Over Sarah’s 2026 Spring Break we decided to check out Chicago. We’ve never been and have heard great things but also we can get a direct flight from PSP to ORD which, let’s be honest, is a top-tier consideration these days. I wrote about the great food we had in another post, if that’s what you’re here for, otherwise continue on for some of the neat places we visited and things we did.
Architecture Boat Tour
As you probably know, Chicago is a city built around a river which makes it a very unique and interesting place to visit. It’s also in many ways the birthplace of the modern skyscraper and the locals are quite proud of both. As a result, there are several boat tours you can take through the city which not only get you a unique vantage point from which to view the buildings but you’ll also learn a bunch about them along the way.
Once upon a time I planned on being an architect, so the idea of boats + architecture facts was already of interest to me. Sarah was unsure whether she would get anything out of the tour guide’s ramblings and as it turned out – she did! Here are some shots from that tour, which I’ll warn you can get pretty brisk (we were there in April) – so bring layers.
As I’ve often said on this site, these photos really don’t do these buildings justice. It’s worth going to see for yourself. The tour group, which was led by local architects who volunteer their time to tell you all about the buildings and their history, is Chicago Architecture Center River Cruise. We were quite pleased with them.
360 Chicago
One of the tallest buildings in Chicago has an observation deck that gives you a… wait for it… 360 degree view of the city. You have to pay to go up, but it’s not crazy expensive (book online, it’s cheaper – we did that from our phones in front of their ticket desk) and for an extra fee you can pay to be dangled over the edge of the building. I’m kidding, but not really… it’s called The Tilt – though we saw an old woman in a walker doing it so I’m not quite as metal as you’re imagining.
There’s a bar at the top for those of you who want to take in this view on hard mode. It’s worth a visit, if you ask me. I mean, you didn’t ask, but if you did… 360 Chicago.
Wrigley Field… Finally!
Visiting Wrigley is a bucket-list item for me. I love baseball stadiums and this is about as classic as they come. Due to the time of year, the iconic ivy wasn’t out in full force but it was still a near-religious experience (whatever people mean when they say that).
As we were trying to get a selfie in front of the Wrigley sign, a dude in a Phillies hat offered to take our photo. Turns out he’s from Souderton, PA… small world (not far from where I grew up, for those of you reading from outside Pennsylvania).
We just sorta lucked out that the Phillies happened to be in town while we were there. I’d have gone just for the stadium but it was extra special to see so many other Philly supporters there (Philly fans TRAVEL – any time I’ve seen them at an away game it’s almost hard to tell who the home team is). This was like game 10 of a nearly 10 game losing streak for the Phils, but they put up a great fight… losing in extra innings.
Art Institute of Chicago
You could easily spend the entire day here. The building itself, like many museums, is a sight to see. This museum is also home to many very famous works of art. I tried not to be on my phone too much because I wanted to just take it in, but I did grab a few pictures of pieces I thought were particularly interesting (and one that you might recognize from a famous scene in Ferris Bueller’s Day Off 😉)
I’d tag the Art Institute of Chicago as a must see.
Fun side note, my Aunt Susan is a professional artist and I was sending her some pictures while we were there. The last photo, of the creepy person statue, was one I thought she’s really appreciate – she immediately shot back with the artist’s name (Giacometti) and confirmation that they’re indeed one of her favorite artists. Feels good when something makes you think of someone else and it lands 🙂
Bean Park (I know the real name and I don’t care)
This park is directly across from the Art Institute and had all sorts of neat walkways, art installations, gardens (if you’re not us and instead go when they’re open), an outdoor climbing gym, a locally-themed mini golf course, playgrounds, and some sort of roller skating loop. It’s a really neat park. It of course, is also home to the The Bean, which honestly is one of the coolest sculptures I’ve ever seen in person. Whatever you think it’s going to be like, your brain is underselling it.
A lot of the stuff I mentioned above is missing from my Millenium Park entry because they were closed for renovations.
Chicago at Night
Whatever you might think of the skyline during the day, Chicago is especially stunning at night. We walked along the river after our dinner at The Girl and the Goat because it was such a beautiful night – also because we ate far too much and were dreading laying down without burning some calories first (a sentiment that should be represented on Chicago’s official flag)
The Magnificent Mile
I suppose this is what they call Chicago’s “shopping district”. It’s a relatively short stretch of stores… presumably roughly a mile… just north of the river that cuts through the city. It’s where the Starbucks Reserve and Harry Potter stores are. It’s also not far from 360 Chicago.
We were there during some sort of flower festival, so the streets were all done up with tulips and other flower sculptures. I’m not really a shopper, but this was still worth the walk. It’s a neat area. I’m also going to include a photo we took at the Navy Pier which was… neat, but not really deserving of its own section.
