City Cruises Chicago: Premier Lunch or Dinner Cruise

Chicago’s skyline is best understood from the water, and this cruise gives you a moving front-row seat while you eat. From Navy Pier, the Odyssey passes sights from the John Hancock Center and Water Tower Place to Shedd Aquarium, Adler Planetarium, and Willis Tower. The skyline views are the main event.

I like the polished three-course meal and the chance to see the city from both the dining room and outdoor observation decks. I also like the easy social rhythm: eat first, then listen to the DJ or dance. The main drawback is that this is a dining cruise, not an architecture cruise, so you should not expect much commentary about the buildings.

Key points to know before boarding

• Best view: The outdoor decks offer 360-degree views of Lake Michigan and Chicago’s shoreline.
• Best meal choice: Dinner gives you more elaborate options, including lobster and steak for an extra charge.
• Best atmosphere: The DJ and dance floor make the evening feel more like a celebration than a quiet restaurant meal.
• Dress matters: Jeans, shorts, sandals, sports shoes, T-shirts, and sleeveless tops are not allowed.
• Allow extra time: Boarding begins 30 minutes before departure at Navy Pier’s south-side dock.
• Group tip: Make one reservation for your whole party if you want to sit together.

A restaurant with Chicago moving past the windows

City Cruises Chicago’s Premier Lunch or Dinner Cruise combines a three-course plated meal with a ride along Lake Michigan. The ship, Odyssey Lake Michigan, leaves from Navy Pier and typically spends two to three hours on the water.

You sit at a private table while the onboard kitchen prepares your selected starter, main course, and dessert. Coffee, hot tea, and iced tea are included. Cocktails, wine, beer, and other alcoholic drinks cost extra, as do souvenir photographs and several premium menu choices.

At $88 per person, this is not a cheap way to eat lunch or dinner. You are paying for the meal, table service, music, boat ride, and city views in one package. I think the price makes the most sense for a birthday, anniversary, wedding celebration, or first visit to Chicago when you want one planned experience rather than another meal in a restaurant.

The value is less convincing if your main goal is architecture. You will see plenty of memorable buildings, but the experience is built around dining and atmosphere, not a detailed lecture about Chicago design.

Finding Odyssey at Navy Pier

The cruise departs from Navy Pier, at 600 East Grand Avenue. Enter through the main entrance and walk down the south-side dock. Odyssey is located about halfway along the dock, near the Shakespeare Theatre sign.

Check in at the Odyssey Lake Michigan ticket booth. The yacht’s name is displayed on the front of the boat and above the booth, so you should be able to spot it once you reach the dock. Boarding begins 30 minutes before departure, and arriving early matters because Navy Pier can take longer to cross than you might expect.

Bring a passport or ID card. The information provided for this cruise does not list a specific parking arrangement, but one booking party found parking convenient near the entrance and garage area. If you are using a rideshare, leave enough time for traffic and the walk to the dock.

One practical warning: confirm the departure location close to your sailing date. A recent booking party received conflicting information about a lake departure and a river meeting point, nearly missing the cruise. The stated departure point for this experience is Navy Pier, but last-minute operational changes can happen, so check the latest message from City Cruises before you leave.

What lunch and dinner feel like on board

Once you are seated, the meal follows a restaurant-style sequence. You choose one starter, one main course, and one dessert. Service is intended to be attentive without feeling rushed, although timing can vary.

Lunch is the simpler option and suits you if you want daytime views, a calmer setting, or a shorter celebration. Dinner adds a more formal mood, evening light, and a larger selection of premium dishes.

The standard starter choices include Caesar salad for both lunch and dinner. Dinner also offers lobster bisque, while jumbo shrimp cocktail, a seafood tower, and half a lobster tail are available for an added charge.

Main courses include:

• Jumbo forest mushroom ravioli
• Oven-baked Atlantic salmon filet
• Oven-roasted Frenched chicken breast with rosemary and thyme
• Braised beef short rib
• Pan-seared fresh Pacific cod at dinner

Dinner upgrades include an 8-ounce USDA Choice filet mignon, an 18-ounce USDA Prime striploin, two 5-ounce broiled Maine lobster tails, and other premium additions. These choices can push the final bill beyond the advertised ticket price, so check the surcharge before ordering.

