City Cruises Chicago: Premier Lunch or Dinner Cruise

Chicago looks best from the water. City Cruises’ Premier cruise pairs a three-course meal with broad Lake Michigan views, a live DJ, and a moving postcard of the city’s famous shoreline. I especially like the private-table dining and the chance to step outside for 360-degree skyline views after the meal.

The ship leaves from Navy Pier and cruises past landmarks from the John Hancock Center to Willis Tower, with the skyline changing as you move along the shore. The main drawback is that this is a dining event first and a sightseeing cruise second. You will see the buildings, but you should not expect a full architectural tour or detailed narration at every landmark.

The experience costs about $88 per person and lasts roughly two to three hours. That price can make sense for a special occasion, but it is less attractive if your main goal is simply to photograph Chicago from the water.

Key points to know before you book

• The meal is served at your table: You choose a starter, main course, and dessert from the onboard menu rather than collecting food from a buffet.

• Navy Pier is the departure point: Enter through the main entrance, walk down the south-side dock, and find the Odyssey ticket booth near the Shakespeare Theatre sign.

• The best skyline views are outside: The observation decks are where you will get the clearest photos, especially when the weather is mild and the city lights begin to come on.

• Dinner feels more formal than lunch: Smart-casual clothing is required, with jackets and cocktail attire suggested for dinner.

• The DJ changes the mood: After the meal, the interior dance floor and live music can turn a quiet dinner into a party.

• Check the boarding information carefully: One dated sailing had confusion over a changed departure location, so confirm the final instructions before leaving for Navy Pier.

Boarding at Navy Pier and settling in

Your starting point is 600 East Grand Avenue, at Navy Pier. Enter through the pier’s main entrance and continue toward the south-side dock. The Odyssey is located about halfway down the dock, near the Shakespeare Theatre sign.

Look for the ship’s name on the front of the boat and above the ticket booth. You check in there and receive your boarding passes. Boarding begins 30 minutes before departure, and arriving early matters because Navy Pier is large enough to eat up time before you even reach the boat.

A ship’s photographer may offer a portrait before boarding. You can purchase the souvenir photo later, but it is not part of the cruise price. Have your passport or ID card with you, since identification is listed among the required items.

The ship is wheelchair accessible, which makes this option easier for many people than a smaller sightseeing boat. Still, if you have specific mobility needs, it is sensible to contact City Cruises before sailing and confirm the details of the route from the dock to your table.

One practical warning deserves attention. Departure details have caused confusion on at least one sailing, with conflicting information about a lake departure and a river meeting point. Since the advertised experience here departs from Navy Pier on Lake Michigan, read any final update closely and verify the location on the day of your cruise.

The dining room and the three-course meal

Once seated, you order from a three-course menu and receive tableside service. That is a big part of the Premier experience. You are not balancing a plate while searching for a seat, and the meal gives the cruise a proper occasion feel.

The lunch and dinner menus overlap, but dinner offers more choices and several paid upgrades. Starters include Caesar salad, while dinner adds lobster bisque, jumbo shrimp cocktail, a seafood tower, and a half lobster tail. The seafood selections and larger cuts of beef can increase the bill, so check the price before adding anything.

Main courses include:

• Jumbo forest mushroom ravioli
• Oven-baked Atlantic salmon
• Oven-roasted Frenched chicken breast with rosemary and thyme
• Braised beef short rib
• Pan-seared Pacific cod at dinner
• Filet mignon, striploin, and lobster tails for an additional charge at dinner

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

The menu is subject to change, and you should tell your server about food allergies before ordering. Coffee, hot tea, and iced tea are included. Alcoholic drinks cost extra, so couples or families planning several cocktails should add that expense when judging the total value.

The food has generally been a strong point, though not every dish arrives at the same temperature. One lunch sailing had food arrive late, while another account praised the taste but found the meal slightly cool. That suggests a sensible approach: enjoy the setting and service, but do not book this as a substitute for a top restaurant in Chicago.

