City Cruises Chicago: Premier Lunch or Dinner Cruise

A meal on the water gives you a different view of Chicago: the skyline rises behind the lake, and landmarks such as Navy Pier, Grant Park, and Willis Tower come into view as you cruise. The Odyssey pairs that sightseeing with a seated three-course meal, so the boat ride is as much about dinner and company as it is about taking in the city.

I like two things in particular: the mix of a private dining table and open-air viewing decks, which lets you move between a proper meal and a closer look at the skyline, and the live DJ, which gives the cruise a social, celebratory feel. The menu offers familiar choices, with more elaborate dinner options available for an additional charge.

One consideration: this is a dressed-up meal, not a casual sightseeing boat. The dress code rules out jeans, shorts, T-shirts, sports shoes, and sandals, and music and meal service can vary in quality. You’ll also want to verify the departure details close to sailing, since a departure-point change caused confusion for one party.

At a glance

• Three courses at your own table: Choose a starter, main course, and dessert from the available menu.
• A skyline view from the lake: The route passes notable buildings and waterfront sights, including Willis Tower, Navy Pier, Shedd Aquarium, and Adler Planetarium.
• Indoor and outdoor spaces: Dine inside, then head to the observation deck for 360-degree views.
• A DJ and dance floor: The onboard music adds a party element, though it may make conversation harder at times.
• $88 per person to start: Alcohol and some dinner selections cost extra, so check the final price of your choices.

Boarding at Navy Pier

The cruise departs from Navy Pier, at 600 E Grand Ave. Enter through the pier’s main entrance and follow the south-side dock to the Odyssey, which is located about halfway down. Check in at the Odyssey Lake Michigan ticket booth near the Shakespeare Theatre sign, then collect your boarding passes.

Boarding begins 30 minutes before departure. I’d use that time rather than cutting it close: the pier is a large place, and the operator asks you to check in at the boat’s ticket booth. Take the confirmation and departure instructions with you, and check for updates on the day of the cruise. A date-specific change in departure information caused a near miss for one group, who had to take another Uber after going to the wrong location.

The ship’s photographer may offer to take your picture before you board. Those souvenir photos are available for purchase, so treat this as an optional extra rather than part of the ticket price.

A meal with a view, not a narrated architecture tour

Once aboard, you’ll be shown to a private table for your meal. The three-course format makes this a comfortable choice for a date, birthday, anniversary, or meal with family and friends. You can sit and talk while the boat moves, then step outside between courses or after dessert to see the skyline from the deck.

There is an onboard DJ and a dance floor. That can be a real plus if you want a lively evening, and several birthday celebrations have made good use of the music. If you’re hoping for a quiet meal or a detailed lesson on Chicago architecture, though, this may not be the right fit. The experience includes a live English-language guide, but the available details do not promise a narrated architecture tour. One past diner specifically wished for more commentary about the city’s buildings.

The dance floor and volume also affect the mood. Music that makes a party feel festive can make conversation difficult, especially if it is played loudly. If talking over dinner is the main event for you, consider that trade-off before booking.

What you can order for three courses

The standard meal includes a choice of starter, main course, and dessert. Lunch and dinner menus differ, and the dinner menu has additional options, some at extra cost. The menu can change, so use the choices below as a guide rather than a guarantee.

For a starter, Caesar salad is listed for lunch and dinner. Dinner choices also include lobster bisque, while jumbo shrimp cocktail, a seafood tower, and a half lobster tail are available for an additional charge.

Main courses include jumbo forest mushroom ravioli, oven-baked Atlantic salmon, roasted chicken breast with rosemary and thyme, and braised beef short rib. The dinner menu also lists pan-seared Pacific cod. More premium dinner choices, including filet mignon, prime striploin, and two broiled Maine lobster tails, cost extra.

Dessert choices include Eli’s New York-style cheesecake, sorbet, and fresh-cut fruit with strawberries. Dinner adds triple chocolate mud pie and warm butter cake, with French macarons and champagne chocolate truffles available for an additional charge.

This is a set-menu meal, not a free-for-all buffet. Your ticket covers the three courses, but it does not include alcoholic drinks. Unlimited coffee, hot tea, and iced tea are included. Tell your server about any food allergy before you order, and check the current menu if a particular dish matters to you.

Food and service are a major part of the value, but there can be small inconsistencies. Diners have praised the food and attentive staff, while others have found a dish lukewarm or had to flag down their server after a course arrived late. One lunch party received its main course and dessert behind the rest of the dining room, though the server corrected the delay. Allow room for that possibility rather than planning a tight appointment right after the cruise.

