MY FIRST TIME IN CHICAGO! CHICAGO SPRING 2025 TRAVEL GUIDE

This is a fun year of checking off new cities on my bucket list! I just got back from my first trip to Chicago, and I fell in love with the city. This trip was especially fun since it was a family trip—my mom and I flew there and stayed at my uncle’s house so we could celebrate my aunt’s graduation from Loyola. We really enjoyed getting a local’s perspective, so here’s my Chicago spring 2025 travel guide with where we ate, what we did and what to wear.

WHAT TO DO IN CHICAGO SPRING 2025

Since we were there to celebrate my aunt’s graduation from Loyola, we didn’t “do” a lot of typical tourist things! I’ll share a list of what we did + what’s on my list for next time.

Walk along the beach

My uncle lives in Rogers Park which is right next to the lake, so we took a few walks along the beach. I was in awe of seeing the beach and the water (that looked more like an ocean) with a backdrop of a huge city! I’m so used to going to Gulf Shores and Orange Beach which are much more lowkey, so this was really fun to see.

Check out Loyola’s campus + the Madonna della Strada chapel

Loyola’s Chicago campus is absolutely beautiful, and despite the cold, it was so fun to explore and walk around! On Sunday morning we went to Mass at the Madonna della Strada chapel which was one of the most beautiful chapels I’ve ever been to. If you’re Catholic and visiting Chicago, highly recommend adding that to your list.

Top recommendation: visit the Art Institute

WHERE WE ATE

Giordano’s

Obviously I had to try Chicago-style deep dish pizza! My uncle recommended this spot in Rogers Park so we ate there on our first night, and it was delicious. I did a build your own pizza with chicken sausage, peppers and olives, and the individual pizza was big enough that I had leftovers the next day. Deep dish pizza isn’t my favorite, but Giordano’s also has a ton of other options if you’re not a fan.

Ann Sather

This is another Chicago restaurant with a few locations, and we went after Mass on Sunday morning for brunch! They serve Swedish food and have tons of breakfast options, and they’re known for their cinnamon rolls. I wanted to have a true taste of everything so I got the Swedish breakfast sampler. It wasn’t my favorite meal ever but it was a ton of food so definitely worth it if you have a hungry group.

Devil Dawgs

Another must on my Chicago spring 2025 bucket list: a Chicago-style hot dog. I don’t really get what Chicagoans have against ketchup on their hot dogs, but I respected the tradition and got a hot dog loaded up with pickles, peppers, mustard, onions and tomato. Just like the deep dish pizza, I’m glad I tried it but it definitely wouldn’t be my go-to. Devil Dawgs was fantastic though and had fries that were 10/10.

Honeybear Cafe

On Tuesday morning, we went to the Honeybear Cafe for a big brunch. I got the chilaquiles which were so delicious (one of my favorite brunch orders on trips because it always reheats well!). They were super crowded on Tuesday around noon, but the hostess was so nice and we were seated relatively quickly. Plus, they give you tiny cheesecake bites with your meal which is so fun!

Calo Ristorante

After my aunt’s graduation, we went to Calo Ristorante for a celebration dinner. This spot was fabulous, and I’d definitely go back. I got the caprese rigatoni and one of my regrets of the trip is I didn’t finish the leftovers the next day! My mom and I also split the limoncello mascarpone cake which was phenomenal. Such a vibey spot.

Fairgrounds Coffee

Obviously my Chicago spring 2025 travel guide is going to include coffee! My favorite coffee stop of the trip was a local chain called Fairgrounds in River North. They serve coffee from a few different roasters, and the salted caramel cold brew I got was the perfect balance of sweet and creamy. .

WHAT TO PACK FOR CHICAGO SPRING 2025

Like I mentioned, this was my first time in Chicago and while I knew the city was known for being cold and windy, I really didn’t pack well for the first half of the trip! It was warming up as we neared the end of the trip, but because of the water, there’s definitely a chill in the air, so pack lots of layers. We were there in early May and I would have done well to pack more jackets.

Here are my recommendations for a few things I packed that I wore over and over again and what I wish I had packed:

Comfortable (but cute) shoes: I almost always bring multiple pairs of shoes on trips and then exclusively wear one pair, so if I have a pair that’s comfortable and looks just as good with dresses as it does with athleisure, I know I’ve found a winner. My current favorites are Sam & Libby sneakers—my go-to pair right now is neutral with a pop of green and works nicely with so many outfits. These are comfortable enough for full days walking around which is such a necessity!
A jacket (or two) that matches everything: Mom came to the rescue for this trip because I borrowed one of her jackets most days. Chicago in spring seems like a mixed bag of weather, so if I visit again in the spring, I’d bring at least one jacket that could work with every outfit.

Chicago was definitely a bucket list U.S. destination for me, and I cannot wait to go back soon!