City Cruises Chicago: Premier Lunch or Dinner Cruise

Chicago’s skyline looks best from the water, and this cruise gives you a seat, a meal, and a moving view of the city in one package. From the Odyssey, you can watch the John Hancock Center, Willis Tower, Navy Pier, and the lakefront unfold from several angles, then head outside for 360-degree views.

I like the mix of a proper three-course meal and a live DJ, especially for birthdays, anniversaries, and an evening that needs a little ceremony. I also like the relaxed two to three-hour length, which leaves time to eat, dance, and take in the skyline without turning dinner into an all-night affair.

The main catch is that this is a dining cruise first and a sightseeing tour second. You get fine views, but there is no promised architectural commentary, and the music can be loud. Add a strict dress code, extra charges for drinks and some dinner dishes, and the value depends on how much you want the setting.

Key points to know before boarding

• Board at Navy Pier: Enter through the main entrance, walk along the south-side dock, and find the Odyssey ticket booth near the Shakespeare Theatre sign.
• Choose lunch or dinner carefully: Lunch is generally more casual, while dinner offers lobster, steak, and extra dessert choices at added cost.
• The skyline is the star: Look for Navy Pier, Grant Park, Shedd Aquarium, Adler Planetarium, Willis Tower, and the lakefront towers.
• Plan around the dress code: Jeans, shorts, sandals, flip-flops, gym shoes, tank tops, and sleeveless shirts are not allowed.
• Expect music, not a quiet restaurant: A live DJ and dance floor create a party mood, though the volume may make conversation difficult.
• Reserve your whole group together: One reservation is the safest way to ensure everyone sits at the same table.

Boarding the Odyssey at Navy Pier

Your cruise begins at 600 East Grand Avenue, at Navy Pier. Enter through the pier’s main entrance and walk down the south-side dock. The Odyssey is about halfway along the dock, with its name displayed on the front of the boat and above the ticket booth near the Shakespeare Theatre sign.

Arrive well before departure. Boarding begins 30 minutes before sailing, and you need to check in at the ticket booth to receive your boarding passes. This is not the moment to cut things close. Navy Pier is large, and the walk from the entrance to the boat takes time, especially if you are meeting a group or stopping to find the right dock.

A ship photographer may take your picture before boarding. Souvenir photos are available for purchase, so you can simply decline if you are not interested. Alcoholic drinks are also available to buy onboard, while coffee, hot tea, and iced tea are included.

One practical warning is worth taking seriously: check your final departure information on the day of the cruise. A change in departure details caused major confusion for one passenger, who went to the lakefront location mentioned in a later email and nearly missed the boat. The listed departure for this experience is Navy Pier, but any updated message should be read closely and confirmed if it conflicts with your booking details.

What the three-course meal is really like

Once seated, you have a private table and tableside service. The meal is plated rather than buffet-style, which gives the cruise a more polished restaurant feel. The schedule is built around the courses, so you can eat while the Chicago shoreline moves past the windows.

Lunch and dinner share several choices. Starters include Caesar salad, while dinner adds lobster bisque. Dinner guests can also pay extra for a jumbo shrimp cocktail, seafood tower, or a two-and-a-half-ounce half lobster tail.

Main courses include jumbo forest mushroom ravioli, oven-baked Atlantic salmon, oven-roasted Frenched chicken breast with rosemary and thyme, and braised beef short rib. Dinner adds pan-seared Pacific cod, with premium choices such as an eight-ounce USDA Choice filet mignon, an 18-ounce USDA Prime striploin, or two five-ounce broiled Maine lobster tails for an additional charge.

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 gives you enough choice for different tastes, but it is not a fully customized dining experience. Menu items can change, and anyone with a food allergy should tell the server before ordering. That advice matters on a moving boat, where last-minute substitutions may be less simple than they are in a regular restaurant.

Food quality appears to be one of the stronger parts of the experience. The salad and desserts receive especially warm praise, while the chicken earns a more mixed assessment. One lunch passenger had to wait for the main course after other tables had reached dessert, although the server corrected the problem quickly.

You should also keep your expectations realistic about temperature and timing. Food has occasionally arrived cooler than ideal, and service can slow during busy sailings. Still, the table service, friendly staff, and meal format are central reasons to choose this cruise over a simple sightseeing boat.

Reading Chicago’s skyline from the lake

The boat’s route gives you a different view of familiar Chicago buildings. From street level, the skyscrapers can feel packed together. From Lake Michigan, the city opens into a long wall of architecture, with the water giving you room to see the shapes and height of the buildings.

The route includes several notable sights:

• John Hancock Center: Look toward the north end of the skyline for this tall, dark tower near the Magnificent Mile.
• Water Tower Place: This shopping complex sits near the historic Water Tower and helps mark the northern edge of the central downtown district.
• Lake Point Tower: Its curved form is easy to spot near the lakefront, where residential buildings meet open water.
• Navy Pier: You begin and end near this major lakefront attraction, with its long pier extending into the lake.
• Aon Center: This tall white tower is one of the most recognizable buildings in the central business district.
• 311 South Wacker: Look for its distinctive rounded, clustered form among the downtown towers.
• Crain Communications Building: Its diagonal grid gives it a memorable diamond-like outline.
• Shedd Aquarium and Adler Planetarium: These lakefront institutions offer some of the clearest views back toward the downtown skyline.
• CNA Center: Its bright red exterior makes it easy to pick out among the surrounding towers.
• Willis Tower: Formerly known as the Sears Tower, it remains the skyline’s most famous high-rise and is best appreciated from a distance.

The observation deck is the place to go when you want the full effect. You can see the skyline, lake, and shoreline without a window between you and the view. Wind and weather will shape how long you stay outside, so bring a layer even on a pleasant day.

