Chicago: Skydeck Ticket and Deep Dish Pizza Dinner

Walking into the world-famous Skydeck in Chicago offers a thrill for any visitor eager to see the city from above. This tour combines that sky-high perspective with a rare chance to dine on some of Chicago’s most iconic pizza—Giordano’s deep-dish—all wrapped into a two-hour experience that promises stunning views and a taste of local comfort food. It’s a unique blend of sightseeing and indulgence that appeals to those who love a little luxury with their sightseeing.

What we really like about this experience is how it elevates the typical observation deck visit. You’re not just looking out through glass; you’re seated at a private table with a panoramic view that’s hard to beat. Plus, the small group size—with only 7 tables per evening—means you get an intimate, VIP feeling, far removed from the crowds.

A possible consideration is that this experience is only available on Thursday and Friday evenings at 9:30 pm. That limited timing might not fit every traveler’s schedule, so planning ahead is essential. Still, if you’re after a memorable night in Chicago that combines spectacular city views with delicious food, this tour deserves a spot on your list.

This tour is perfect for couples celebrating a special occasion, friends wanting a fun night out, or anyone eager to see Chicago from a different perspective. If you love viewing cities at night or enjoy classic Chicago cuisine, this experience offers a memorable mix.

Key Points

• Exclusive Setting: Only 7 tables per evening, ensuring a private, VIP experience.
• Spectacular Views: Dine on the 99th or 103rd floor, offering panoramic vistas of Chicago’s skyline at night.
• Authentic Food: Enjoy a 3-course meal featuring the city’s iconic deep-dish pizza from Giordano’s.
• Limited Availability: Offered only on Thursday and Friday nights at 9:30 pm, so booking early is a must.
• Accessibility: The activity is wheelchair accessible, making it inclusive.
• Non-Refundable Policy: Be sure about your plans, as tickets cannot be canceled for refunds.

You can check availability for your dates here:

The Experience in Detail

Arrival and Check-in

Your adventure begins at the entrance on S. Wacker Blvd, situated between W. Jackson St. and W. Adams St. This central location is easy to find if you’re exploring downtown Chicago. Upon arrival, you’ll go through security screening before heading inside to the ticket handler, who will scan your voucher. The process is straightforward, and staff are generally helpful in guiding you to the next steps.

The Skydeck Atmosphere

Once inside, you’re likely to feel a sense of anticipation—the Skydeck is an icon of Chicago’s skyline. For this experience, you’ll be led to a reserved table on either the 99th or 103rd floor, depending on availability. The setting is designed for a more intimate experience, as only 7 tables are available per evening. This exclusivity offers a quiet moment away from the day-trippers and crowds, especially at night when the city lights sparkle.

Dining with a View

What makes this experience stand out is dining at a height of 1,353 feet while gazing out over the city. You’ll enjoy a three-course meal curated by Giordano’s, a local legend known for its Chicago-style deep-dish pizza. The menu is designed to give you a taste of genuine Chicago comfort food, perfectly suited for sharing with someone special or celebrating a memorable occasion.

The meal is served in a relaxed, elegant setting—though the focus is on the view, not fine dining. As one reviewer put it, the pizza was delicious, with one guest noting they could have opted for less, but appreciated the thoughtful gesture of having leftovers boxed to take away.

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The Views

From your table, you can look out over Chicago’s iconic skyline—the Lake Michigan shoreline, the Chicago River, and the city lights illuminating the night sky. The views are often described as stunning, especially in the evening when the city is lit up. During the reviews, guests mentioned how special it was to have the entire space to themselves, allowing for unobstructed vistas and a more personal experience.

The Service and Atmosphere

Guests consistently praise the staff for their knowledgeable, attentive service. Jessica from Germany shared her appreciation for the superlieb (super kind) service, emphasizing how memorable and personal the experience felt. Beverley from the UK enjoyed having the whole place to themselves—a rare treat that added to the exclusivity and romance of the night.

Timing and Duration

The experience lasts about two hours, leaving plenty of time to savor your meal and admire the views. The timing is carefully scheduled, with the last available booking starting at 9:30 pm, ensuring you get the full effect of Chicago’s nightscape.

Why This Tour Offers Great Value

While this experience isn’t the cheapest way to see Chicago, it delivers in several ways. The private, VIP setting coupled with a delicious meal on one of the tallest buildings in the city adds a level of exclusivity and comfort that many standard observation deck visits can’t match. For travelers seeking a romantic evening, a special celebration, or simply a different way to experience the city, it’s a well worth considering.

The combination of breathtaking views and authentic food makes this a memorable highlight, especially if you’re a fan of Chicago’s culinary staples. The small group size and limited tables enhance the feeling of intimacy, making it ideal for couples or small groups.

Who Should Consider This Experience?

If you love cityscapes at night or want to enjoy a private dinner while overlooking one of America’s most vibrant skylines, this tour is a perfect fit. It’s especially suited to those looking for a romantic outing or a unique celebration experience. The ease of access and wheelchair-friendly features also make it a good choice for travelers with mobility needs.

However, if you prefer flexible scheduling or are on a tight budget, this might not be the best fit. Due to its limited availability and non-refundable policy, it’s best suited for travelers who can commit in advance and want a guaranteed memorable evening.

Final Thoughts

This Skydeck experience offers much more than just a view—it’s a carefully curated moment of luxury, intimacy, and authentic Chicago flavor. The chance to enjoy delicious deep-dish pizza in a private setting high above the city is a rare treat, and the stunning night vistas make it worthwhile.

For those who appreciate well-organized, exclusive experiences that combine spectacular scenery with regional cuisine, this tour hits the mark. It’s especially compelling for romantic couples, special celebrations, or anyone craving a different perspective on Chicago’s skyline.

While the experience’s limited timing and non-refundable policy require some planning, the value of the views and the food make it a worthwhile investment for memory-making in the Windy City.

FAQ

What is the duration of this experience?
The experience lasts approximately 2 hours, giving plenty of time to enjoy your meal and the views without feeling rushed.

On which nights is this experience available?
It’s available only on Thursday and Friday evenings at 9:30 pm, so plan accordingly.

How many tables are available each evening?
There are a maximum of 7 tables per night, ensuring a private, VIP atmosphere.

Is the experience accessible for wheelchair users?
Yes, the activity is wheelchair accessible, making it inclusive for travelers with mobility needs.

What is included in the meal?
You’ll receive a 3-course meal from Giordano’s Pizza, featuring their famous deep-dish pizza as the main course.

Can I choose where to sit?
You can select from three different table options: Ledge, Lake Michigan, or Chicago River tables, subject to availability.

Is this a good experience for a special occasion?
Absolutely, the exclusive setting and stunning views make it ideal for romantic dates, anniversaries, or special celebrations.

How do I get my tickets?
Once your booking is confirmed, you’ll receive a voucher that you can present at the entrance. The process is straightforward.

What should I wear?
Casual but neat attire is appropriate. Since it’s an evening event, bring layers if you tend to get cold.

Is the price reasonable for what I get?
While it’s a premium experience, the combination of private dining, panoramic views, and authentic Chicago pizza offers good value for those seeking a memorable night.

This tour is a smart choice for anyone looking to combine spectacular city views with authentic Chicago cuisine in an intimate setting. It’s a chance to see the city’s skyline from a whole new angle while enjoying the comfort of a private, well-served meal. If you’re planning a special night out in Chicago, this experience offers a fine mix of luxury, local flavor, and unforgettable vistas.

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