Willis Tower Skydeck Dinner. Enjoy an unforgettable sky-high meal during this 2-hour Willis Tower dining experience at the Skydeck, an observation room situated high above Chicago's magnificent urban landscape. This 1,353-foot (412m) viewing area provides the magical setting for your evening, accompanied by a delicious Chicago-style deep-dish pizza. Best of all, this special excursion offers VIP after-hours access to the Skydeck, ensuring the ultimate setting for that special occasion. Book this Willis Tower Skydeck Dinner From $117.64.