Chicago: Skydeck Ticket and Deep Dish Pizza Dinner

Imagine savoring a classic Chicago-style deep-dish pizza while perched high above the city on the 99th or 103rd floor of the Willis Tower, otherwise known as Skydeck Chicago. This is exactly what this exclusive tour offers—a two-hour, intimate dining experience that combines breathtaking city vistas with Hollywood-level privacy. Priced reasonably for such a unique experience, it’s perfect for those celebrating a special occasion or simply wanting to see Chicago from a new perspective, away from the crowds.

What we love most about this experience is the exclusivity—only seven tables are available per evening, which means you get a genuine VIP treatment. The second standout is the spectacular views of the skyline, especially at night when the lights sparkle across Lake Michigan and the cityscape. The delicious Giordano’s pizza makes it even better, offering a taste of Chicago that’s as iconic as the view itself.

On the flip side, considering the limited availability—just Thursday and Friday evenings at 9:30 pm—you’ll need to plan ahead, and it’s non-refundable once booked. For anyone who’s comfortable with that, this experience is tailor-made for travelers seeking a blend of refinement, fun, and authentic Chicago flavor. It’s especially appealing for couples, small groups, or anyone wanting an unforgettable dinner at a landmark location.

Key Points

• Exclusive VIP atmosphere with only seven tables per evening.
• Unparalleled views of Chicago’s skyline, especially at night.
• Gourmet pizza dinner from Chicago’s beloved Giordano’s, served as a 3-course meal.
• Flexible table options like the Ledge, Lake Michigan, or Chicago River views.
• Accessible and convenient location at the Skydeck entrance on S. Wacker Blvd.
• Ideal for special occasions like romantic dates or small celebrations.

You can check availability for your dates here:

A Detailed Look at the Skydeck Deep-Dish Dinner Experience

What Makes This Experience Special?

This isn’t your typical tourist outing. The opportunity to dine high above Chicago on the 99th or 103rd floor of the Willis Tower gives you a chance to see the city from a perspective few get to enjoy. The Skydeck itself is famous worldwide, but having dinner there transforms it into a personal rendezvous with Chicago’s skyline.

How It Works and What to Expect

You start by arriving at the Skydeck, located on S. Wacker Blvd, between W. Jackson and W. Adams Streets. Inside, you go through a quick security screening—nothing out of the ordinary—and then proceed to the ticket handler. After confirming your reservation, you’re led to your private table, which could be one of three choices: the Ledge with views of the city’s edge, the Lake Michigan table offering water vistas, or the Chicago River table providing a river-centric outlook.

The entire experience lasts roughly two hours, starting at 9:30 pm on your selected night. With a maximum of seven tables per evening, the setting feels intimate, almost like having your own rooftop restaurant. The staff are attentive and friendly, making sure your experience is relaxed and enjoyable.

The Meal: Giordano’s Deep-Dish Pizza

The highlight of the meal is undoubtedly the 3-course dinner featuring Giordano’s famous deep-dish pizza. The menu includes appetizers, main course, and dessert—though the specifics aren’t detailed, you can expect hearty, comforting dishes that showcase Chicago’s pizza legacy. Guests have praised the pizza’s quality, describing it as “delicious” and “authentic,” with one reviewer noting they could have managed with half the amount, but appreciated the boxed leftovers.

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The Views: Why They Matter

What truly sets this tour apart are the views. You’ll see Chicago’s skyline lit up at night, with shimmering reflections over Lake Michigan and the illuminated city streets. Jessica from Germany called it a “grand evening,” emphasizing the privacy and stunning views she experienced after hours—something that’s rare on busy daytime visits.

Beverley from the UK highlighted how “stunning the views of Chicago in every direction” were, especially when the city was all lit up. For many travelers, these perspectives provide more than just a photo opportunity—they offer a moment of genuine awe and connection with the city.

Is It Worth the Price?

While the cost isn’t explicitly listed here, considering the exclusivity and the setting, it’s quite reasonable. Paying for a private, high-altitude dinner with breathtaking views and quality pizza packs a lot of value—especially when you consider the memorable nature of the experience. It’s a perfect splurge for those wanting to elevate their Chicago trip with a dash of luxury.

Who Is This Experience Best For?

This tour suits travelers who enjoy unique, intimate experiences and want to combine sightseeing with fine dining. It’s ideal for romantic couples, small groups celebrating birthdays, or anyone craving a quiet, elevated meal with a view. Since it’s only available on select nights and limited to a small group, it’s best to book well in advance.

Additional Practical Details

• Meeting Point: The Skydeck entrance on S. Wacker Blvd.
• Duration: About 2 hours, starting at 9:30 pm.
• Accessibility: Wheelchair accessible, making it suitable for most guests.
• Reservation policy: Non-refundable, so plan accordingly.
• Availability: Exclusive to Thursday and Friday evenings.
• Group size: Limited to 7 tables per night, ensuring privacy and personalized service.
• Language: Service is generally provided in English, and the activity is non-refundable.

Authentic Reviews from Guests

Jessica from Germany mentioned it was “a unique experience” to visit after hours, with the super attentive service making her feel like a VIP. Beverley from the UK appreciated that “we had the whole place to ourselves,” and loved how the views lit up the night sky.

Other guests appreciated the delicious pizza and the stunning panoramic views, which made for a memorable and romantic evening. The small group size and quiet setting are often highlighted as major perks.

Final Thoughts: Who Will Love This Tour?

For anyone who has ever dreamed of dining in the clouds, this experience delivers on that fantasy with a dose of genuine Chicago charm. It’s best suited for travelers seeking something more personal and special than a typical skyline view—whether it’s celebrating an anniversary, impressing a date, or just indulging in a little luxury. The combination of spectacular vistas, excellent pizza, and intimate service makes it a one-of-a-kind activity that’s well worth the price for those who value memorable moments and authentic local flavors.

If you’re after a hidden gem that offers more than just sightseeing—something that elevates your trip both literally and figuratively—this Skydeck dinner might just be your perfect choice.

FAQ

Can I choose my table view?
Yes, you can select from three table options: the Ledge, Lake Michigan, or Chicago River.

Is the experience suitable for wheelchair users?
Absolutely. The tour is wheelchair accessible.

What nights is this experience available?
It is offered exclusively on Thursday and Friday evenings at 9:30 pm.

How long does the experience last?
The entire experience takes about two hours.

Is this a private experience?
It’s very intimate, with just seven tables available per night, ensuring privacy.

Can I get a refund if I cancel?
No, the activity is non-refundable once booked.

Is the pizza from Giordano’s authentic Chicago-style deep dish?
Yes, Giordano’s is a Chicago classic, famous for its deep-dish pizza.

Will I see the city lit up at night?
Yes, the views at night are spectacular, with the skyline illuminated across multiple horizons.

Is this activity good for couples?
Definitely. Many reviews mention it as a perfect romantic setting.

How do I get there?
The entrance is on S. Wacker Blvd, and you’ll proceed through security before heading to your private table.

This carefully curated experience blends spectacular views, fine food, and exclusivity, promising an unforgettable evening for anyone eager to see Chicago from a truly unique vantage point.

You can check availability for your dates here: More Great Tours Nearby