views, an all-you-can-eat buffet, and DJ dancing for about $89.
Most Popular“All the crew was excellent, food was great. Especially like to thank Mr. Clayton Ramsey for everything he did for me great job Mr. Ramsey”
Chicago Premier Dinner Cruise on Lake Michigan offers a 3-course dinner, skyline views, and DJ music for about 2.5 hours from Navy Pier.
“All was perfect ., the atención , service , dj , food , etc all very good .very happy moments .. . for sure we will come back , thank you guys”
Enjoy a plated 3-course lunch or dinner aboard the Odyssey on Lake Michigan, with 360 views, a DJ, and skyline passes.
“we had a great time. the food was great, the DJ kept the atmosphere very party like. parking is convenient and the kiosk is right outside the exit/entrance to the garage”
Lake Michigan lunch or dinner cruise from Navy Pier with a big buffet, live DJ, rooftop games, and skyline views. Brunch includes bottomless mimosas.
“Omg, this was amazing. The food and service was wonderful!!!!!! We'll be going again.”
City Cruises Chicago River brunch, lunch, or dinner pairs a 3-course meal with glassed-in skyline views and optional narration, DJ, and mimosas.
“Wonderful service and really good food. Free mimosas for the duration and the river and architecture is first rate!!”
A Chicago Lake Michigan fireworks dinner cruise with a buffet, DJ, and Navy Pier views. Smart casual, weather-dependent fireworks, great value.
“Great time on the boat. Food was excellent and our server, Harold, was awesome. Fireworks was very well done.”
Cruise Navy Pier for a plated dinner, DJ music, and fireworks views over Lake Michigan with Chicago skyline landmarks from the decks.
“Last minute decision, and a really nice one , steak was delicious, weather was perfect, DJ played lots of classics , service impeccable. Memories for a lifetime .”
City Cruises Chicago Lake Michigan fireworks dinner cruise from Navy Pier with a buffet dinner, DJ, rooftop games, and skyline views.
“Wish the cruise went out alittle further on Lake Michigan”
VIP dinner at Willis Tower’s Skydeck with a made-to-order deep-dish pizza, skyline views, and after-hours access—Chicago at night.
“Very well organized. We were met in the lobby after registering at the Franklin Street front desk, and escorted to the elevator. During the ride there is an audio/ video presentation. Upon arrival at the 103 rd floor, seating was assigned and dinner was served. Dinner was great and service was wonderful .”
Step into a 1929 speakeasy in Chicago for dinner plus a 90-minute twenties show with comedy and possible audience laughs.
“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…”
2.5-hour Christmas Eve Lake Michigan cruise from Navy Pier with a DJ, 3-course plated dinner, and 360° skyline views.
“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”
Chicago New Year’s Eve dinner cruise from Navy Pier: gourmet buffet, DJ party, Lake Michigan fireworks views, heated decks, midnight champagne.
“The boat was awesome! Great food! Great drinks! Dancing and balloon drop! Only issue was with tickets. Very unorganized and even though we had tickets on our phones you still had to stand in a long line to get paper tickets. WheRead more”
Enjoy a Chicago River dinner cruise with a plated meal, DJ energy, and summer fireworks nights from Navy Pier area.
“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…”
A Mother’s Day dinner cruise on Chicago’s Lake Michigan with a holiday buffet, live DJ, and skyline views from Navy Pier.
“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.”
From the river and the skyline to the gangster trails, the lakefront and the deep-dish counters, every way to spend a day in the city.
