Our Dinner on the “Top of the World”

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 Chicago Willis Tower Pie In The Sky Dinner

OK, 3rd top of the world now!  That’s right, we’re talking the Willis Tower (you may know it better as the Sears Tower…formerly the tallest building in the world) in Chicago.  I remember going to the top observation deck 12 years ago, when it was still Sears Tower.  Our youngest sister actually lost her very first tooth up there…it’s a fun family story for all of us.  So I was way excited to go again, now that they have the glass “ledge”.  That would’ve been enough excitement in itself, but did you know you can have a super romantic, (and fairly exclusive), dinner up there?! I had no idea that was a thing and jumped at the opportunity, as soon as I learned of Skydeck’s “Pie in the Sky” event.

I didn’t quite know what to expect, but I was stoked!  I knew that dinner was going to be at 11pm after it closed to the public, we would be having (Pizza) Pie for dinner, and there was a maximum of 9 tables each night.  I had a few thoughts and questions running through my mind… “I hope we get a good table close to the window!” “That would be so cool if we get to stand on the ledge too.”  “I wonder if they will put us at a table with a lot of other people.”  And all of my questions were soon to be answered…I just couldn’t wait!

You’re told to be there between 10:45-11 to check in.  We were a bit early, so waited in the lobby until 11.

After we parked, we headed to the front desk, where they checked us in, printed out our badges/pass for the night, and went through security..(just like at the airport…metal detector, and the x-ray machine for your belongings).  Then we waited in the lobby for about 20 minutes or so, until someone came to take us up.  There were only 6 of us heading up the “60 seconds to the top” elevator, to the 103rd floor.

I was sure we were headed up to meet the other group of people, but I was pleasantly surprised to see it was just us for the time being.

These were the only tables in the whole place all night!

“Go ahead, walk around, take all your pictures, and take as long as you want.”  The place was completely empty!  Ghost town up here!  We went ahead and let them show us our table first so I could put my jacket down and go enjoy the sites.  We had a table for 2.  It was going to be a nice private dinning experience.  The 2 other couples went their opposite ways, and B and I were left to ourselves.  I looked up from the table, and there we were, seated right in front of one of the 4 “ledges”.

“Wait, we can go on those?!” I couldn’t contain my excitement.  I walked to the edge and froze for a second.  “You go first!” I told B.  We stepped out and I immediately fell a tad bit dizzy as the ground disappeared and we were now standing outside the building, over the city.

Another one of the couples walked up, so I snapped some pictures of them on the ledges, and they returned the favor.

We walked around the rest of the deck, as the other 2 couples sat down.  It was so awesome, and so romantic to be at the (3rd) top of the world, seemingly by ourselves.  I was loving every minute.

We sat down and were served our salads we had ordered.  (We ordered our food a couple days prior.  3 course meal…salad, 6 topping stuffed Chicago Pizza, a drink and dessert.)  Just as they were giving us our salads, another couple walked in, for a total of 10 people in that entire floor. (the waiter and host included, who took care of all 4 tables)

Then it was time for the “Pie in the Sky”, a Giordano’s famous Chicago style pizza, and boy was it delicious!  Being that it was nearing midnight, we didn’t eat too much, but the waiter boxed it up for us to take home.  They brought out our dessert, cause there’s always room for dessert no matter how full you are!

We got up, took some more pictures (thanks for putting up with me, B!), and walked around one last time…once again, having the place to ourselves as the other couples were finishing up.  It was a beautiful, magical night.

With “Pie in the Sky”, you’re not really paying for a fancy dinner at a fancy restaurant.  You’re paying for the experience and exclusivity or it.  But if you really think about it, tickets up to the 103rd floor are $23 per adult, and you’re fighting with large crowds trying to get a picture without strangers in it. (You can pay $49 for an “Fast Pass”, to skip the lines waiting for the elevator.) And a meal like that from Giordano’s can set you back around the same as well (ours would have cost a little over $65 at the restaurant).  So, the math kind of evens out…and the fact that we had the place basically to ourselves and got to experience eating up there with the amazing views is worth the little extra money to me.

Check out all the details and get your reservations here.

**p.s. they also have breakfast in the sky, and lunch on the 99th floor, if dinner is too late for you.

Sara, a seasoned expert in wedding planning and date ideas, brings a wealth of experience to our couples blog. With a background in the television industry and hands-on involvement in a dozen weddings, including working as a wedding assistant on "My Fair Wedding with David Tutera," Sara has an innate understanding of the magic that makes weddings truly special. Growing up with four sisters has given her unique insights into the dating world, making her a go-to source for practical and heartfelt dating advice. Her knowledge and enthusiasm make her the perfect guide for couples seeking to infuse their relationships with creativity and love.

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