Service can make a large difference here. Leslie received especially warm praise for being attentive without hovering, and other sailings were described as having polite, helpful staff. For birthdays, anniversaries, and family celebrations, that personal service may matter more than whether the chicken is restaurant-perfect.

What you see along Lake Michigan

The route is a moving view of Chicago’s eastern edge. You do not get off at the sights, so think of this as a skyline cruise with meal service, not a hop-on sightseeing tour.

John Hancock Center and Water Tower Place

The cruise begins with views toward the northern part of the central skyline. The John Hancock Center, now commonly called 875 North Michigan Avenue, is easy to identify by its dark exterior and distinctive structural braces.

Nearby Water Tower Place connects the modern retail side of Michigan Avenue with one of the city’s older surviving landmarks, the Chicago Water Tower. From the boat, you will not study street-level details, but the cluster gives you a useful sense of how Chicago’s lakefront shifts quickly from historic masonry to tall commercial towers.

Lake Point Tower and Navy Pier

Lake Point Tower curves upward near the shoreline and is particularly interesting from the water because its rounded form differs from the straight-sided office blocks nearby. Its position near the lake makes more sense from this angle than from a crowded downtown street.

Navy Pier is both your departure point and one of the recognizable sights along the route. Seeing the pier from the water gives you a different view of its long structure, rides, and public spaces. The downside is that the ship’s exact path and distance from each landmark can vary, so do not expect a fixed photo stop.

Aon Center and the central skyline

The Aon Center is one of the most prominent towers near the lakefront. Its clean, pale exterior helps it read clearly from the water, especially when the sun hits the façade.

This part of the cruise is useful for understanding Chicago’s scale. From street level, individual towers can feel boxed in by blocks and traffic. From the lake, you see how the buildings form a broad wall along the shore, with Grant Park providing an important open break.

311 South Wacker and the Crain Communications Building

As the view shifts toward the central business district, 311 South Wacker becomes part of the inland skyline. It is not directly on the lake, so its appearance works best as part of the wider city panorama rather than as a close-up landmark.

The Crain Communications Building is easier to pick out because of its distinctive diamond-shaped profile. This is the kind of building that benefits from a water view. From a boat, you can compare its unusual outline with the more conventional towers around it.

Shedd Aquarium and Adler Planetarium

The southern turn brings two of Chicago’s best-known cultural buildings into view. Shedd Aquarium sits on Museum Campus and is recognizable by its low, grand form beside the lake.

Adler Planetarium projects farther toward the water, giving it one of the most useful vantage points for skyline photographs. From near this area, you can often frame the city’s towers together with open water in the foreground. If photography is important to you, bring a phone or camera and spend part of the cruise outside instead of remaining at the table for the entire meal.

CNA Center and Willis Tower

The CNA Center and Willis Tower complete the downtown skyline sequence. Willis Tower, formerly called the Sears Tower, remains Chicago’s most famous high-rise landmark and is easy to identify by its stepped form.

The view from Lake Michigan places Willis Tower inland, so it may not dominate the frame from every point on the route. That is part of the charm: you see the tower as one element in a large city panorama rather than as an isolated attraction.

Outdoor decks, music, and the evening mood

After dinner, you can move to the outdoor observation decks or remain inside. The outside areas provide the clearest views and the best chance to watch the skyline change as the ship moves along the shore.

The live DJ supplies the evening’s soundtrack and a dance floor is available. This is a real strength for birthdays, anniversaries, and groups who want dinner to become a social night out. Several memorable sailings involved dancing, a party-like atmosphere, and music that kept the energy high.

The music can also be too loud for some people. If you want a quiet meal and easy conversation, lunch may suit you better than dinner. One account found the music overpowering, and children using the dance floor made conversation harder. The experience can shift from elegant dinner to lively party, depending on the crowd and the DJ.

Weather affects the outdoor part of the cruise. A November sailing was described as chilly on the top deck, so bring an extra layer even when the dock feels comfortable. The interior remains the safer choice in cold weather, but you will miss some of the strongest sightlines.