Reading the Chicago skyline from the water

The sightseeing route is part of the meal rather than a series of stops where you get off the boat. You depart and return to 600 E Grand Ave, with the cruise passing points of interest along the Chicago shoreline. The itinerary names the John Hancock Center, Water Tower Place, Lake Point Tower, Navy Pier, Aon Center, 311 South Wacker, Crain Communications Building, Shedd Aquarium, Adler Planetarium, CNA Center, and Willis Tower.

The changing angle is the reward. From the observation deck, you can take in broad views of the city, while the indoor seating gives you a place to return to when you want to eat or get out of the weather. The 360-degree view is particularly useful if you want photos from more than one side of the boat. Bring your phone or camera, but keep in mind that wind and weather can affect how long you want to stay outside.

The listed landmarks range from prominent towers to waterfront destinations. You won’t be visiting the buildings themselves, and the cruise is not a substitute for a walking architecture tour. It is a chance to see many of them together from the water, with the time and comfort of a meal built in.

One practical detail deserves attention: the activity is described as a Lake Michigan cruise, while a past departure was changed to a river option. The information for your sailing should make clear where you board and what route to expect. If anything looks inconsistent, contact the operator before leaving for Navy Pier.

Is $88 a fair price?

At $88 per person, the price buys more than a boat ride: it includes the cruise, three plated courses, a private table, the DJ and dance floor, and unlimited coffee and tea. If you would otherwise book a meal and a separate sightseeing cruise, combining them can make the fare reasonable, particularly for a special occasion.

But this is not a low-cost way to get a skyline view. Alcoholic drinks are extra, as are several premium dishes and souvenir photos. Add those to the ticket price and the total can climb, especially for a couple choosing upgraded entrées and cocktails. I’d look at the base fare as the cost of the meal-and-cruise package, then decide in advance how much you want to spend on add-ons.

The included service fee helps make the listed price easier to compare, but it does not mean all onboard spending is covered. If value is your main concern, choose from the standard menu and treat the outdoor deck, skyline views, and music as part of what the ticket already provides.

Dress for dinner and check the small print

The stated dress code is smart-casual, with jackets and cocktail attire strongly suggested for dinner. Jeans, shorts, tank tops, halter tops, T-shirts, gym or sports shoes, and flip-flops are not allowed. That is a firmer standard than many casual boat trips, so plan your outfit before you arrive rather than hoping the rule is flexible.

The ship is wheelchair accessible. Infants can travel free, but you still need to select the free infant ticket option when booking. If you’re traveling with a group, make one reservation for everyone: separate bookings do not guarantee that you’ll be seated together.

You can cancel up to 24 hours in advance for a full refund, and a reserve-now, pay-later option is offered. Check the available departure times for your date, since the cruise lasts two to three hours. Smoking is not allowed indoors; smoking is permitted only on the outdoor observation decks.

Who should book this cruise?

This is a good match if you want a special meal, a changing city view, and some music without arranging separate activities. Couples celebrating an anniversary, families marking a birthday, and groups who enjoy a social atmosphere may find the combination especially appealing. The staff can make the night feel personal: servers have been praised for being attentive and helpful, with Leslie and Heather among the names that have been singled out.

I’d hesitate if your priority is a quiet dinner, detailed architectural commentary, or a casual dress code. The music, the possibility of uneven meal timing, and the added cost of drinks or premium dishes matter more if you’re expecting a polished restaurant experience in every detail.

Book it if the appeal is a three-course meal with Chicago spread around you, and you’re happy to pay for the setting as well as the food. Before you go, confirm the departure point, dress to the rules, and decide whether you want to spend extra on drinks or dinner upgrades. That small bit of planning helps you focus on the lake and skyline once you’re aboard.

FAQ

Where does the Odyssey depart from?

The cruise departs from Navy Pier at 600 E Grand Ave. Enter through the main entrance and follow the south-side dock to the Odyssey, then check in at its ticket booth near the Shakespeare Theatre sign.

How early should I arrive?

Boarding begins 30 minutes before departure. Allow time to reach the boat and check in at the ticket booth.

How long is the cruise?

The cruise lasts between two and three hours. Check the available departure times for your date.

What is included in the ticket?

The ticket includes the lunch or dinner cruise aboard the Odyssey, a three-course plated meal, the onboard DJ and dance floor, unlimited coffee, hot tea, and iced tea, and the service fee.

Are alcoholic drinks included?

No. Alcoholic drinks are available to purchase onboard.

What should I wear?

Wear smart-casual clothing. Jeans, shorts, tank tops, halter tops, T-shirts, gym or sports shoes, and flip-flops are not allowed. Jackets and cocktail attire are strongly suggested for dinner.

Can infants join the cruise?

Yes. Infants are free, but you need to select the free infant ticket option when booking.

Is the cruise wheelchair accessible?

Yes, the activity is listed as wheelchair accessible.

Can I cancel or pay later?

You can cancel up to 24 hours in advance for a full refund. A reserve-now, pay-later option is also available.