Chicago Guide City | One Small Blonde

Welcome to the Windy City Guide! Finally getting around to sharing all about the city I’d move to if I ever had to leave Dallas. Yes, if there was one other city I’ve considered moving to it’s definitely Chicago! I just can’t seem to wrap my head around those winters…

Surprisingly, I’ve been to Chicago three times before this trip and they were all during the winter months. Crazy, right? How had I not been up there during the prettiest time of the year? And it was exactly that…gorgeous. Literally, we had the absolute best weather and trip. Just writing this post is making me want to plan another trip ASAP!!!!

The reason I went up to Chicago in June was actually for a friends wedding in Milwaukee, but if I’m going all the way up North then I knew I had to spend a few days in Chi Town. First things first, if you need a place to stay then you should 100% consider The Conrad Chicago. It’s got the best location (literally walked everywhere) and two amazing restaurants. Drinks on the rooftop at Noyane was so much fun!


Chicago City Guide | One Small Blonde


Conrad Chicago
The Langham
Thompson Chicago
Kimpton Hotel Monaco



Refined Cotton Ruffle Shell

Through the Vine Maxi Dress FREE PEOPLE

Chicago City Guide | One Small Blonde

Shockingly, I’d never been to Willis Tower or done a River Boat Architecture Tour during any of my visits. Obviously I went to Cloud Gate or “The Bean” on my very first trip because it’s the thing to do. (*I recommend going really early before the crowds! Get your coffee, walk to The Bean and then brunch!) I’m not going to lie…I thought I’d b fine at The Skydeck at Willis Tower because I’ve done the Eiffel Tower in Paris so the height didn’t bother me. WRONG. It’s a lot higher. Basically, I crawled out into the box to get the picture above, haha. The things I do for a good blog photo!

I think riding the Divvy Bikes along the shore and taking the Riverboat Architecture Tour were my favorite things to do. The Divvy Bikes are great because you can pick them up anywhere in the city. Also, we rode around for a bit before finding a spot for lunch. That night we decided to do the Riverboat Architecture Tour, but just FYI there are a few different ones! In addition, we did the one where they had themed nights so we got to do a “BBQ & Beer” boat ride which was SO much fun. I forgot the name of the company but ask around!!!


Millenium Park
Cloud Gate (The Bean)
Willis Towner
Cubs Stadium
Divvy Bikes
Architecture Tour
Michigan Ave.

Gathered Sweater Tank MADEWELL

Fringe Hem Sweater Shell

brunch in chicago

Okay so let’s talk about the most important part of any city guide…the food & drinks. Duh. Chicago has sooo many amazing spots to choose from it’ll be hard to hit them all, but we did pretty good. I’d say my absolute favorite spot is Cindy’s Rooftop. The views are incredible! (*Make a reservation!!)

However, I can’t tell you how many people told me to go to the cafe at Restoration Hardware. I thought they were joking, but oh no… It’s ah-mazing!! Totally a perfect spot if you are doing a girls weekend. I don’t think I talked to my friend much because I was so in love with the decor and people watching.

Now let’s talk pizza…deep dish obvi. I’ve only been to Giordano’s Pizza which is probably the most popular. After a 45-minute wait for pizza I was getting a little hangry, but definitely worth the wait. I prefer my pizza thin crust, but I promise just try the deep dish.


3 Arts Club Cafe (Restoration Hardware)
Giordano’s Pizza
Hampton Social (*Rosé All Day wall)
Baptise & Bottle
Summer House
Radio Anago
Tied House

where to eat in chicago

Chicago City Guide | One Small Blonde

Now if you just want a good spot to grab a drink I’ve got a few recommendations. I mentioned Noyane earlier because it was in our hotel, but even if we hadn’t have stayed at the Conrad Chicago I would still tell you to go get a drink there. In addition, the rooftop is beautiful and right in the city.

We kept trying to go to The J Parker because a ton of people told me to go there, but we just didn’t have time. It’s on my list for next time! Also, I follow this cute Chicago blogger, and she had just posted about Z Bar so that was on my list too. However, it had just opened so getting in was a bit difficult.


The J Parker
Z Bar
Cindy’s Rooftop
Ballast Point Brewery

Chicago City Guide | One Small Blonde

Even though this isn’t really part of Chicago, I totally recommend renting a car and taking a drive up the Michigan Lake shore. We found this adorable spot with this beautiful lighthouse and it was a huge highlight from the trip!!

What do you all love about Chicago?! I’d love to hear your recommendations for next time!

2 Responses

Leave a Reply

Your email address will not be published. Required fields are marked *