The original purpose of our trip was to go to the Karol G concert. We booked it back in June 2021 right after buying the concert tickets, but the day of our departure I got on Instagram and viewed Karol G’s stories. That’s where I found out about the cancellation/postponement and was so bummed! 🙁
If you know me, you know I haaaaate a change of plans but not being able to go to the concert anymore wasn’t going to keep us from visiting Chicago that weekend. It was a place on our bucket list and we already had the flights and hotel booked, plus some additional activities, so why not have a mini weekend getaway? 😃
In this guide, you’ll find everything from cost, to where we stayed, what we ate, where we went, and what I wore. For the outfit details, you’ll find commissionable links that will take you to certain products. I may earn a small commission when you purchase through one of the links on this page at no additional cost to you.
The Cost
As with almost all of my blog posts from trips we’ve taken, I like to show a breakdown of the cost or what our total number ended up being. I do this mostly so you can see what a realistic budget would be and have an idea if you plan a similar trip in the future. I also like to look back on it for myself and reference it whenever we plan other trips and use the numbers as a guide on whether or not it’s something we’ve done before or if it was a good deal.
This is the cost breakdown of our trip:
- Hotel for 2 nights: $336
- Flights with Southwest (roundtrip for 2): $525
- Tickets to Skydeck (expedited entries): $110
- Digital photo at Skydeck: $31
- Magnet from Skydeck: $7
- Tickets to The Office Experience: $120
- Souvenirs from The Office Experience: $66
- Uber/Lyft rides including tips: $103
- Food including tips: $210
- Chicago souvenirs (tshirts): $31
- Economy parking at MCI: $22.50
Grand Total: $1,562
The Hotel
We stayed at the Hilton Garden Inn Chicago Downtown Riverwalk. The location was very convenient as it was only an 8-minute walk to the bean (south) and an 8-minute walk to The Office Experience (north) with so many places to visit in between. The drive from the airport to the hotel was about 30 minutes.
Our room was on the 3rd floor and it was the King Bed with City View room…although there wasn’t much of a view. 😆 I was kind of disappointed when I looked out the window just to see the front of the building across the street.
By the time we arrived at the hotel Friday night, there weren’t many food places open. We walked over to Broken English Taco Pub at 10:20 pm thinking there was enough time since they closed at 11 pm, but they had already locked the doors. So we went across the street to Billy Goat but they were also closed. We tried one more place before finally going back to the hotel and thankfully their restaurant was still open so we were able to get some chicken tenders, fries, and a flatbread.
Our room rate included 2 vouchers for continental breakfast during our stay. When we went down for it on Saturday morning all of the trays were empty and they mostly just had muffins and bread left. Any hot items were available at an extra cost and a little while later they brought out more fruit. We ended up having some fruit, yogurt, and a muffin for breakfast. The receipt said each breakfast would have been about $9 each (without the vouchers) which in my opinion wouldn’t really be worth it based on what we got.
Overall the hotel stay was pretty comfortable. All the staff was really nice and they held our luggage on Sunday for 6 hours since our flight didn’t leave until late afternoon and we wanted to go out and about beforehand.
The Food
We were SO looking forward to all the food in Chicago. So much so that when our plane landed at 9 pm we looked for a nearby place to grab something, but by the time we got to our hotel and checked in, it was already 10 pm. We tried a few places but they were closed so we ended up getting some chicken tenders, fries, and a flatbread from the hotel’s restaurant.
The fries were good and the flatbread was the best, but the chicken tenders were a little weird. They weren’t thick and juicy but instead thin and a little too processed.
The hotel breakfast the next morning was alright. I mentioned it above in more detail but it wasn’t anything special. We had plans to go to Fulton Market Kitchen afterward for an “adult donut” before heading to Skydeck, but when we got there we were told they weren’t making those anymore. 🙁 Below is a picture of what I saw on their Instagram that made me want to try it. It’s basically just a donut with a little bit of alcohol that you can inject into it.
Since we were already there, we ordered a breakfast sandwich and split it in half. It came with a side of breakfast potatoes, but they honestly didn’t taste good at all. Something about the seasoning they used, was too much of something that I can’t really put my finger on. Neither of us liked them no matter how much ketchup I drenched on them. And if you know me, I literally always finish anything in potato form so this should say something about that. 🤣
After Skydeck, we got a donut (yay!) and a Nutella iced latte (even though we’re not coffee drinkers) at one of the shops by the main entrance.
We still really wanted to try the taco pub so we decided to walk over at around 6:30 pm. But, attempt #2 to eat at Broken English Taco Pub was a fail once again. They only took reservations so we booked one for 8:30 that night, hoping that third time’s the charm!
Meanwhile, we had a snack at Five Guys right around the corner. And I don’t have to tell you how good their fries are.
Finally, we made it into the taco pub!! I got 2 tacos al pastor and 1 carnitas taco. David ordered 3 carne asada tacos and chips & salsa. The salsa wasn’t your typical “Mexican restaurant” style salsa. It was authentic and had a little bit different flavoring to it. The tacos were INCREDIBLE, although the carnitas one was too salty. My favorite taco overall is always the tacos al pastor and these did not disappoint.
