CHICAGO, ILLINOIS

Towards the end of October was when I traveled to The Windy City for the first time! It was a weekend trip packed with a lot of things to do and delicious places to eat. If you want to cut to the chase, scroll down to view my recommended Must Go To Places/Restaurants.

 
 

Itinerary by Sygic

https://maps.sygic.com/#/?trip=59977a242f0ce

The itinerary is designed to conquer the major attractions in Chicago. There’s much to see in this city and thankfully my friend Byron C. created this itinerary to take advantage of our time during this trip.

Plane Tickets

We flew with Spirit Airlines and paid 89$ for a 4-day roundtrip ticket. Once again, we searched for our flight using Google Flights and chose this date because of the low price.

Hotel

We stayed at The Gwen - Michigan Avenue Chicago, which is connected to a shopping center that has many brand name stores and is also surrounded with many different restaurants. The hotel itself has a roof top bar/sitting area and is nice to visit during sun down. They accommodate fire ranges during the chilly temperatures. The hotel has a modern style with a luxury sense to it. We never ate at the hotel, but they do offer breakfast!

Temperature

They don’t call it the windy city for no reason. We went late October and the temperature was around 55 -65°F. There was a day that the sun was out and we were holding our jackets instead of wearing them, so don’t worry about bringing many big jackets. (Need packing tips for cold weather? Click here.)

 
 

Chicago, Illinois

Enter Aly’s Photo Gallery

 
 

Must Go To Places

  • Cloud Gate / The Bean: A touristy place so expect A LOT of people around the iconic bean. If you are wanting a picture without anyone around, then you’re going to have to wake up early. The photo I uploaded at Cloud Gate is not photoshopped. We literally woke up early to come out there in the cold and take a picture. It’s pretty cool because there’s a handful of people doing the same thing and instead of someone photobombing your picture it’s basically an unwritten rule to form a line and wait till it’s your turn.

    (See the difference time does with the pictures below)

 
 
  • Apple Michigan Avenue: If you love design/architecture or are interested in simply checking it out then this is a must go to places for you. It’s a collaborated work with Apple’s Led Chief Design and Foster + Partners, and they created such a beautiful design implementing a thin carbon fiber roof that’s supported on slender stainless-steel columns. The detail and thought behind this project is one to check out! Read more about it here…

Must Go To Restaurants

  • Wildberry Pancakes & Café: The wait is looong but sure is worth it. What we ended up doing is leaving our name and phone number, which allowed us to go walk around and explore Millennium Park a bit more. Later on, we were notified that we were up next so we headed back to the restaurant. I ordered pancakes, eggs, hash browns, and a vanilla latte. It was all delicious and I definitely had leftovers. Join the Waitlist here…

 
 
  • Giordano’s: Chicago’s famous stuffed deep dish pizza. The wait wasn’t too shabby, and we got sat within a 30ish minute wait. Surprisingly, I didn’t order a stuff pizza and instead got a normal style pizza, yet it still tasted great!

  • Garrett’s Popcorn Shops: BEST POPCORN OUT THERE. They have a few shops around the city, and it’s seriously so good. You can mix and match in your bag. I definitely brought some back to Texas with me.

 

Have questions about traveling to Chicago?

*Disclaimer: This post is not an advertisement or collaboration with the following companies that have been listed. All expenses were paid with my own money.* (Read more about my reviews here.)

 

Chicago