Dessert choices include Eli’s New York-style cheesecake, a duo of sorbet, and freshly cut fruit with strawberries. Dinner adds triple chocolate mud pie and Odyssey signature warm butter cake. French macarons and champagne chocolate truffles cost extra.

The menu is subject to change. If anyone in your party has a food allergy, tell the server before placing the order. That is especially important on a boat, where you cannot simply leave and find another meal nearby.

Food quality appears strongest in the overall presentation and service rather than in every single dish. The salad and desserts have earned particularly warm praise, while the chicken has been described as merely acceptable. Food can also arrive less warm than ideal, and one lunch table had to remind the server when its main course was delayed.

That does not mean you should expect a poor meal. It means you should treat the cruise as a scenic dining occasion, not as a destination restaurant chosen solely for its cooking.

The Chicago skyline from the lake

The route gives you a broad look at Chicago’s eastern edge. From the water, the city’s tall buildings form a more complete picture than they do from a sidewalk, where blocks and traffic often hide the larger pattern.

The stated sightseeing route includes the following landmarks:

• John Hancock Center: This familiar tower anchors the north end of the central skyline and is easy to identify by its strong, dark exterior structure.
• Water Tower Place: The historic Water Tower area marks a change from the tallest modern buildings to one of the city’s older visual landmarks.
• Lake Point Tower: This residential tower near the lake shows how close high-rise living is to Chicago’s shoreline.
• Navy Pier: You begin and end near this major waterfront attraction, giving you a different view of the pier from the lake.
• Aon Center: Its clean, tall profile adds to the central cluster of office towers.
• 311 South Wacker: This downtown building helps fill out the southern part of the skyline.
• Crain Communications Building: Its distinctive sloping roof makes it one of the easier buildings to pick out from a distance.
• Shedd Aquarium: The aquarium sits along the Museum Campus, where the city opens into broad lakefront views.
• Adler Planetarium: Its location at the end of the peninsula gives you a fine angle back toward downtown.
• CNA Center: The red exterior makes this building especially easy to identify among the glass and steel towers.
• Willis Tower: Chicago’s famous supertall landmark closes the route’s architectural roll call, even though it sits farther inland than the lakefront buildings.

Do not expect the boat to pause at every landmark. The pleasure comes from watching the skyline shift as the ship moves, then stepping outside for a wider view. The outdoor observation decks are the place to take in the full scene, but wind and temperature can change quickly on Lake Michigan.

A daytime cruise gives you clearer detail on the buildings and lakefront. An evening sailing adds sunset or city lights, depending on the season and departure time. One couple found the sunset particularly romantic, while a November booking showed the other side of the bargain: the top deck can be very cold.

After dinner, the DJ changes the mood

The cruise starts as a seated meal and gradually becomes more social. A live onboard DJ supplies the music, and there is a dance floor for anyone ready to move after dessert.

This is one of the cruise’s strongest features for celebrations. Birthday parties and anniversaries fit naturally here, and a large group can turn the dinner into a shared event rather than a series of separate tables. The DJ has received strong praise, and the music can make the boat feel festive even when the weather keeps people indoors.

The tradeoff is noise. At least one party found the music too loud for easy conversation, and children using the dance floor can make the space feel less orderly. If you want a quiet anniversary meal with long conversation, ask for a table away from the dance area if that option is available, and consider lunch rather than dinner.

After dining, you can choose among the dance floor, the interior deck, and the outdoor observation decks. I like that you are not required to spend the entire cruise at the table. The boat gives you room to change the pace as the view changes.

Service, comfort, and the small details

The service is a major part of the experience. A server named Leslie has been singled out for attentive, patient care and helpful suggestions. Heather also received specific praise for her work with the onboard team.

That kind of service matters on a cruise because meals are served to many tables at once. The strongest reports describe staff who are friendly and attentive without hovering. Still, the occasional delayed course shows that service may not be perfectly even on every sailing.

The interior areas are non-smoking. Smoking is allowed only on the outdoor observation decks. Bathrooms have generally been found clean, though one party noticed an unpleasant odor.

The ship is wheelchair accessible. Infants are free, but you need to select the free infant ticket option when booking. If your group wants to sit together, make a single reservation for everyone. Separate bookings do not guarantee shared seating.

