CHICAGO · ILLINOIS
The best of Chicago.
The 14 best dining 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“Dinner buffet was good, due to weather the boat stayed docked. Please check the weather before scheduling if you’re really expecting to cruise.”
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.
“I wanted to love this experience; however, the cruise was very underwhelming. CONS 1. There is no way of finding the boat without walking up to every boat/ the entire pier 2. The crowd was mostly 50+ 3. No one was dancing. When my friends and I started dancing, we Read more”
Enjoy a plated 3-course lunch or dinner aboard the Odyssey on Lake Michigan, with 360 views, a DJ, and skyline passes.
“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…”
Lake Michigan lunch or dinner cruise from Navy Pier with a big buffet, live DJ, rooftop games, and skyline views. Brunch includes bottomless mimosas.
“The cruise was not on the right boat as paperwork.”
City Cruises Chicago River brunch, lunch, or dinner pairs a 3-course meal with glassed-in skyline views and optional narration, DJ, and mimosas.
“We sailed around the city, and was introduced to the Chicago skyline, and architecture.”
A Chicago Lake Michigan fireworks dinner cruise with a buffet, DJ, and Navy Pier views. Smart casual, weather-dependent fireworks, great value.
“This was breathtaking! The food was so good and the customer service was top notch. Shout out to Tish for taking care of us. The icing on the cake was the fireworks and the live singer on the top deck. Please experience this cruise. It’s worth the money.”
Cruise Navy Pier for a plated dinner, DJ music, and fireworks views over Lake Michigan with Chicago skyline landmarks from the decks.
“Once on the ship and seated we sat for almost 30 minutes and had no been approached by a single waitress or person. Finally I got up and told the manager who apologized and sent another staff member over. He did comp our drinks but the whole vibe was just off for us. The food…”
City Cruises Chicago Lake Michigan fireworks dinner cruise from Navy Pier with a buffet dinner, DJ, rooftop games, and skyline views.
“The bat was not staffed week but the food was great, dj rocked”
VIP dinner at Willis Tower’s Skydeck with a made-to-order deep-dish pizza, skyline views, and after-hours access—Chicago at night.
“It was a really good time and romantic. My wife was really impressed. I really liked that the table is right to the edge of the wall out window ledge. I was not impressed by the building greeters when u first enter the building. They told us to wait outside until exactly 10:30. Then we…”
Step into a 1929 speakeasy in Chicago for dinner plus a 90-minute twenties show with comedy and possible audience laughs.
“It’s a Roaring Twenties experience with dancing and singing. There are also lots of jokes and gags with customer participation.”
2.5-hour Christmas Eve Lake Michigan cruise from Navy Pier with a DJ, 3-course plated dinner, and 360° skyline views.
“Muy divertido! La cena muy rica y el DJ genial. las vistas a la ciudad desde el lago fueron increíbles! Muy recomendable. El staff muy amable.”
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.
