City Cruises Chicago: Premier Lunch or Dinner Cruise

If you’re looking for a way to combine scenic city views, good food, and a touch of elegance, this cruise on Lake Michigan might just be the perfect fit. While we haven’t personally hopped aboard, reviews indicate it’s a delightful way to experience Chicago from its shimmering waters.

One of the things we love about this experience is the spectacular panoramic views of Chicago’s iconic skyline—Navy Pier, Grant Park, and the Willis Tower all come into view in a way that’s both impressive and ideal for photos. The other standout: the gourmet 3-course meal served on board, which elevates a sightseeing trip into a proper dining event.

However, a consideration worth noting is the potential for logistical hiccups, such as last-minute changes to departure points, which some guests found frustrating. That’s a reminder to stay alert to email updates.

This cruise appeals most to travelers who appreciate a blend of scenic beauty and culinary enjoyment, especially those celebrating a special occasion or seeking a romantic evening on the water.

Key Points

• Spectacular views of Chicago’s skyline from Lake Michigan
• Gourmet 3-course meals with attentive service
• Live DJ and dance opportunities onboard
• Flexible options for lunch or dinner
• Accessible and easy to board at Navy Pier
• Price around $94 offers good value given the experience

You can check availability for your dates here:

A Closer Look at the Experience

The Odyssey Lake Michigan sets the scene for an elegant outing. The yacht itself is designed for prime viewing, with a large observation deck that offers 360-degree vistas. Whether you’re seated at your table enjoying your meal or strolling outside to take photos, the views are the star of the show.

Starting at Navy Pier, you’ll check in at the ticket booth, where staff are friendly and welcoming. The departure point is straightforward—once aboard, you’ll be greeted and offered a chance to have your photo taken, a nice touch to remember your experience. The boat’s name, Odyssey Lake Michigan, is clearly displayed, making it easy to spot.

The Menu and Dining Experience

The 3-course meal is a highlight. For starters, options range from Caesar Salad to Lobster Bisque or Jumbo Shrimp Cocktail—dishes that hint at upscale fare. Main courses include choices like Atlantic Salmon, Oven-Roasted Chicken, Braised Beef Short Ribs, and even Pan-Seared Cod. For the dinner cruise, there are premium options like Filet Mignon, USDA Prime Striploin, or Broiled Maine Lobster Tails, at an extra cost.

Desserts are equally tempting: Eli’s New York Cheesecake, Double Sorbet, or Triple Chocolate Mud Pie, among others. The carefully curated menu ensures a satisfying meal that makes the ticket price of around $94 seem like good value—especially when you consider the quality of food and ambiance.

Atmosphere and Entertainment

Once seated, the live DJ sets a lively tone—perfect for those who want to dance or simply relax and take in the scenery. The boat’s interior is elegant but comfortable, with the outdoor decks providing a more open-air experience. Many reviews note the friendly staff and attentive service, which helps elevate the overall experience.

The Views and Landmarks

As the boat cruises along Lake Michigan, you’ll enjoy panoramic views of Chicago’s skyline—a spectacle best appreciated from the water. Landmarks like Navy Pier, Grant Park, and the Willis Tower are visible, offering memorable photo opportunities. One reviewer mentions that the view of Chicago at sunset was particularly romantic.

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Additional Features and Tips

Unlimited coffee, hot tea, and iced tea are included, and alcohol is available for purchase—another reason to arrive ready for a leisurely, indulgent outing. For those celebrating a special event, the cruise can be a charming way to mark the occasion, as one guest celebrated their birthday with beautiful scenery and music.

It’s worth noting that attire should be smart casual, with jackets recommended for the dinner cruise. Avoid jeans, sandals, or shorts to maintain a polished look. Boarding begins 30 minutes prior to departure, so plan accordingly.

What Travelers Are Saying

Many reviews praise the quality of the food and the attentive service. One guest noted, “The servers and Heather were all great,” highlighting the friendly staff. Others appreciate the stunning views—a recurring theme—like Rosie who said, “Food could have been warmer, but the view of Chicago at sunset was so romantic.”

