Chicago Weekend Fun!

The Odyssey Boat where we went for a Dinner Cruise in Chicago

The Odyssey Dinner Boat Cruises on Lake Michigan in Chicago are well known for providing an elegant evening on the lake with a spectacular view of the city of Chicago. When we got a chance to take one this weekend and have a night out we jumped at the chance. My fiance and I couldn’t remember the last time we had been out on a date night since we got engaged. The Chicago Odyssey Dinner Cruise was just what we needed among the crazy wedding planning we are managing right now. Here is a review of our experiences on the Odyssey Dinner Cruise this past Saturday night in Chicago.

Boarding Time: 6:30 pm

Cruise Starts: 7:30 pm

Dinner: 8PM

Jazz Music/Dancing: throughout

View of Chicago: the entire night until 10:30 pm when we got back to Navy Pier in Chicago.

Cost:  Saturday Night Dinner Cruises start at $92. This may seem like a lot of money, but there are many restaurants in the city that cost a lot more than that and don’t provide this kind of unique experience.

The weather started out rainy so we were not sure we would have much of a view on the Chicago Odyssey Cruise ship that evening, but we drove to Navy Pier anyway in hopes of a romantic evening away from everything stressful happening right now. We read that the dress code was somewhat formal and Steve actually pulled out a suit jacket to wear. The location was easy to find, we parked in the Navy Pier garage and the Chicago Odyssey Boat was docked right on the other side of the pier from where we parked by the #5 doors.  The cruise ship looked just like the pictures, big white modern looking boat with black windows. 

The rain was disappointing but when you are on a large boat for 800 people you don’t even know it’s raining outside. The interior was surprising, no communal tables or big buffets. The level we were set up on was a very elegant restaurant setting with individual tables and we sat right by the window to see the view perfectly. The meal was a 4 course meal which was very good. The appetizers, salad, main course and desert were all very good. The chicken I had as the main course was a bit heavy but Steve really enjoyed his steak and the cobbler for desert was amazing. I don’t think that people view the Odyssey or any of the Chicago Skyline Cruises as a big floating four star full service restaurant, but they really are.

The cruise started out with a champagne cocktail hour while people were boarding. Then we switched to diet pepsi so we would stay awake since we live sleep deprived lives at this point. The coffee later in the evening was also a welcome perk of caffeine. There was a full bar available though with all the amenities you would expect from a restaurant of this caliber.

The Chicago Odyssey Boat Tour Cruise also had a very nice 3 piece jazz band playing sets on the boat during the entire time we were there. They covered everything from smooth jazz to classic Sinatra standards and finished out the evening with an energetic rendition of Sweet Home Chicago. I think they are wise to have good quality music on a cruise of Chicago’s skyline. People in Chicago know their music and jazz and the couple next to us was commenting how the music was genuine jazz played well.

Our server was very attentive and the service all around was very good the entire time we were on the ship. We were still invited to go upstairs and view the skyline from the top deck of the ship even in the poor weather and the server even offered an umbrella if we needed it. I think having separate levels and rooms on this ship is a key to it’s success. There was a college honor society party on the 2nd level and a high school party on the 3rd and we never really came in contact with any of the immaturity you would expect from those younger crowds during the trip. I am sure that all the couples that were in that dining room were happy to be in a separate room also. 

We were surprised at the variety of events that people were celebrating on the Odyssey Cruise Ship that night. They make a special effort to find out what event you are celebrating and make it special. They announced people’s anniversaries and birthdays as well as had special birthday desert cakes with candles. They try and go out of the way to make your 3 hours on the lake a special and memorable experience.

We found that the Odyssey Ships don’t go far from the shore on to Lake Michigan (which is nice for the view), they initially turned south to view the city and then looped back north a few times cycling back and forth from the museum campus to Navy Pier. We did go up on the top deck and saw a beautiful view of Chicago (under a light fog) and of Navy Pier. Some HS kids were smoking up there but were just hanging out.

I can imagine how cool it must be for a high school or college student to take a date, or have a dance on Lake Michigan on a boat like this, especially if you’re from the suburbs.  It is like their first night out as adults and most of the kids looked like they took it pretty seriously. The rest of the crowd seemed like they were a mix of young couples celebrating birthdays and mid-aged people on anniversaries. One group was a girls night out all the way from Tennessee. I could see this as a great way for people traveling from other cities to really get to see Chicago and have an elegant dinner at the same time. I can also see the appeal for couples with kids to get away for the evening and go on a cruise like this just to relax and enjoy each-other’s company.

My overall experience surpassed my expectations on the Chicago Odyssey Dinner Cruise on Lake Michigan andI can confidently recommend the experience for anyone looking for an elegant night out in Chicago or someone looking for tourist suggestions for enjoying a vacation in Chicago. The spring-summer-fall seasons are probably better weather than the first week in March but it is possible to go on these scenic dinner cruises almost any time of year and we’re glad we got to get away this weekend regardless of the weather.

Have you had an experience on an Odyssey Dinner Cruise that you would like to share? Comment below…