Go to ChooseChicago.com, Chicago's Convention and Tourism Bureau website. Navigate to the "Tours & Attractions" listings. From there, narrow your search to "Boat Tours."
Visit the website of the Chicago Office of Tourism at ExploreChicago.org. The tourism office website lists Chicago's three main dinner cruise lines, along with their contact information. Discounted tickets are frequently available through the website.
Notify local travel agents that you will be visiting the area, and are looking to purchase discounted dinner cruise tickets. Agents who work specifically with Chicago attractions should be familiar with the various dinner cruises, know which ones are recommended and how to get the best deals.
Plan the dinner cruise in the off-season. Summertime is the tourism high point, and cruise lines can afford to charge full price for their services. Likewise, special holiday dinner cruises, such as Christmas or New Year's (when the weather allows), will be more expensive. You can usually find the best deals when the lines first open in spring, or in fall, when tourism slows down.
Call a cruise line and see if they have any last-minute guest discounts. If the cruise is not completely booked, the cruise line may choose to offer a discount rather than lose the customer.