Our 30th birthday dinner: Pie in the Sky, Skydeck Chicago

My family and I are increasingly steering towards presents that are experiences, rather than things these days. It seems like we’re not the only ones; lots of people I speak to are decluttering, have just decluttered or keep saying they’re going to start so the last thing I want to do is buy them more junk that they’ll feel honour bound to keep for an arbitrary amount of time and then declutter along with the rest of it.

That’s a rather roundabout way of saying that S and I both turned 30 this year, and when our families asked us what we’d like, our minds went to experiences. My mind went to food, specifically. Previously, whilst researching activities for our Big Trip, I’d seen mentioned that you could get great views of the city from Skydeck Chicago, otherwise known as the 103rd floor of the Willis Tower (aka the Sears Tower). Whilst having a poke around their website, I came across their Pie in the Sky offer. Turns out, you can eat a meal of your choosing right in front of the Ledge, a series of glass boxes which extend out 4.3 feet from the Skydeck. 103 floors up.


Now if that’s not an experience to mark a new decade, I don’t know what is.

So we booked ourselves in.

What we didn’t realise at the time of booking (eg I didn’t read the fairly large print) was that reservations during the summer are for 11pm. Yes, on our second day in the city we had to stay up for dinner until the equivalent of 5am UK time. Needless to say, we were quite tired by the time we rolled up to the side entrance of the Willis Tower, at 10.50pm exactly.

We were amused by the strict security procedures upon arrival – we showed our passports, we went through scanners, had our bags checked, and we were definitely not allowed to take photos. We watched in amusement as one of our fellow diners had the single cupcake he’d brought passed through the x-ray scanner…


Having checked in, and feeling like we’d arrived for an international flight and not just dinner, a staff member arrived to escort us and the other four couples also eating pie in the sky up to our dining venue. Our names were checked again, as we walked a sneaky back route through the building, circumventing the spaces reserved for the queues of people who make their way up to the Skydeck during the day. Up in the lift we went, and shortly appeared at the 103rd floor.

This is the view that greeted us.


We were told we were free to wander around as much as we wanted, could take as many photos as we wanted, and generally take our time to enjoy the space. Given there were only four other couples with us, you could easily pretend you had the whole place to yourself.

We walked around the Skydeck, taking in the views, trying to spot the landmarks we’d seen earlier in the day. We saw the Chicago skyline from above.


We saw Ferris Bueller. We saw our hotel. Then we saw the Ledge.

Walking out onto a glass ledge 103 floors up is a little harder than I thought it would be. I’m not normally worried by heights but there’s just something so unnatural about stepping off the side of a building.

Still, I found that by looking straight ahead I could manage it. S wasn’t quite so sure about the whole thing so he just took photos of me, instead.


I have to say, looking down at the pavement 1,353 feet below me is something that will stay with me for quite some time.

We’d seen the ledges poking out of the side of the Willis Tower on our architecture cruise earlier in the day, and they looked impossibly high up. Standing in one looking back down at the city was quite incredible.


I was so entranced by all the shiny strings of lights laid out below us that I completely forgot we were actually there to eat.

So when our food arrived, I reluctantly dragged myself away from the view. The gluten free options were limited, so I had a plain salad to start, followed by the gluten free version of Giordano’s Pizza. Both diners share a pizza so S was subject to my gluten free choice – he didn’t mind, but I felt a bit sad because the gluten free pizza crust is thin crust, and we’d been keen to try a famous Chicago deep dish pizza if we could.


Sadly it wasn’t to be, but we tucked in to our thin crust pizza with gusto anyway. I was delighted when the couple two tables down from us got engaged – S won the wager on which couple it would be.

After finishing our meals, we were allowed to stay up on the Skydeck for as long as we wanted. However, I felt bad that the staff had to wait for us and it was nearly 1am, so after one last quick lap and a final 1,353 ft shoefie, we called it a night.


Back down we went through the sneaky back way in reverse, past the serious guards at the entrance, and home to our hotel. The whole way, we were shaking our heads.

What beautiful views.

What a city.


> Gluten free options are available! If limited. You can have the salad as an appetiser, there is a gluten free pizza option, but sadly there is no pudding that’s gluten free. You select your options, including the gluten free base, at the time of booking, and you can pick exactly what toppings you’d like on your pizza as well. I recommend the meatballs.


> Overall I’d say the food was ok, but not great. Pictured above is our salad…. Don’t do this for the food; do it for the experience.

> There are four glass ledges and there can be up to 9 tables per evening, but the other 4 couples in our booking were great at letting everyone have a turn in a ledge, taking photos of each other, etc.