We also got some drinks, but I thought they were all too strong. I liked the one David ordered more than the one I got (of course). I don’t remember the names exactly, but I think his was a margarita and mine was either a paloma or something else.
Our last meal in Chicago was the best one. Hands down.
After The Office Experience, we walked over to Lou Malnati’s Pizzeria. The wait was about 45 minutes because once again we didn’t make a reservation since I wasn’t sure what time we’d be done with our activity, but let me tell you, sooooo worth the wait!
When you first walk in, it looks like the top of a subway station with the staircase that goes down. I didn’t know how big the main area was until we went down for our table. The vibe upstairs was completely different than downstairs.
Our server was really nice and we ordered an appetizer with half boneless buffalo wings and half boneless parmesan wings. We also each got a personal size deep-dish pizza with whatever toppings we wanted (I got cheese, David got an Italian meat one). And for dessert, we ordered the Cannoli Dip.
It took about 40 minutes to get all our food. Partially because they couldn’t get the wing order right so that ended up coming out at the same time as everything else. But, they were nice enough to not charge us for those. At first, they brought out just a plate of bone-in parmesan wings. When David told him it should’ve been boneless plus half should’ve been buffalo the water took them back. He came back later with just a plate of boneless buffalo. 😂 He left those and came back a while after with another full plate of boneless parmesan wings after our other food had already come out. So we got double the wings at no charge which was really nice and so much more food than we could eat on the spot. We took the rest to-go and ate it before our flight that day.
The Activities
Skydeck
I first saw this on Pinterest and I thought it was something in New York until I looked at it again and saw it was in Chicago too! We booked through their website and got the expedited tickets. In my opinion, paying $20 extra for each ticket was worth not having to wait. Especially since our time was so limited on this trip. If we had been there for a week it would’ve been different but with only having 1 whole day to do whatever we wanted I didn’t want to spend any extra time that would add up to 1+ hours waiting in a line.
The mask requirements were very strict. We only took them off when we took our pictures on The Ledge. The time slots were also very strict in the sense that if your designated time was for 12:30, you couldn’t go up a minute before. Unfortunately, we didn’t walk through the “museum” portion of it. I’m not even really sure where it was because the path we took led straight to the elevators and I didn’t see any signs that would have led us another way.
Once in the elevator, there was a TV screen that gave you facts about different monuments and their heights compared to Skydeck. It was really interesting to read and as we reached the 103rd floor the shakier the elevator got. But it’s ok, that’s what it’s supposed to do. 🤪
To take our pictures on The Ledge, there was another line we had to stand in. There was also an expedited line and a regular line which was twice as long. Once it was our turn, we were told we had 60 seconds to take whatever pictures we wanted. The worker also took one of us and I’m not sure if this was included in the 60 seconds or not. Regardless, take this into account when you’re booking and evaluate if it’s worth it to you. Personally, I would say yes. But it’s a lot of money to only get a minute on The Ledge. It’s also understandable when there’s a large number of people to get through.
Although we only had a minute on the main part, we still were able to walk around the rest of the floor and take in the views. This floor was surrounded by windows so it was really easy to see the city from multiple points of view.
The Bean
The famous Cloud Gate aka The Bean. It was pretty cold and cloudy when we went so I was surprised to see so many people there and even a quinceñera LOL. It made it kind of hard to get a picture with the whole bean but we found another couple that was trying to get pictures too so we did a pic for a pic with them.
I really enjoyed finally seeing this famous art piece in person, but other than looking at it and admiring it there wasn’t much else around it. It looked like they were in the process of setting up a Christmas tree close to it and maybe even an ice skating ring but I’m not 100% sure.
The Office Experience
Other than the concert we were originally going to go to, this was what I was most excited about.
When we first walked in, security checked our bags and coats. Then, before we could go up the escalators to check-in, we browsed the gift shop since we were 15 minutes early and couldn’t go up before our time slot.
I felt like a kid in a candy store going in!! 😄
The overall experience was really fun, once we got through all the waiting. Honestly, I was getting really annoyed at one point not knowing why there were even any time slots to sign up for if we were still going to be waiting around for over an hour. (I know, first world problems) 😆
We signed up for the 12:30 slot but didn’t get to go into the main area until a little after 1:30. The main form of entertainment before making it into the actual office portion was a room full of facts about each character. Everyone was in a line so you couldn’t walk around this room, but there was plenty to read while we just stood there.
I think they did a really good job portraying every detail from the show. Everything from the reception desk to Michael’s office and the conference room. Even having Sprinkles in the freezer, ha!
It’s harder to put into words the whole experience, but if you want to see a walkthrough of it all in under 2 minutes, watch the video I posted on Youtube here. I posted it a few days after the trip on TikTok, but they muted it because of copyright issues so I deleted it and posted it again under a non-business account, but the same thing happened again. So far, Youtube hasn’t had a problem with it.
The Outfits
Here are some outfit details from the trip!
