The Deal Mommy

Pie in the Sky Review: The Best Place to Eat in Chicago Is Not a Restaurant

Today I want to give a shout-out to an off-the-radar event in Chicago. I know many of you visit the Windy City for one frequent flyer conference or another.  However, you will want to take time out for Pie in the Sky. It’s the best place to eat in Chicago, and it’s not even a restaurant.

The Willis Tower Skydeck is the setting of the best place to eat in Chicago.

Pie in the Sky features private dining on top of the Willis Tower.

Most people know about the Skydeck on top of the Willis, formerly Sears, Tower. It features a jaw-dropping view of Chicago from 103 floors up and walk-out ledges so you can virtually step onto the ground below you. The Skydeck is famous and therefore becomes packed during opening hours.

What if I told you that instead of waiting two to four hours in the general admission line you could enjoy a private two hour visit? 

Pie in the Sky?

What people may not know is that the Skydeck offers Pie in the Sky, which is Giordano’s deep dish pizza (pie) served at a private table in the Sky (deck). The dining options hide on the Skydeck’s website so most tourists have no idea this is even possible. I reached out to the Skydeck and they invited Deal Girl and me to review the experience. 

The $100 per person price tag for dinner may seem steep, but I actually think it’s great value. Consider that Fastpass admission to the Willis Tower is $49 and even general admission is $23. Neither experience can compare to the absolute VIP service of visiting after hours. 

The three course meal includes a generous salad, Giordano’s famous deep dish with up to five toppings, either tiramisu or cannoli for dessert, and soda. You need to order three days before visiting as the meal is catered and delivered. 

One thing that makes Pie in the Sky unique is that it’s not only a great venue, it’s great food. Many such offerings, such as Breakfast at the Vatican, offer standard fare at a premium price in a unique setting. Pie in the Sky takes what already is a memorable meal up a substantial notch. 

Seatings are limited to nine tables, but the evening we visited only three groups dined: two families of six and me and Deal Girl. Each table stood out over one of the Skydeck glass lookouts, which meant we got fun photos like this one.

The best place to eat in Chicago is not a restaurant. It's Pie in the Sky at the Willis Tower.

And this one.

The Skydeck is the setting for the best place to eat in Chicago.

You can also do breakfast or lunch, but to me dinner is the show-stopper. During October-February dinner starts at 8:30. The rest of the year it’s a later start but is worth the next day sleep-in.

Have you tried Pie in the Sky? I’d love to hear about your visit. 

The Deal Mommy is a proud member of the Saverocity network. 

Pie in the Sky is the best place to eat in Chicago. Get in on the secret!

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