24-Hour Chicago City Guide

Hey everyone! If you follow the NOT UR AVG Instagram, then you know that I was recently in Chicago, Illinois. I actually had to go there for a work conference, but I made a little trip out of it by going one day early and staying one day later! I was pleasantly surprised with Chicago; it reminded me of New York City, except way cleaner. I would definitely go back to explore more of the city and nightlife, which I didn’t have a chance to see.

If you don’t have much time in Chicago, these places are a MUST. Enjoy!


Obviously I would start off with this. What better way to explore a city and its culture than through food?

Lou Malnati’s

I always ask the locals what they consider a must-see when traveling and I kept hearing about this place over and over again; the guy on the plane, our uber driver, the front desk at the hotel… This pizzeria is apparently home to the best deep dish in Chicago. If you didn’t know, Chicago is known for it’s deep dish pizza – basically a fat pie, but instead of apples it’s sauce, cheese, and vegetables. A LEGIT PIZZA PIE. It was incredible!!


For those of you who are familiar with the TAO Group, you know that they have restaurants in many cities worldwide. I’ve spoken about TAO on the blog before, because I’m a huge fan of the one in NYC. TAO Chicago pretty much has the 75% of the same menu, but when something is good, it’s GOOD. I’ve been for many different occasions. Make this your go-to spot for a romantic dinner, bachelorette party, company gathering – I’ve done it all and it’s always a good time!

When ordering, I highly recommend the Miso Roasted Black Cod, Spicy Eggplant side, and Warm Chocolate.

The Black Cod & Eggplant side!!


Millennium Park

This infamous, public park is located in the Chicago Loop (basically the center of town) and is home to all of the famous Chicago monuments you’re probably already aware of. It’s such a nice daytime activity because of the park’s cleanliness, proximity to the city center, and activities. From free beer, a boxing match, to rock climbing, Millennium Park is a great way to spend your day!

The Cloud Gate aka “The Bean”


Crown Fountain

Navy Pier

This beautiful area is the calmest part of the city. This is the place where you truly experience why Chicago is coined the “The Windy City”. The large gusts of wind by Lake Michigan definitely call for an up-do… and GREAT photo ops.

SkyDeck at the Willis Tower

This is a MUST when visiting the Windy City. The SkyDeck is a bit scary because you are standing on a glass floor 1,400 feet above the ground on the 103rd floor… but WOW what a view! It held the title of the tallest building in the WORLD for 25 years.  Now, it’s the 2nd tallest building in the U.S. after the One World Trade Center.

Disclaimer: Once you get to the top the Willis Tower, you have to wait about half an hour to take a photo in one of the observation decks, but it’s 100% worth it.

Chicago is a beautiful city with truly incredible architecture. I stayed at the W Hotel in the City Center. It’s located in an amazing part of town and has a really beautiful lobby. The W has an amazing breakfast (extra charge), but the rooms themselves were super small. All in all, I really wish I had some more time to explore, but Chicago, I’ll be back!






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