Dress code and what to pack

The dress code is stricter than the wording smart-casual might suggest. Jeans, shorts, sandals, flip-flops, sports shoes, tank tops, halter tops, T-shirts, gym shoes, and sleeveless shirts are not allowed.

For lunch, neat smart-casual clothing should be a safe target. For dinner, jackets and cocktail attire are strongly suggested. Pack a light layer even in summer if you hope to spend time outdoors. Lake Michigan can feel cool once the boat is moving, and the top deck may be uncomfortable in colder months.

You should also bring your ID. Alcoholic drinks are available for purchase, but they are not included in the ticket price. Coffee, hot tea, and iced tea are included.

Who gets the most from this cruise

I would choose this cruise for a special occasion, a group celebration, or a first Chicago visit when you want a simple evening plan. It works particularly well for couples who enjoy sunset views, families who like music with dinner, and groups that want a shared meal without arranging a restaurant reservation and a separate sightseeing activity.

The cruise is also useful when you want to see the city from a different angle without committing to a long boat tour. Two hours is enough time to eat, look around, hear the DJ, and relax, according to the stated schedule and onboard experience.

I would hesitate to book it if you are a serious architecture fan who wants building dates, design explanations, or a dedicated guide. English-language tour guidance is available, but the experience does not promise a full architectural presentation. One party specifically wished for even a short summary of Chicago’s architecture.

Families should also think about the music level and dance floor. The setting can be fun for children, but the evening may not feel peaceful. Couples seeking intimacy should consider lunch or a quieter dinner sailing rather than assuming every departure will have a romantic restaurant mood.

Is $88 a fair price?

The $88 base price includes the Odyssey cruise, three plated courses, table service, the DJ and dance floor, tea and coffee, and the service fee. That is a reasonable package for someone who values the skyline setting and wants a ready-made celebration.

It is not an all-inclusive fare. Alcohol, souvenir photographs, and several popular dinner items cost extra. Filet mignon, striploin, lobster tails, seafood tower, shrimp cocktail, and premium desserts can all increase the total.

I suggest comparing the price with what you would spend on a waterfront meal plus a separate architecture or sightseeing cruise. If you would pay for both, this package can be good value. If you mainly want a boat ride, a simpler sightseeing cruise will likely suit you better. If you mainly want fine dining, a restaurant gives you more control over menu, noise, and timing.

Free cancellation up to 24 hours before departure and reserve-now, pay-later booking make it easier to plan ahead. Still, check the sailing details and final menu before committing, especially for a celebration.

Should you book the Odyssey cruise?

Book it if you want Chicago views with dinner, music, and a little ceremony. The strongest reasons are the changing skyline, outdoor decks, capable service, and a festive DJ-led finish. It is a pleasant way to mark an anniversary, birthday, or evening in the city without planning every detail yourself.

Skip it if you want quiet, detailed architecture commentary, or a meal where every dish is the main attraction. For the best balance of comfort and scenery, I would choose a warm-weather sailing, arrive early at Navy Pier, dress properly, and reserve one table for the entire group.

FAQ

Where does the Chicago Premier Lunch or Dinner Cruise depart?

It departs from Navy Pier at 600 East Grand Avenue. Enter through the main entrance, walk down the south-side dock, and check in at the Odyssey Lake Michigan ticket booth near the Shakespeare Theatre sign.

How long does the cruise last?

The cruise lasts approximately two to three hours. Check the available departure times when booking.

What meal is included?

Your ticket includes either a plated three-course lunch or dinner, depending on the option selected. You choose one starter, one main course, and one dessert.

Are drinks included?

Unlimited coffee, hot tea, and iced tea are included. Alcoholic drinks are available for purchase and are not included in the ticket price.

Is the cruise wheelchair accessible?

Yes. The activity is listed as wheelchair accessible.

What should I wear?

Smart-casual clothing is required. Jackets and cocktail attire are strongly suggested for dinner. Jeans, shorts, sandals, flip-flops, sports shoes, T-shirts, gym shoes, tank tops, halter tops, and sleeveless shirts are not allowed.

Can children and infants join the cruise?

Infants are free, but you must select the free infant ticket option when booking. The provided information does not list a separate age restriction for other children.

Can I cancel the booking?

You can cancel up to 24 hours before departure for a full refund. The reserve-now, pay-later option allows you to hold a place without paying immediately.