Skydeck Chicago Pie in the Sky Dining Experience

Thinking about taking your dinner plans to new heights? The Skydeck Chicago Pie in the Sky Dining Experience offers a chance to dine at one of the city’s most iconic landmarks—Willis Tower—after it closes to the public. While the idea of enjoying gourmet Chicago-style pizza with a panoramic view sounds incredible, it’s worth knowing what you’re really signing up for before booking.

One thing we love about this experience is how it transforms a typical sightseeing visit into a private, intimate moment with Chicago’s skyline as your backdrop. Plus, the opportunity to customize your deep-dish pizza with up to six toppings adds a fun, personal touch. On the flip side, some reviews highlight that the event can be a bit disorganized or not quite as luxurious as the photos might suggest.

If you’re someone who appreciates unique date ideas, celebrating special milestones, or just wants to tick off a bucket list item with a bit of exclusivity, this tour could be a good fit. But if you’re expecting top-tier fine dining or a flawless experience, keep in mind some of the reported hiccups.

Key Points

• Exclusive Access: You get to enjoy the Skydeck after hours, away from crowds.
• Customizable Menu: You can choose your pizza toppings and enjoy Chicago deep-dish at a high altitude.
• Spectacular Views: Expect breathtaking nighttime skyline views, perfect for photos.
• Limited Group Size: The experience is intimate, with only a few tables—ideal for romantic dinners or small celebrations.
• Variable Reviews: While some travelers praise the experience, others mention organizational issues or mismatched expectations.
• Price Point: At $154 per person, it’s a premium experience, but whether it’s worth it depends on what you value—views, food, or exclusivity.

What to Expect from the Skydeck Pie in the Sky Dining Experience

Imagine being 1,353 feet above Chicago, with the entire skyline unfolding beneath you. That’s what this experience promises—a luxurious, private dinner on the top floor of Willis Tower after the crowds have gone home. But what does that look like in real terms?

Getting There and Entry: The experience starts at the Skydeck Chicago address on S. Wacker Drive. You’ll receive a mobile ticket, and depending on your chosen time slot—either 7 pm or 11 pm—you’ll be escorted to the top after the usual public hours conclude. The elevator ride up is part of the fun, often accompanied by audio-visual presentations that set the mood.

The Setting: Once at the top, your table is carefully positioned to maximize the views of Chicago’s night-lit skyline, Lake Michigan, and the Chicago River. With only one or two other tables, the atmosphere is intimate, allowing for a relaxed, romantic vibe or a special celebration. The reviews highlight that some guests felt they had nearly the entire floor to themselves, which adds to the exclusivity.

The Meal: The star of the evening is the deep-dish pizza—crafted by Giordano’s—customized with your choice of toppings, from classic pepperoni to artichokes or BBQ chicken. You can specify your menu options when booking, which is nice if you have dietary preferences or want a little variety. Alongside the pizza, a fresh salad, dessert, and non-alcoholic beverages are included. The dessert options include cookies or brownies, a sweet way to wrap up.

The Experience: As you enjoy your meal, you’ll be treated to stunning views that make for memorable photos—many reviews mention how perfect this is for capturing Chicago at night. The atmosphere is described as romantic and peaceful, a far cry from the busy daytime crowds.

The Itinerary: A Closer Look

Stop 1: Skydeck Chicago – Willis Tower
Your journey begins by riding the elevator up to the Skydeck. The experience is about more than just dinner—it’s about elevating your perspective on the city. Once at the top, you’re guided to your table, which is strategically placed for the best views, often near the windows or at the edge of the floor.

Dining: You’ll sit down at your designated table, enjoy your customized deep-dish pizza, and sip on non-alcoholic drinks. The reviews reveal a mixed experience here: some describe the dinner as “great” and “delicious,” while others felt the food was just “decent.” Still, the views tend to be universally praised.

Post-meal freedom: Guests often mention that after dinner, they’re free to walk around and take photos, enjoying the exclusive use of the Skydeck space. Some reviewers appreciated having the entire floor to themselves, making the experience feel very private.

Timing: You have up to 1.5 hours for your meal, which should be enough for a relaxed pace. The experience is designed to be flexible, but note that reservations are based on availability and are not guaranteed until confirmed.

Authentic Feedback from Travelers

One of the most frequently praised aspects is the views. Several reviews call it “wonderful” and “breathtaking,” with guests remarking on how the city lights stretch out before them, creating memorable photo opportunities. A few said it was a “once-in-a-lifetime” experience, especially for celebrating milestones like anniversaries.

