The Ultimate Chicago Travel Guide

As a traveler, there are always tons of places that I want to go. And as a native city girl, I am always one that enjoys visiting other cities to see how they compare. So when the chance came up with Choose Chicago to head to the Windy City with my gals, the Babes That Wander, it was a trip that I was immediately on board to take. It brought together my love for the city and my love to travel with a group of likeminded diverse women to enjoy experiences together which is exactly where this Chicago travel guide is passioned from.

Chicago is a unique city to visit. It has great places to wander and fully experience. There are so many surprises such as finding a beach that seems like you stepped onto the beaches of Miami right in the city itself.

During this trip with the girls, I had such a great time and this Chicago travel guide has my heart and soul in it to give you all insight into great places to eat and stay as well as little tips to help you navigate the city and get the full experience of your travel when you visit.

There is so much that you’ll find in this Chicago travel guide, but if you’re looking for deeper itinerary or have just some general questions, make sure to leave a comment and I promise to provide you the answers that you need.

DINING IN CHICAGO

Chicago’s food scene is eclectic and very delicious. I wouldn’t say that I am a picky eater but I am quite particular on the foods that I eat and whether they are actually flavors that I’ll enjoy. During our trip, we were able to visit a variety of different restaurants, and there were tons more that we popped into just to take a look, but didn’t have the full time to stay.

One great thing that I enjoyed when navigating around Chicago is that many of the restaurants are located in specific areas. So, like many people do in the city, if you’re walking, you can find yourself essentially “window shopping” for which restaurant you may want to eat at during that time of day.

Whether you’re looking for a place to eat during brunch, lunch, dinner, or late night eats, Chicago is a place where you’ll be able to find exactly what you’re looking for and places that will meet the palettes of the people you may be traveling with.

Extra note – Even though I traveled with my girl group on this trip, I did take a look at the kid’s menu and I will say that each restaurant we visited had great options for the kids as well.

Tour PILSEN

While in Chicago, I highly recommend doing a walking tour. You can get access to a tour guide aka a Chicago Greeter and get a walking tour of specific areas for FREE. Yes, for free. No charge. You can get a customized tour based off of your interests to see architecture, family fun sites, or even a foodie tour. It’s up to you.

We had the privilege of getting a very unique, historic, and mural filled walking tour of Pilsen with our Chicago Greeter where we learned about the thriving culture of Pilsen. With so many murals which made it great for photos and learning about the history, we found unique little places where we learned things about Chicago that we would have never learned from a history book or even looking on Google.

A tour with a Chicago Greeter is something that I highly recommend doing especially if you’re wanting to fully experience the city.

Touring Pilsen was simply an experience that I’ll never forget and one that I’m excited to share snapshots off.

One of the things that is a must-do in Chicago is taking a cruise along the river. I recommend taking the architecture tour with Chicago’s First Lady Cruises which will take you on an extensive tour along the river giving you insight on the architecture of the city and giving you views that you won’t see anywhere else.

The 90 minute cruise is scenic and relaxing. You can sit along the upper deck and listen to the guide while seeing all of the buildings and monuments of the city along the river. If you’re not one to sit at the top deck, you can also enjoy the tour from the front of the boat as well as in the indoor setting where you can also purchase snacks and drinks if you choose to.

We also discovered that this river cruise line also offers the ability to charter a boat if you choose to for an event. During our cruise, we saw a wedding reception taking place on the the cruise, and I’m sure those photographs are going to be ones that people will be envying for years to come.

Chicago’s Art Institute is one to marvel. Even as a native of Philadelphia, and we have our own Philly places that you must visit with one being the Philadelphia art museum, Chicago’s Art Institute was immaculate, extravagant, and breathtaking.

I am not one of those people who can stare at art and look at the intricacies and point out the certain aspects of an era, but I am a person that can appreciate the work that an artist puts in and the meaning behind something. Going through the different exhibits to see the various time periods and cultures displayed was something inexplainable.

Our group originally didn’t think that we would spend much time in the institute but found ourselves wandering around so much that we ended up being in there for over two hours because there was so much to see.

It was also quite special to be able to see the Obama portraits. To see their story, the stories of the artists, and to see the portraits themselves right in front of me was an experience that I recommend for everyone.

If you don’t go to the Bean while you’re in Chicago, can you really say that you experienced Chicago. Though many people go to Millennium Park for the Bean, the park is way more than just that ginormous silver bean that it surrounded by people when you get there in the middle of the day.

At Millennium Park you’ll also find great landscape design, Cloud Gate, Lurie Garden, and various other hidden gems throughout the park that are great for pictures but even greater for finding places to relax and enjoy the city atmosphere.

If you’re planning on visiting the park to get pictures around the Bean then I highly suggest getting there between 7-8 AM. It gets quite packed very quickly and you’ll find yourself either waiting for a very, very long time to find a place to get only a few people in your background, or you’ll end up having to Photoshop a lot of people out if you have the ability and knowledge to do so.

Getting to the park early also has it’s perks for being able to explore the park without it being too crowded and loud. When a few of us from the group went early, we were able to see other places around the park that we probably wouldn’t have even gone to look for if it was too packed.

It’s no surprise that Skydeck is on this Chicago travel guide, because it’s an iconic place that you have to go to get that iconic city scape photo. When visiting, you’ll walk into a building where you may not be quite sure that you’re at the right place. You’ll go down two floors to find yourself checking in to the immersive experience.

We were happy to discover that Skydeck isn’t only going up to the top of a building and taking these photos and checking out the view, but you’ll also find yourself in an immersive experience where you’ll learn about the history of Chicago and find miniatures of iconic spots around Chicago.

Once navigating through all the photo opportunities, you’ll head up to the top floor and tour around the top of Skydeck to then wait in line for the Ledge. Keep in mind that when you’re heading up to take pictures on the Ledge that you won’t have tons of time. Each person or group is limited to a maximum of 2-3 minutes to be prepared with what type of photo you would like to take and also make sure to take a moment to appreciate the gorgeous view of the city.