A few reviews mention logistical issues, such as last-minute changes to the departure point, which caused some confusion and inconvenience. Allan shared that a late email about the change from the lake to the river almost made him miss the cruise, emphasizing the importance of checking updates.

Overall, guests agree that the experience offers excellent value, combining great scenery, good food, and lively entertainment. Even when technical issues arose on some trips, staff responded well, often offering vouchers or alternative arrangements, which many found appreciated.

Breakdown of the Itinerary

The cruise begins at Navy Pier, a vibrant hub that’s easy to access. After check-in, you’ll board the Odyssey, where a crew member welcomes you and encourages you to take photos—an enjoyable way to start your journey.

Once seated at your table, the gourmet meal begins. The starter options are served with elegance, and the main courses are presented with care, featuring dishes prepared by an onboard chef. The live DJ begins to set the mood, and after eating, many guests choose to relax or dance.

Throughout the cruise, you’ll pass by Chicago’s most recognizable landmarks. The observation deck provides unobstructed views of skyscrapers and waterfront attractions. For those interested in photography, the water offers a different perspective on the city’s iconic architecture.

The cruise generally lasts between 2 to 3 hours, making it a perfect afternoon or evening outing. It’s designed to be a leisurely experience, allowing for plenty of time to enjoy the scenery, food, and music.

Practical Tips for Travelers

• Arrive early: Boarding begins 30 minutes before departure, so plan to get there on time.
• Dress smart-casual: Jackets and cocktail attire are recommended, especially for dinner cruises.
• Check your email: Be alert for any updates about the departure point, as last-minute changes have occurred.
• Book ahead: This experience is popular and can sell out, so reserve in advance.
• Bring your ID or passport: Required for boarding.
• Food allergies?: Inform your server beforehand—menu items are subject to change.
• Consider the weather: The outdoor decks are open air, so dress accordingly.
• Bring your camera: The views are some of the best you’ll get of Chicago.
• Accessibility: The cruise is wheelchair accessible.

The Bottom Line

If you’re eager to see Chicago from a unique vantage point while enjoying a quality meal and a lively atmosphere, this cruise hits the right notes. It’s especially well-suited for couples celebrating a special night, families wanting a scenic outing, or anyone looking to combine sightseeing with fine dining.

The experience’s value is strong, given the scenic views, good food, and entertainment, all in a comfortable setting. While some logistical hiccups can occur, the staff’s professionalism and the overall atmosphere tend to leave a positive impression.

For travelers who want a bit of everything—great scenery, delicious cuisine, and a touch of celebration—this cruise on Lake Michigan delivers. Just remember to keep an eye on your email, dress smart, and prepare to relax and enjoy one of Chicago’s most memorable waterfront experiences.

FAQ

How long does the cruise last?
Most cruises are between 2 and 3 hours, offering plenty of time for sightseeing, dining, and relaxing.

Where does the cruise depart from?
It departs from Navy Pier, with check-in at the Odyssey Lake Michigan ticket booth near the Shakespeare Theatre sign.

Is there a dress code?
Yes, smart casual is recommended, with jackets and cocktail attire suggested for the dinner cruise. Avoid jeans, shorts, and flip-flops.

Can I purchase alcohol on board?
Yes, alcoholic drinks are available for purchase, along with unlimited coffee, hot tea, and iced tea.

What food options are available?
A gourmet 3-course meal is served, with choices ranging from salads and seafood to premium steaks and lobster tails for dinner.

Are there vegetarian options?
While not explicitly stated, the menu includes various dishes; it’s best to inform the crew of any dietary restrictions at booking or check-in.

Is the cruise accessible for wheelchair users?
Yes, the cruise is wheelchair accessible, making it suitable for guests with mobility needs.

What should I do if I have a food allergy?
Inform your server before ordering so they can advise on menu options suitable for your allergies.

How do I know if the departure point has changed?
Check your email for updates, especially if you receive last-minute notices; some reviews mention last-minute location changes causing confusion.

This experience offers a memorable way to view Chicago’s skyline, enjoy an excellent meal, and dance or relax to live music—all in about 2-3 hours of your time. Perfect for a special occasion or just a fun night out, it combines the best of sightseeing and dining on Lake Michigan.

You can check availability for your dates here: More Great Tours Nearby