On the other hand, some travelers were less impressed. One review pointed out that the dinner was served in the dark, making it difficult to see the food, which diminishes the overall experience. Others felt that the event was misleading—expecting to dine in a glass box or veranda, but instead, tables were set a few meters away, which disappointed some guests expecting a more immersive dining setup. There was also mention of organizational issues, like delays in getting up to the Skydeck or confusion about the schedule.

Food quality also received mixed reviews. While some found the pizza and service quite good, others thought the offerings were “just okay” or “under par,” especially considering the cost. The inclusion of only non-alcoholic beverages was noted, so don’t expect wine or cocktails with your meal.

Pricing and Value

At $154 per person, this experience is definitely on the higher end. It’s not just about the meal—it’s about the exclusivity, the views, and the memory-making potential. For some, that’s worth the splurge, especially if celebrating a special occasion or seeking a unique date night. Several reviews celebrated the event as “romantic” or “perfect for a milestone,” which speaks to its appeal for meaningful moments.

However, some felt the price didn’t match the quality of the food or the organization. One review bluntly said it wasn’t worth it, citing the meal and the limited menu as reasons. So, if your priority is a gourmet dinner, this might fall short, but if you’re after the vibe and the scenery, it could well be worth it.

Practical Tips for Booking and Visiting

• Book in advance: On average, this tour is booked about 23 days ahead, so plan early if you want a specific date.
• Choose your time wisely: Evening slots at 7 pm or 11 pm cater to different preferences; late-night might offer a quieter atmosphere.
• Enter special requirements: Make sure to specify your pizza toppings and dietary preferences when booking.
• Arrive early for the best experience: While the experience starts at your scheduled time, arriving early might help you relax and explore the Skydeck beforehand.
• Weather matters: Since this is outdoors at the top of a skyscraper, poor weather could impact your experience; the tour is dependent on good weather conditions.
• Cancellation policy: Be aware that this experience is non-refundable and cannot be changed, so only book if you’re confident about your plans.

Who Should Consider This Tour?

This experience is best suited for romantic couples, special celebrations, or Chicago enthusiasts looking for a unique perspective on the city. If you enjoy breathtaking views and a quiet setting, you’ll love the peace and exclusivity this offers.

If you’re expecting a gourmet meal with high-end service or a completely seamless experience, keep in mind some reviews mention organizational issues and average food quality. It’s more about the overall vibe and the spectacular scenery than a culinary masterpiece.

For families or travelers seeking a hearty dinner with a lively atmosphere, this might not be the best choice. The focus is on intimacy and views, not on a bustling restaurant vibe or child-friendly options.

FAQs

Is this experience suitable for children?
While not explicitly stated, given the focus on romantic and special occasions, it’s likely geared more toward adults. The experience is intimate, and the dinner is limited to non-alcoholic beverages, but no specific age restrictions are mentioned.

How long does the dinner last?
Up to 1.5 hours, giving you ample time to enjoy your meal and take photos without feeling rushed.

Can I choose my pizza toppings?
Yes, you can select up to six toppings when booking, with options like pepperoni, mushrooms, artichokes, and more.

Is the experience weather-dependent?
Yes, since it involves outdoor viewing at the top of a skyscraper, poor weather could affect the experience. If canceled due to weather, you’ll be offered a different date or a full refund.

Are beverages included?
Yes, non-alcoholic options like Pepsi, Diet Pepsi, Sierra Mist, Mountain Dew, Mug Root Beer, and Lipton Tea are included.

Can I bring my camera or phone?
Absolutely. Guests frequently report taking great photos of Chicago at night, especially since the tables are positioned for optimal views.

What if I want to change or cancel my booking?
The experience is non-refundable and cannot be changed once booked, so plan accordingly.

Is it worth the price?
It depends on what you value: the exclusivity, the views, and the special occasion atmosphere. Some find it a memorable, unique experience, while others feel the food and organization don’t justify the cost.

What should I wear?
While not specified, casual to smart casual attire is generally appropriate for a dinner like this. Remember it’s an evening event at high altitude, so dress comfortably yet neatly.

Final Thoughts

The Pizza in the Sky experience at Willis Tower offers a blend of breathtaking vistas and a personalized dining experience above Chicago’s skyline. It’s a memorable way to celebrate a special occasion or indulge in a unique perspective of the city. The limited group size and exclusive access elevate the experience beyond a typical dinner outing, making it ideal for those seeking intimacy and spectacular views.

However, it’s not a flawless experience. Organizational hiccups, average food quality for some, and a premium price tag mean you should approach it with realistic expectations. If your main goal is a romantic night with a view and you’re okay with some imperfections, you’ll likely come away with lasting memories.

For anyone wanting to combine Chicago’s night skyline with a private meal in an iconic setting, this is a solid choice—just be sure to weigh the costs and reviews before booking.