Skydeck Chicago Pie in the Sky Dining Experience

Experience Chicago's skyline from 1,353 feet up with a private, after-hours dinner at Skydeck Willis Tower, featuring deep-dish pizza and stunning views.

Skydeck Chicago Pie in the Sky Dining Experience: An In-Depth Review

Skydeck Chicago Pie in the Sky Dining Experience - Skydeck Chicago Pie in the Sky Dining Experience: An In-Depth Review

Imagine having the Chicago skyline all to yourself, high above the city’s bustling streets, with a delicious slice of deep-dish pizza in hand. That’s exactly what this Skydeck Chicago Pie in the Sky Dining Experience promises — a private, after-hours dinner at Willis Tower’s Skydeck, offering breathtaking views that are hard to beat. It’s a unique way to enjoy the city’s iconic architecture, especially suited for special occasions or a memorable night out.

We’re not claiming to have personally tasted this experience, but from what seasoned travelers and reviews tell us, it offers a blend of spectacular vistas, good food, and intimate atmosphere. Two highlights stand out: the exclusive access after the crowds leave, and the customizable deep-dish pizza that makes Chicago famous.

On the flip side, some travelers find the price tag steep for what’s essentially a meal and a view, and a few mention logistical hiccups at check-in. Nevertheless, this experience seems best suited for those celebrating a special milestone, or anyone craving an unstoppable sunset or night view from one of the tallest buildings in the world. If you’re prepared for a controlled environment with limited group size, this might be just the ticket.

Key Points

  • Unbeatable skyline views from 1,353 feet high, available exclusively after hours
  • Customized deep-dish pizza with up to six toppings, plus salad and dessert options
  • Ideal for celebrating special occasions like anniversaries or birthdays
  • Limited group sizes keep the experience intimate, with only up to 7 tables at a time
  • Booking well in advance is recommended, with an average of 22 days ahead
  • Non-refundable policy applies; weather cancellations are the only exception

What is the Skydeck Pie in the Sky Dining Experience?

Skydeck Chicago Pie in the Sky Dining Experience - What is the Skydeck Pie in the Sky Dining Experience?

This is a two-hour, VIP-style dinner at the Skydeck Chicago, situated over 1,300 feet above the city in the Willis Tower. The experience begins with a private elevator ride up to the top of the skyscraper, where you’ll enjoy after-hours access to the Skydeck, which is normally open to the public during daylight hours.

Once you arrive, your table is set with spectacular panoramic views of Chicago’s skyline, Lake Michigan, and the Chicago River. The atmosphere is designed to feel exclusive and intimate, perfect for romantic evenings, birthday celebrations, or special milestones. It’s not just about the food; it’s about seeing the city from a vantage point few get to experience.

The Itinerary: An Hour-by-Hour Breakdown

Ride to the Top: The journey begins with a fast, glass-enclosed elevator ride that whisks you up to the 103rd floor. During this ascent, most reviews mention an audio/video presentation that adds a bit of context and heightens anticipation. The elevator ride itself is part of the thrill, offering a glimpse of the towering structure.

Exclusive Access: Once at the top, your group is shown to a private dining area. Unlike the daytime crowds, you’ll have the place to yourself, with windows wrapping around for 360-degree views. This means perfect photo opportunities and a sense of being on top of the world.

Dining: Your meal is catered by Giordano’s Pizza, famous for its stuffed deep-dish. You can select up to six toppings, with options like bacon, sausage, mushrooms, green peppers, jalapenos, and more. The menu also includes a salad, dessert (brownie bites or cookies), and non-alcoholic beverages such as Pepsi or Lipton Tea.

Duration: You have about 1.5 hours to enjoy your meal, with the entire experience lasting approximately two hours. During this time, you can relish breathtaking views, good company, and a relaxed atmosphere.

Authentic Traveler Insights

Some reviews highlight the smooth organization and attentive service, describing it as “well planned” and “a great way to experience the city in a unique setting.” Others note the privacy and quiet, which is a real plus if you’re celebrating a special occasion.

However, not all feedback is glowing. A few mention initial check-in delays or feeling somewhat rushed during their meal, especially if the timing is tight. One reviewer expressed disappointment, saying, “For $300, the menu and food could have been way better,” noting that the experience is mostly about the view rather than the meal itself.

The Food: Is It Worth It?