> The drinks are free refill and you can have something different to what you originally ordered

> There weren’t too many cabs around at 12.30am so we waited a while to hail one. I’d recommend arranging one in advance if you can.

> Overall, I’d highly recommend this experience. It is $100 each (!) but seeing the city spread beneath us and being able to enjoy it at our own pace, with food, was a pretty special experience for us.


Have you ever dined at height? What did you think?


Linking up with Van, Marcella, Lauren and Isabel  for Wanderlust Wednesday and with Wander Mum and Mummy Travels for City Tripping

Thank you to my lovely family for contributing towards our dinner, we had an absolutely marvellous time and it’s an experience we’ll genuinely treasure.



  1. 5th October 2016 / 08:14

    Loved this post Rachel. Those views are breathtaking, although it would be a serious mental struggle for me to stand on that glass floor and look down haha. My husband and I are huge food enthusiasts and after moving to Tokyo made a resolution that we’d be splurging on fancy dinners versus buying each other gifts for each occasion. I think creating memorable experiences is so much more important and truly last a lifetime. 🙂

    • 6th October 2016 / 17:49

      It did take a minute at first but once you step on it and it doesn’t collapse beneath you, it gets easier! I think splurging on dinners instead of gifts is a great idea. I’m a big fan of food as well, and great memories plus a full belly is something that’s pretty hard to compete with! Plus you can generally take some great pictures of your experience, and looking at those will bring it all back 🙂

  2. 5th October 2016 / 09:46

    That’s a beautiful birthday dinner celebration! With my fear of heights, I wouldn’t have been able to enjoy the views, especially going anywhere near that ledge 🙂

    • 6th October 2016 / 17:50

      It’s definitely not an experience I’d recommend to anyone with even the slightest hesitation about heights! I don’t mind heights at all and even then it took me a minute to walk onto the ledge. Our cruise boat docent earlier in the day was saying how her grandson had jumped up and down on the glass – now that I couldn’t have handled!

  3. 5th October 2016 / 10:48

    Happy belated birthday! I’ve thought of doing that before – I’ve been up Willis Tower at night and it’s gorgeous. The only thing that could make the view better is GF pizza 🙂

    • 6th October 2016 / 17:51

      Thank you! It’s a great experience, I’d recommend it for a special event. And the gf pizza definitely made the whole experience for me! It even had gf meatballs on it. You really can’t go wrong with that.

  4. 5th October 2016 / 11:12

    This sounds like an amazing experience, although I do wonder why the 11 pm start time – it seems awfully late for Americans. As to the quality of the food, decades of experience have taught us that the better the view, the worse the food. It is an almost unbreakable rule.

    • 6th October 2016 / 17:53

      I think it’s because they let you in to the public viewing area after everyone’s gone home (and they’ve had a chance to clean?) and closing time must be later in summer due to longer days. It was awfully late for all concerned, I think it’s late even by Spanish standards and they eat later than any other nationality I know!

      I totally agree with you about quality of view vs quality of food. I was trying to think of an exception to the rule but… nope, can’t think of one. Also quality of view vs cost is the other side of the coin. If there’s a restaurant with good value, good food with a good view I’ve yet to find it.

  5. Jen
    5th October 2016 / 14:31

    Wow what an absolutely amazing birthday dinner this was! The view alone is worth it.

    • 6th October 2016 / 17:55

      It’s definitely a special memory. It was a great way to combine a few special occasions all into one and really go for it! I’m very lucky our family treated us 🙂

  6. 5th October 2016 / 14:31

    seriously what magical experience. i didn’t realize you could do a fancy dinner like that (so official). i can not stand out on that sky deck. i get so much vertigo with heights as it is so i’d be a mess ha. no one needs that. you look stunning too!

    xoxo cheshire kat

    • 6th October 2016 / 17:56

      It was all v official. Especially with the x-rayed cupcake. It’s ok if you aren’t keen on the ledge, there’s a whole pizza to be eaten so I think you’d have had plenty to keep you occupied whilst everyone else is scaring themselves on the ledge!

  7. 5th October 2016 / 15:27

    That looks like an awesome way to celebrate your 30th birthday! The view is gorgeous!

    • 6th October 2016 / 17:57

      It was! We’ll definitely remember that one. The view was magical, all twinkly lights and colours. We could also look down on all the late night goings-on which was quite interesting!

  8. 5th October 2016 / 16:34

    I about had an anxiety attack just LOOKING at you standing on that clear floor.
    I want to do that for christmas this year – more experience things than gifts that get tossed aside.

    • 6th October 2016 / 17:58

      Haha! Sorry about that! I’m not bothered by heights so I forget that others are!
      I’m all about the experiences. Let me know if you give it a go for Christmas and how it goes. Most people love it but some recipients are a bit confused by the whole thing!

