Built on the shore of Lake Michigan, Chicago is a great place to a take a dining cruise. This fact has been recognized and acted upon with great enthusiasm by Entertainment Cruises, which operates a few dining cruise companies in Chicago. As far as we can tell, Entertainment Cruises is also the only company that operates dining cruises in Chicago, so below we focus on detailing, in outline, what these companies offer. In other words, we have composed a guide to dining cruises in Chicago, which should direct you toward the company with which you want to book your outing on Lake Michigan.
In general, though, you needn’t really concern yourself with the exact company you book with, as the different operations that Entertainment Cruises runs can be more or less considered one unified company with a few different ships. More precisely, Spirit Cruises, Odyssey Cruises, and Mystic Blue Cruises, which are all separate entities, operate comparable dining cruises, and when you search for cruises one of these company’s sites, you are actually searching the listings of all three companies. Thus, you will likely decide which cruise to book on the basis of the details of the individual cruise, like when it is offered, not on who is offering it.
There are definitely differences between Spirit, Odyssey, and Mystic Blue’s offerings – apart from different sailing schedules, they can also have different dining options (like buffet versus plated meals) – but the point we are emphasizing is just that these companies are not in competition with one another. Spirit, Odyssey, and Mystic Blue could just as easily operate under one name. (In a sense, they do operate under one name, Entertainment Cruises, but this larger entity actually operates two additional cruise companies in Chicago – Elite Private Yachts, for private boat parties, and Seadog, used primarily for sightseeing tours.)
Between Spirit, Odyssey, and Mystic Blue, the number of dining cruises is substantial, and so it isn’t advisable or worthwhile to try to list all of the different cruises you can take. However, painting with broad strokes, there are essentially two kinds of cruises offered by the three companies. The first are regular dining cruises that center on brunch, lunch, or dinner. These cruises are offered on a consistent basis, and are clustered around the weekends, although there are several during the week as well. The other types of dining cruises are for the specialty cruises. These cruises either mark a holiday or were created by Entertainment Cruises, presumably for promotional purposes. Thus, there are things like Valentine’s Day cruises, liable to be celebrated by any given dining cruise company in the U.S., but also “Laughs on the Lakes Comedy Cruises” and “Chicago Senior Cabaret Lunch Cruises,” which exists only in the world of Entertainment Cruises.
Between the regularly scheduled brunch, lunch, and dinner cruises and the different types of specialty cruises, there are a wide range of Chicago dining cruises to choose from. However, it is worth noting that the frequency of cruises definitely starts to taper off as winter sets in, so you’ll have fewer options from roughly November through April. Still, thanks to the specialty cruises for holidays, there are even dining cruises in Chicago in the dead of winter. For more information, you can check out the Entertainment Cruises page dedicated to Chicago.