Chicago Guide | 2 Day Itinerary

September 26, 2022

Here's how to make the most of your time in Chicago!

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Here's how to make the most of your time in Chicago!

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Here's how to make the most of your time in Chicago!

Here's how to make the most of your time in Chicago!

You've got TWO days in the city. How do you make it count?!

I've been to Chicago a few times now, but this was the first trip where it wasn't *frigid* outside, and wow it was so enjoyable! Ha! 

Here are a few of my top picks to enjoy your weekend in Chicago.

the view from our room on the 33rd floor at the Pendry Chicago


Let's quickly cover hotels/neighborhoods to stay in! Honestly, it's no fun when you have to take an Uber *everywhere* in a walkable city because you chose to stay in the wrong area. I wrote an entire post reviewing our stay at The Pendry Chicago and it was the most amazing location and a great experience overall.

I recommend staying on the north side of the loop/downtown or in River North. You'll be close to restaurants, shopping, and the beautiful river! 


First things first, you obviously know you have to try deep dish pizza if this is your first time to Chicago. Tbh I like regular pizza better, but you have to go for it to get the full experience.


My favorite of the deep dish spots I've tried is Giordano's. Be prepared for a wait, but they've got the system down - you order before you sit down! It takes about 45 minutes to prepare the pizza, so you order ahead of time! Love it. There are multiple locations, but we walked 2 blocks from the hotel to visit this one!


Adorable cafe on the outside AND a swanky french brasserie and oyster bar on the inside. We *loved* Venteux and it was inside the Pendry! We actually ate brunch there and dinner one day! Both so good! The cafe out front is perfect for a quick bite or coffee, and the restaurant inside was beautiful and moody with amazing french food. Can't go wrong with either! 

Garrett Popcorn

I know, it's popcorn, but it's a staple. I'm not a huge popcorn fan normally, but when in Chicago, I love stopping by Garrett for a fun treat! Their popcorn is so good! It's only good for 24 hours, so you have to eat it right away ;) 

The Sites

The Bean

Of course you have to visit the Bean to get your selfies! It's literally a giant metallic bean-shaped sculpture inside Millennium Park in downtown Chicago! I love that you can see everyone hiding underneath the Bean while it was raining, but our hotel gave us an umbrella, so we were good to go with our tripod photos! Love them and that you can see the reflection of downtown Chicago in the Bean! It's definitely a tourist spot, but you're a go enjoy it!

Chicago River Cruise

Cruising the river was one of my favorite activities! We are members of a boat club in Dallas and they have reciprocal club locations in Chicago so we were able to reserve a boat while we were there and take it out on the river! It was so fun to cruise through downtown on the river! (lol at us waving at other boats go by).

We also went out onto the lake, BUT they have the *worst* system for getting out of the river onto the lake...I won't go into detail here, but if you do want to go out onto the lake, research the river lock system!! I loved the river, so I would recommend staying on the river.

You don't have to rent a boat to enjoy the river. Absolutely do a dinner or architecture river cruise!

The Riverwalk

The weather was glorious on Saturday while we were there, and the river walk was the perfect spot to relax outside and take it all in! Grab a beverage and people/boat watch during the afternoon! 

Ride a Bike

One of my favorite tourist activities in any city is to ride bikes! I don't even ride a bike when I'm at home, but there's something so fun about doing it on vacation! We rode from the Pendry to Navy Pier, which is Chicago's boardwalk area and it was so fun! Highly recommend biking around if your hotel has bikes available! 

What are your favorite spots in Chicago? See my trip on my Instagram highlights @rhondajenkins!

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