  9. 5th October 2016 / 18:09

    I can’t believe that you actually looked down! I’m not scared of heights, but I was trembling so much and couldn’t make myself look at the pavement below. I think that it was the idea of a piece of glass holding me up so high in the air, and the fact that Chris kept on acting like he was going to jump when we were out there together. This sounds like such a fun experience, especially for a birthday celebration, and you can’t beat those views!

    • 6th October 2016 / 17:59

      I did! I mean I built up to it a bit, looked down with my feet on the building and then worked up to looking down with my feet on glass. But once I realised how sturdy it felt it was much easier. Plus it was cool to see all the way down! If S had tried to jump I’d have noped all the way out of there, but luckily he was more scared than me so there was no chance of that happening 🙂

  10. 5th October 2016 / 21:24

    i definitely could not step out on the side of the building like that, especially because it’s glass and just HECK NO thinking about it stop stop no.

    i want experiences for birthdays and christmas from now on. especially if they involve food!

    • 6th October 2016 / 18:01

      Yes! The ones involving food are definitely the best ones. I just think it’s the way forwards, for so many reasons. The glass ledge really wasn’t as scary as it might sound. It’s very sturdy and all kinds of reinforced, but I can see I’m not going to convince you on this one!

  11. 5th October 2016 / 22:38

    What an amazing experience, this looks great!! 🙂 I just can’t even imagine a view from that high up, it’s crazy to think of. And I so agree with you, experiences are so much better than material presents as those memories last forever – cheesy but true 😉

    • 6th October 2016 / 18:02

      It was a lot of fun, and a really different experience. I liked the feeling of going ‘behind the scenes’ and eating in a tourist attraction was oddly fun! The view was immense. I’m pretty sure I’ve never been that high before. You could see so far! And sometimes the cheesy sayings are the most true 🙂

  12. 6th October 2016 / 02:03

    That sounds like a great way to celebrate your birthdays! One day we’ll make it up to the Skydeck but I have not yet worked up the courage to face my fear of heights. Maybe someday. #wanderfulwednesday

    • 6th October 2016 / 18:03

      It was a fantastic experience and a great celebration. I personally thought it was a fun way to see the city, but if you’ve got a fear of heights I can see problems with that! If it’s any consolation the box really was very sturdy… And the view was crazy good!

  13. 6th October 2016 / 02:09

    How cool!! I’ve been up to the Willis Tower SkyDeck a few times, and out on the glass ledges, but not for an experience like this! That’s definitely a dinner to remember!
    I like both experiences and material gifts for birthdays–I think there’s a place for both. Our trip to Japan in July was our birthday present for each other…but I also got a curling iron from my mom which I love because a girl needs a curling iron, ya know? Cool travel experiences do not provide the gorgeous curly hair look. haha!

    • 6th October 2016 / 18:06

      The ledges are pretty cool, aren’t they? I’d have loved to see that view in the daytime, too. It certainly was a dinner to remember, and if I ever go senile then I’ve got the photos to remind me just how great it was 🙂

      There’s definitely a place for material gifts (and curly hair!) and usually I’m up for any type of gift anyone wants to give me, however we’re thinking of moving quite soon so extra things to move is not what we’re after right now! I expect that will change post-move…

  14. 6th October 2016 / 11:43

    What a cool experience! I’ve always wanted to go to the ledge in Chicago, but this looks like the way to do it! I’m so into gifting experiences rather than things these days! I’m by no means a minimalist, but I’m trying to get better about all the clutter. I’d so much rather have amazing memories than a bunch of junk! And with the security… Welcome to the US haha .. You have to go through high profile security almost everywhere these days…. :X

    • 6th October 2016 / 18:07

      Yeah no I’m definitely not a minimalist either, but after looking at what I’ve got to declutter that lifestyle is suddenly looking very appealing! The security in the US was pretty tight, it’s true, but everyone was so nice about it that I really didn’t mind. I’d rather be safe. We just learned to allow extra time, ha!

  15. 6th October 2016 / 12:49

    I think I will definitely sacrifice the food for the view in this case. The view at night looks stunning and super romantic, you looked very cute too!

    • 6th October 2016 / 18:09

      Oh the view made the slightly sad salad worth it 100%. And the pizza was good, so with good pizza what can you really complain about?! It was very romantic, I was so happy when one of the other couples got engaged! Now that’s a story for the grandkids. And thanks, you’re too kind!

  16. 6th October 2016 / 15:50

    What an incredible view!!! And you look gorgeous! Does the tower turn around too? There’s a tower restaurant in Trondheim here in Norway which turns around. I’ve been there on my very first trip to Norway and it was really special!