The deep-dish pizza is the star here, with many enjoying the customizable toppings and authentic Chicago flavor. The salad options cater to different tastes, and dessert provides a sweet finish. But some travelers feel that the food quality is just okay for the price, emphasizing that the main draw is the view and exclusivity rather than gourmet dining.

Who Will Love This Experience?

Skydeck Chicago Pie in the Sky Dining Experience - Who Will Love This Experience?

This dinner experience is most appealing for romantic couples, families celebrating milestones, or groups seeking a private, scenic dinner. If you’re after Instagram-worthy photos, a special night in Chicago, and no crowds, this is a prime choice. It’s especially suitable for those willing to pay for the privilege of a private skyline view.

That said, if you’re on a tight budget or prefer a more casual or gourmet-focused meal, you might find this experience somewhat limited. Also, if you’re expecting a full-service fine dining experience, remember that the menu is quite simple, with pizza and basic desserts.

Practical Details for Travelers

Skydeck Chicago Pie in the Sky Dining Experience - Practical Details for Travelers

  • Price: $154 per person, which includes your meal and exclusive access. While not cheap, this price reflects the premium experience and views.
  • Booking: Most travelers book about 3 weeks in advance, so plan ahead, especially for popular dates.
  • Duration: Around 2 hours, giving ample time to relax, take photos, and enjoy your meal.
  • Timing: Two seating options are available, allowing you to choose the sunset or night views.
  • Accessibility: Near public transportation, making it easy to reach without a car.
  • Group Size: Limited to 7 tables at a time, ensuring a more intimate atmosphere.
  • Weather: The experience is weather-dependent; if canceled due to poor weather, you’ll be offered a different date or a refund.
  • Non-Refundable: Keep in mind, this is a non-refundable experience, so double-check your plans.

Authentic Traveler Feedback

Skydeck Chicago Pie in the Sky Dining Experience - Authentic Traveler Feedback

Positive reviews highlight the stunning night views and romantic ambiance. One traveler shared, “The view was absolutely amazing,” while another called it “a once-in-a-lifetime experience.” Many appreciate the low crowd levels and personalized service.

Constructive comments point out occasional check-in delays, and some feel that the food is just decent for the price. As one reviewer put it, “Experience is nice, but not worth the price at all,” citing that the meal is fairly simple and that the main draw is the view and exclusivity.

Final Thoughts

Skydeck Chicago Pie in the Sky Dining Experience - Final Thoughts

This Skydeck Chicago dinner is a special way to see the city’s skyline from a vantage point few experience. The private after-hours access, combined with delicious deep-dish pizza and the breathtaking backdrop, creates a memorable outing. While the price might be steep for some, many find the value in the exclusivity, stunning views, and romantic setting.

If you’re celebrating a milestone, craving a unique Chicago experience, or simply want a quiet night above the city lights, this tour delivers. Just remember, it’s as much about the impression and atmosphere as it is about the meal.

For travelers looking for a memorable, scenic, and intimate experience at a world-famous skyscraper, the Skydeck Pie in the Sky Dining is worth considering—but be prepared for a somewhat simple menu and a premium price.

FAQ

Skydeck Chicago Pie in the Sky Dining Experience - FAQ

Is this experience suitable for all ages?
Yes, most travelers can participate, but it’s best suited for those comfortable with heights and spending about 2 hours at the top of a skyscraper.

How many people are in each group?
Up to 7 tables are available at a time, making it a relatively small, private experience.

Can I choose different meal options?
Yes, you can enter your menu choices, including up to six pizza toppings, salad, and dessert options, when booking.

What if the weather is poor?
The experience is weather-dependent. If canceled due to bad weather, you’ll be offered a different date or a full refund.

How far in advance should I book?
Most bookings are made around 22 days in advance; early booking is recommended to secure your preferred time.

Is the experience refundable?
No, it’s non-refundable, so plan carefully.

Can I get alcohol during the dinner?
No, non-alcoholic beverages are included; alcohol is not available as part of this experience.

How long do I have to finish my meal?
You have about 1.5 hours to enjoy your dinner once seated, within the total duration of approximately 2 hours.

To sum it up, whether you’re celebrating a special occasion or seeking a night of unforgettable views, the Skydeck Pie in the Sky Dining Experience offers an intimate, scenic, and uniquely Chicago way to enjoy the city’s skyline. It’s not perfect or cheap, but for those who value exclusivity and spectacular vistas, it could very well be a highlight of your trip.