Smoking is not allowed indoors. Smoking is permitted only on the outdoor observation decks, which is worth knowing when choosing where to sit or stand.

Lunch or dinner: which works better?

Lunch is the calmer choice. Daylight makes it easier to identify buildings, and the shorter, brighter outing can fit well into a sightseeing day at Navy Pier. It is also a good option if you want the cruise experience without the more formal evening dress expectations.

Dinner is the better pick for romance and celebration. Sunset over the skyline can be especially appealing, and the combination of table service, music, dancing, and city lights creates a stronger special-occasion atmosphere. Jackets and cocktail attire are strongly suggested, and jeans, shorts, tank tops, T-shirts, gym shoes, sandals, and flip-flops are not permitted.

The timing is usually two to three hours, which gives you enough time to eat, move around, listen to the DJ, and relax without taking an entire day. A two-hour sailing was considered a comfortable balance for dining and entertainment, though a delayed meal can make the schedule feel tighter.

Is $88 a fair price?

At $88 per person, the fare covers the cruise, three plated courses, tableside service, the DJ, dance floor, unlimited coffee and tea, and the service fee. Alcohol, upgraded menu items, and souvenir photos cost extra.

That is fair value if you would otherwise pay separately for dinner and a skyline experience. You are paying for the setting, the boat, the entertainment, and the convenience of combining everything in one reservation. It is less compelling if you mainly want a narrated architecture tour, a quiet meal, or the lowest-cost way to see the skyline.

The price also works better for a birthday, anniversary, wedding celebration, or visiting family group. Staff have handled special occasions warmly, and the cruise gives a group a shared activity without requiring anyone to plan dinner, transportation between sights, and evening entertainment separately.

Who will enjoy this cruise most?

I would recommend it for couples who want a romantic evening, families celebrating a birthday, and groups who enjoy music with dinner. It also suits first-time visitors who want a broad introduction to Chicago’s shoreline without committing to a full day of sightseeing.

You should choose another option if detailed architectural commentary is your top priority. The route presents major landmarks clearly, but the experience does not promise an extended explanation of Chicago’s buildings. One useful improvement would be a short recorded architecture summary, especially for people unfamiliar with the skyline.

Book lunch if you prefer daylight, quieter conversation, and a less formal setting. Choose dinner if you want the strongest celebration mood, sunset views, and dancing. In either case, reserve the whole party under one booking so the staff can seat everyone together.

Should you book City Cruises Chicago?

Book it if you value the combination of dinner, skyline views, and entertainment more than any single part alone. The best moments come when you finish a course, step outside with a cup of coffee, and see Navy Pier, Museum Campus, and the downtown towers spread across the water.

Skip it if you want a low-cost boat ride, a quiet fine-dining meal, or a guide explaining every building. For everyone else, especially couples and celebratory groups, this is a pleasant way to see Chicago from a fresh angle. Just confirm the departure details, dress properly, arrive 30 minutes early, and leave room in the budget for drinks or menu upgrades.

FAQ

Where does the cruise depart?

The Odyssey departs from Navy Pier. Enter through the main entrance, walk down the south-side dock, and check in at the Odyssey ticket booth near the Shakespeare Theatre sign.

How early should I arrive?

Boarding begins 30 minutes before departure. Arrive early enough to walk through Navy Pier and locate the correct dock and ticket booth.

How long does the cruise last?

The cruise lasts approximately two to three hours. Starting times vary, so check availability for the date you want.

Is lunch or dinner included?

Yes. Your selected option includes either a three-course plated lunch or a three-course plated dinner.

Are drinks included?

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

What should I wear?

Smart-casual clothing is required. Dinner calls for jackets or cocktail attire, and jeans, shorts, tank tops, T-shirts, gym shoes, sandals, and flip-flops are not permitted.

Is the cruise wheelchair accessible?

Yes, the cruise is listed as wheelchair accessible.

Can I cancel the reservation?

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