The sightseeing is visual rather than heavily narrated. If you want dates, architectural facts, and a running explanation of every building, this is not the strongest choice. The value comes from seeing the city while dining, not from receiving a formal architecture lesson.

Lunch or dinner: which sailing fits you?

Lunch is the easier choice for a daytime celebration or a special meal that does not need a late finish. You get the same basic three-course structure, skyline views, DJ, and outdoor decks. The mood can still be festive, but daylight makes it easier to study the buildings and shoreline.

Dinner adds a more romantic setting, especially near sunset. The lights of downtown and the dark water create a different mood from the daytime cruise. Dinner also offers the widest menu, including lobster, steak, richer desserts, and extra seafood choices, though several of these come with added charges.

I would choose lunch if you care most about seeing the architecture clearly and keeping the outing simple. I would choose dinner if you are marking an anniversary, birthday, or date and want the cruise to feel like an evening event.

Do not assume dinner is quiet or intimate throughout. The DJ and dance floor can turn the boat into a party. That is a plus for groups and celebrations, but less appealing if you want soft conversation over a leisurely meal.

The DJ, dance floor, and onboard mood

After or between courses, you can listen to the live DJ, dance, or settle on an outdoor observation deck. The entertainment gives the cruise energy that a standard lake sightseeing trip does not have.

Several guests have enjoyed the party feel, and one birthday group found the DJ especially effective. The staff has also received strong praise, including a server named Leslie, who was described as attentive, patient, and helpful without hovering. That kind of service matters when the evening includes several moving parts, from meal timing to drinks and special occasions.

The music level is not always ideal for every table. On one sailing, the volume made conversation difficult, and children using the dance floor added to the noise. I would not book this experience expecting a hushed dinner. Choose it for a social evening with music, not for a quiet meal beside the water.

The outdoor decks are a welcome escape when you need fresh air or a break from the music. Interior areas are non-smoking. Smoking is allowed only on the outdoor observation decks.

Price and what you receive for $88

At $88 per person, the cruise costs more than a regular lunch or dinner, but you are paying for several parts at once: a three-course plated meal, a two to three-hour lake cruise, table service, skyline views, onboard entertainment, and access to the outdoor decks.

The price makes the most sense when you want a special occasion package rather than the cheapest way to see Chicago. A simple architecture cruise may be better if sightseeing is your only goal. A restaurant with a view may be better if food quality and conversation matter more than movement and entertainment.

The value improves for a birthday, anniversary, family gathering, or first visit to Chicago. You do not need to arrange a separate meal and sightseeing activity, and the setting does much of the work for a celebration.

Budget for extras. Alcoholic drinks are not included, premium menu items cost more, and souvenir photos are available for purchase. The base price includes coffee, hot tea, and iced tea, but not a full drinks package.

Dress code, comfort, and accessibility

The dress code is stricter than at most casual Chicago restaurants. Smart-casual clothing is expected, and jackets or cocktail attire are strongly suggested for dinner. Jeans, shorts, tank tops, halter-tops, T-shirts, gym shoes, sandals, and flip-flops are not allowed.

This rule can affect your plans if you are spending the day sightseeing around Navy Pier. Bring the correct clothes with you rather than assuming you can board in what you wore for walking around town.

The ship is wheelchair accessible. The experience is offered in English, and infants are free when you select the infant ticket option. The boat has interior seating, outdoor observation areas, restrooms, and a dance floor, though the overall comfort will depend on weather, crowd levels, and how much time you spend outside.

In colder months, the top deck can be chilly. A November sailing, for example, may offer fine views but make outdoor sightseeing uncomfortable. On warm, clear days, the outside decks become one of the cruise’s best features.

Who will enjoy this Chicago cruise most?

I would recommend the Odyssey to you if you want several things in one outing:

• A celebratory meal with music and a city view
• A date-night setting with a sunset or evening skyline
• A group event with a dance floor and shared table
• A first look at Chicago’s downtown skyline from the lake
• A more dressed-up experience than a standard sightseeing boat

Families can enjoy it, but the DJ, dress code, and formal meal format may not suit every child. The dance floor is part of the appeal, though a busy sailing may be noisy.

Architecture fans should know what they are getting. You will see many important buildings, but the cruise does not promise a detailed spoken tour. If the skyline itself is enough, the boat provides excellent viewing angles. If you want expert explanations of Chicago’s design history, pair this with a separate architecture tour.

Should you book the City Cruises Chicago Premier Cruise?

Book it if you want dinner with a view, a live DJ, and a special-occasion atmosphere. The combination of a plated meal, Lake Michigan skyline, outdoor decks, and dancing gives you more than a standard restaurant meal.

Skip it if you mainly want a quiet dinner, detailed architectural commentary, or the lowest-cost way to see the city. Check the departure instructions carefully, arrive at least 30 minutes early, reserve your entire group together, and dress more formally than you might expect.

For many visitors, the best choice is an evening sailing in mild weather, when you can enjoy the meal indoors and step outside to see Chicago lit up. Just remember that the skyline is the main attraction, the music can be loud, and premium food and drinks can raise the final bill.

FAQ

Where does the Odyssey Chicago cruise depart?

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

How long does the cruise last?

The cruise lasts approximately two to three hours, depending on the selected sailing and availability.

Is lunch or dinner included in the price?

Yes. The selected option includes either a three-course plated lunch or a three-course plated dinner. Menu items may change.

Are drinks included?

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?

Wear smart-casual clothing. Jackets and cocktail attire are strongly suggested for dinner. Jeans, shorts, sandals, flip-flops, sleeveless shirts, tank tops, T-shirts, and sports shoes are not permitted.

Is the cruise wheelchair accessible?

Yes, the experience is wheelchair accessible.