    • 6th October 2016 / 18:10

      The view really was breathtaking! No the restaurant didn’t spin sadly, but to be honest I think spinning PLUS ledge would have been a little bit much for me! I’ve always wanted to go to a rotating restaurant, though. Trondheim sounds like a great place for it, I can imagine the views would have been spectacular!

  17. 6th October 2016 / 18:18

    what a cool experience! I’ve been to Chicago loads and loads of times (grew up about 4 hours from there) but I’ve never done anything like this. I completely agree with you about putting a higher value on experiences over presents. it’s always worth it and always special 🙂

    • 11th October 2016 / 10:31

      Ahh lucky you, it seems like a cool place to be able to visit (albeit in 4 hours!). I think it’s easy to miss out on the big attractions in familiar places – I don’t know why, maybe we think we can go any time so don’t need to bother this time? I’ve done hardly any of the big sights in London, I’ve never been inside Buckingham Palace and I only went to the V&A this year. I grew up literally down the road from Windsor Castle and went for the first time when I was like… 15. Because I had an exchange student visiting! Ha.

      I’m all about the experience presents now. Family be warned!

  18. 7th October 2016 / 05:26

    Wow that is so cool! A once in a lifetime experience – especially how not crowded it is, seems very exclusive (despite the sucky food sadly). Seems like a nearly perfect way to mark a celebration 🙂 Happy belated birthday by the way!!x

    • 11th October 2016 / 10:51

      Definitely once in a lifetime. It was a great experience to mark an arbitrarily great occasion, so I couldn’t have been happier! The pizza was tasty so that’s all that matters. Who cares about salad anyway?! 😉

  19. 10th October 2016 / 06:45

    Wow, this is an incredible dining experience!! I totally agree with you… I’m all about getting experiences rather than things. I’d take over over diamond earrings any day! The views are stunning and I can imagine how scary it must be to step on that glass ledge… I’ve never been somewhere so high. Happy belated 30th! I’m glad you celebrated the end of a decade in such a memorable and glamorous fashion!

    • 11th October 2016 / 11:08

      Me too! I’d only lose them anyway, knowing me. The views were so pretty with the twinkly lights, such a cool way to see a new city. I actually really enjoyed being up so high and I’m now looking for other high up experiences to do! Thanks for the birthday wishes, it’s been quite a year. I figured it needed marking as such 🙂

  20. 11th October 2016 / 10:06

    Wow the place & the view are amazing!! I’d like to try to step on the glass floor, even though it looks kind of scary ;))
    They should have better food though to match the beautiful location!
    Happy birthday btw!! :))

    • 11th October 2016 / 11:12

      It was a pretty cool experience, I’m really glad I got to do it. I think on some evenings you can also see fireworks from up there, which is even more exciting! Great food would have been the ultimate, but I can understand that we basically got takeout delivered 103 floors up. We were too busy scaring ourselves on the glass ledge to care overmuch…! And thanks for the birthday wishes! I’ve had a blast this entire year so far so I’m definitely stretching out the celebrations…!

  21. 11th October 2016 / 10:08

    Wow.. That view was totally worth the strict security check and hefty price tag! I would be so tickled by seeing the cupcake getting an X-ray scan. I heard in Chicago, you have to eat deep pan pizza. Such a pity it didn’t gel with gluten free options there. #CityTripping

  22. 11th October 2016 / 17:26

    We totally agree on the experiences vs stuff thing, and I am so thrilled this is what you guys chose to do for your 30th!!! I don’t think I could bring myself over to the ledge, but I am proud of you for being tough enough to make it happen! Beautiful photos, Rachel, and what an incredible memory for you guys!

  23. 13th October 2016 / 20:00

    Oh wow, what an experience – and I completely agree, I’d much prefer to be making memories than accumulating more stuff (well with a few exceptions but those are usually cameras!) The views are incredible. I think I’d have been wary walking out on to the ledge as well at first. I’ve had dinner high up the CN tower which was wonderful, but it was sitting at a table rather than wandering around (though you got entry to the viewing area as well) so a little bit different. Thanks for linking up with #citytripping and happy (belated) birthday!

  24. 16th October 2016 / 08:36

    Fantastic night views! I went up the tower during the day and it’s quite a different experience. Well done for staying up so late. I’m definitely all about experiences – great way to celebrate your 30! #citytripping

  25. 16th October 2016 / 17:55

    This is truly a spectacular experience! Beautiful shots too!!! Absolutely great way to celebrate birthday. Happy belated birthday to you and S, btw. #citytripping

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