Chicago · DINING EXPERIENCES
Good dining experiences fill up weeks ahead and the great ones go first. Below: the 14 to book early, what each includes and how they differ.
Depart Navy Pier for a 2 to 3 hour evening cruise on Lake Michigan. You’ll see the Willis Tower, Adler Planetarium, Soldier Field, and more, then enjoy an all-you-can-eat buffet, drinks at extra cost, and a live DJ. Smart casual dress is required.
“A very pleasant experience, excellent service and the view is impressive. I definitely recommend it.”
Spend about 2.5 hours aboard a City Cruises yacht from Navy Pier, with a three-course dinner, tableside service, Lake Michigan views, coffee, tea, and DJ music. I like this for skyline photos and celebrations, but food and service can vary, and drinks cost extra.
“Every other table had fresh tulips and a candle on it, but since I was by myself I didn't get those things. They said they didn't have a table set up for me-party of 1. They only have 1 vegetarian option so if you don't like that one option they they can't make anything else. I got a Read more”
Board the Odyssey at Navy Pier for a two to three hour Lake Michigan cruise with a plated three-course meal, table service, skyline views, a live DJ, and access to outdoor observation decks. Choose lunch for daylight or dinner for sunset and city lights.
“Everything was Wonderful from the beginning to end. The servers and Heather were all great!”
Sail from Navy Pier on a two-hour City Cruises Chicago brunch, lunch, or dinner cruise. Enjoy a prepared buffet, rooftop skyline views, a DJ, dancing, games, and a cash bar. Brunch includes unlimited mimosas, while lunch and dinner offer hearty salads, entrées, and desserts.
“Fantastic! Everything was amazing. ! Wish that was more Latin music played. Had to ask the DJ for a at least 1 bachata song to hit the dance floor. 100% recommended..thank you!!”
Board the glass-enclosed Odyssey near NBC Tower for a two-hour Chicago River dining cruise. Choose brunch with bottomless mimosas, lunch with architecture commentary, or dinner with an onboard DJ. Expect a three-course meal, attentive service, cocktails for purchase, and clear riverfront views.
“Wonderful! A great date night/ family celebration experience; although I was the only single diner, I was made to feel welcomed & included. The entire crew seemed happy & wanted to make sure everything was perfect . Mimmo, the chef, obviously cooks with love- the food was delicious & plated with care. I’m vegetarian & was delighted with my choices ( not to mention the tasty cocktails.) The view from the river was enchanting. My favorite Chicago memory!”
Cruise Lake Michigan aboard City Cruises Chicago for a buffet dinner, skyline views, DJ music, dancing, and Navy Pier fireworks when weather allows. You receive a table for your party, climate-controlled indoor space, and access to outdoor decks. Smart casual dress is required.
“The cruise was great! The bartender is an idiot...$30 for 2 poorly made drinks, don't bother getting drinks”
Board at Navy Pier for a 2.5 to 3-hour Lake Michigan cruise with a plated dinner, DJ, climate-controlled seating, and outdoor decks facing the fireworks. You’ll see Willis Tower, the John Hancock Center, and the Chicago skyline, with coffee, tea, and water included.
“There were 8 of us and I tested positive for COVID and I called and was told that I had tested positive for Covid and that they would only be six of us since two of us tested positive for Covid. They said they would contact me via email and here I’m still waiting on that email. When I call them directly at the Shipp, they said that they would refund me, but [Viator] hasn’t even had the courtesy to return my messages”
Spend about three hours aboard the Spirit of Chicago or Spirit of Navy Pier for a chef-prepared buffet, Chicago skyline views, live DJ music, games, and Navy Pier fireworks when weather allows. You’ll dine indoors, step onto open-air decks, and buy drinks from the cash bar.
“Worst experience ever!!! My flight got delayed due to bad weather and I emailed the activity director to reschedule my cruise and never got a response. I noticed that my tickets were cancelled and never offered to reschedule. I sent another email asked for a refund, reschedule or credit for another time and was denied all avenues. This company kept my $688.00 and no way to get a credit or nothing. They refused to work with me period. I will not be booking anymore trips with this company. The are bad news!”
You’ll ride to the 103rd floor of Willis Tower after public hours, settle at a table overlooking Chicago, and enjoy a custom three-course Giordano’s meal. Choose up to six pizza toppings, a salad, dessert, and a soft drink, then explore the Skydeck and glass Ledge before heading back down.
“I would highly recommend the Skydeck Dinner on the Ledge. It was the perfect location for me to propose to my future wife. Our waiter was very attentive and happily took many pictures plus a video of the proposal. These are memories we will cherish for the rest of our lives. Thank you for the unforgettable evening!”
At Vito’s Vault, you give the password, enjoy a full dinner, and join Vito’s gang for a 90-minute Roaring Twenties revue. Expect singing, dancing, comedy, audience participation, and servers who also perform on stage. The evening lasts about three hours and includes free parking.
“It was very unique! The staff was amazing and stayed in character the entire time. Heads up! It starts when doors open. This was our first speakeasy experience and we thought there would be a 15/30 minute seating window (as with other comedy shows). That wasn’t the case (apologies to the staff❤️). The food was amazing!! We both had steak and it was seasoned to perfection. I ate everything on my plate. The show was hilarious and the actors (who also double as your waiters and waitresses) did an amazing job getting everyone involved. They all worked so hard. Thanks for an amazing night, Vito! 😘”
Spend 2.5 hours aboard Odyssey Lake Michigan, departing from Navy Pier for a Christmas Eve dinner cruise. You’ll have a private table, plated holiday meal, coffee and tea, DJ entertainment, and outdoor deck access for views of Navy Pier, Willis Tower, and Chicago’s skyline.
“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.”
You’ll board a City Cruises boat at Navy Pier at 9:30 pm for about three hours on Lake Michigan. Expect a freshly prepared buffet, live DJ music, indoor and outdoor viewing areas, fireworks when weather allows, and a Champagne toast at midnight. Smart casual dress is required.
“Horrible check-in instructing and meeting point. Security was awful, but the servers and everything were fine. The issue was to get into a bout”
Board near the NBC Tower for a two-hour Chicago River dinner cruise with a plated multi-course meal, climate-controlled seating, DJ music, and skyline views. On Wednesdays and Saturdays from May 29 through August 31, the cruise includes Navy Pier fireworks, weather permitting. Cocktail attire is expected.
“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…”
Board at Navy Pier for a 2.5-hour Mother's Day dinner cruise on Lake Michigan. Expect a holiday buffet, skyline views, live DJ music, dancing, outdoor decks, and unlimited coffee, tea, and iced tea. Alcohol costs extra, and your party is not guaranteed one table.
“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.”
Pick a river, a sidewalk or a plate.
