Harry Potter, WNDR, and Hot Dogs — Courtlin’s 2026 Trip to Chicago [GALLERY]

For only the second time in my life, I took a trip to the Windy City with a couple of friends this weekend! He's a rundown of all the things we squeezed into our 2-day visit.

Aragon Ballroom

The main reason for our weekend in Chicago was to attend a concert at the Aragon Ballroom. We went to see an emo band that I absolutely adored during my teen years called Boys Like Girls. Not only did we get to see them, but they played their entire first album front to back, which brought out the emotional 15-year-old girl inside of me. I was grinning from ear to ear the entire show, screaming the lyrics and thinking about all those walks home from school that the album got me through. If you ever get the chance to go to a concert for a band/artist you loved when you were younger but never got to see live - DO IT.

In addition to the awesome concert, the venue itself was absolutely one of the coolest places I've ever seen a show. The 100-year-old ballroom is designed to look like the courtyard of a Spanish palace, complete with a starry night sky painted on the ceiling. It's definitely one-of-a-kind!

After the show, we went to a place called Trader Todd's for karaoke and to watch the end of the Sweet 16 games. Other than the disappointment of seeing two of my chosen teams absolutely wreck my bracket, it was a wonderful night!

Lakeview Breakfast & Shopping

Our Airbnb in Chicago was located in the Lakeview Neighborhood, so that's where we spent the first half of our Saturday. We walked to breakfast at a longtime local diner called Golden Apple Grill & Breakfast House, which had good food and was perfectly located for people (and dog) watching. Then we headed back the opposite direction for shopping at the stores on N Southport Ave. We hit up Free People, Abercrombie & Fitch, Sephora, Anthropolgie, and a cute place with lots of Chicago gear called Alice & Wonder. Did I spend way more money than I had anticipated? Yes. Do I regret it? Only when I look at my bank account.

Harry Potter Store & Hot Dogs

One of the "must-do" things on my list for Chicago was a visit to the Harry Potter Shop on Michigan Avenue. After a quick break at our Airbnb, we took an Uber down to the Magnificent Mile to wait in line to get in. It only took about 5 minutes for us to get in the door, and then it was off to the races!

Before we left, I said to my friends, "I can't foresee myself spending a whole lot of money in there, I already have so much Harry Potter stuff already." 

*Pause for laughter* 

Obviously, I was wrong. I had a burst of strong nostalgia and ended up buying all sorts of goodies - a sweatshirt, a Christmas ornament, a magnet, a Chocolate Frog, a stuffed Bowtruckle, Butterbeer... even Butterbeer Ice Cream! The shop had all sorts of fun decor to check out, too. I think we spent about an hour in there wandering around.

After a couple of stops at other shops in the area, we stopped to grab dinner at a teeny tiny Devil Dawgs location, because we obviously couldn't go to Chicago without getting a Chicago dog. We had to eat our food on the street because there was absolutely no room inside, but it was so good that it didn't matter. 100% recommend.

Navy Pier

Our final stop on Saturday evening was Navy Pier, because there was a women-owned small business market happening that we wanted to check out. I had never been to Navy Pier before, but it was worth the stop for the view alone! And, before you ask, NO... I did NOT ride the ferris wheel (I hate ferris wheels!). I did, however, get a super fun Chicago dog shirt from a business called Local Style that I'm completely obsessed with!

We didn't stay at Navy Pier very long, because it was a bit cold and windy, but I'd love to go back in the summer and see it in all its glory. Next time!

Because we are old and exhausted, we never made it back out to any of the bars we wanted to check out on Saturday night. A good friend of mine that used to live in Chicago even sent me a list of great suggestions, but I will also be saving that list for my next visit.

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Brunch & WNDR Museum

We made plans to hit up a couple more places on Sunday morning before we headed back to Iowa, because we wanted to squeeze as much as possible into our short weekend getaway. We knew we wanted to hit up one of the Instagram-worthy museums in the area, so we settled on the WNDR Museum in the West Loop. We bought our tickets ahead of time to save money, and then looked for a nearby brunch spot that we could head to first. That's how we ended up at Chicago Waffles.

I didn't end up getting waffles, but my friend ordered the Waffle Flight and let me try them. The Nutella & banana one was easily our favorite! My brunch choice was the breakfast burrito and a side of potatoes, which was absolutely delicious. Plus, the decor inside the restaurant was really fun. There was even an American Gothic painting with dogs instead of people!

The WNDR Museum was about a 3 minute walk from the restaurant, so we made it in time for our reserved ticket time (you save money that way!). It features 15 immersive art installations, including a room where you get to see a photo of your iris up close, a 3D area, and a taste-test with a special kind of berry that alters your taste buds. Overall, it was pretty cool! Next time we want to do either the Museum of Ice Cream or the Balloon Museum (open until September 7th).

Check out all of my photos from my 2026 trip to Chicago below:

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