The Ultimate Chicago Travel Guide

Location: United States, East Coast,
Chicago Theater Scaled


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.


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While in Chicago, a great place to stay is the 21c Museum Hotel in Chicago. This hotel is one of the newest hotels in River North and as soon as you walk in, you almost forget that you are staying in a hotel because of the contemporary art exhibits that are present on the first and second floors. The room is super spacious and in the double bed room that we stayed in, there was also a couch / work area and out of the window we had a great view of the city. One aspect that I thought was super convenient was how centrally located the hotel is. We visited many places while we were in Chicago and, as many know, Ubers and Lyfts can be expensive, so being able to walk to many of the destinations was a big perk. It only took us 10-15 minutes to walk to big destinations such as the Riverwalk and to Millennial Park.
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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.

Pilsen Yards Chicago Brunch


    If you’re traveling to Chicago, you’ll want to get yourself a deep dish pizza. Lou Malnati’s is a well known location for getting a classic deep dish. There are multiple locations around the city, and I highly suggest to make a reservation because it can be super busy. When ordering, prepare yourself for a lot of food. We ordered a large pizza for four of us and ended up only eating half because it is so plentiful – granted, we also had a salad to start since the pizzas are made fresh and can take up to 45 minutes to reach your table, so be prepared for that.
    Pilsen Yards (located in Pilsen) is an open air bar-centric restaurant that you’ll find comfortable and relaxing, and you’ll end up not wanting to leave. The restaurant is open for brunch through dinner and serves Latin inspired street food. I can also say that their cocktail menu is quite impressive and I tried quite a few drinks and was not let down by any of them. I highly recommend getting the french toast is you visit for brunch, and if you’re heading their for late night, Pilsen Yards also has a hidden gem – the Alderman – which is a speakeasy side bar that you’ll probably want to spend you’re whole night there.
    The Girl & the Goat is another place you’ll want to eat while you’re in Chicago. It is one of a few restaurants owned by one owner in the area with a central naming theme that you’ll see. This restaurant serves food family style, so be prepared to order multiple plates and share. We ended up ordering about 8-12 plates for the five of us and though we did end up super full at the end, we didn’t regret one bite. You can find everything from oysters to braised beef on the menu which makes this a great restaurant to eat with a group of diverse palettes.
    As mentioned, Chicago is a city of surprises including the Miami-like beach that is easy to navigate to when you’re in the city. The Shore Club is one of the restaurants located at the beach and it’s name speaks for itself. You can enjoy and upscale dining experience on the inside of the restaurant and enjoy the atmosphere and a variety of fresh bites, or you can head outside to the cabana area and enjoy bites, drinks, and entertainment.
    I’m a lover of sushi and Asian fusion food, so Sunda was right up my alley. This restaurant also does family style dinner where you can order a variety of plates and get the tastes of many different types of food. The plates here are on the medium side so for a group five, we ended up ordering about 6-7 plates and we were quite full. We actually didn’t end up finishing all the food and took some to-go, so you won’t be disappointed by the portion size. I highly recommend getting a platter of sushi, spicy edamame, and the fried rice.

I’m always one that says when you visit a place to make sure you eat the food that the location is known for. And even though Chicago is known for the deep dish, I will say that Chicago is an eclectic city that is diverse, artistic, and has food that you’ll want to try as soon as you catch a whiff of the food floating through the air. These restaurants are ones that you’ll want to put in your itinerary when you’re making your plans to visit Chicago, and if you happen to be a native of the city and haven’t visited these places, I highly recommend that you do so!

The Oasis At The Shore Club Chicago



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.

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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.

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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.

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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.

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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.

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READ the Travel Guide of the Babes That Wander

Ultimate Chicago Travel Guide for a Summer Girls’ Getaway by Lauryncakes

Chicago Itinerary & Guide: How to Spend 2 Days in Chicago by Miss Moore Style

Girls Trip to Chicago: a Complete Weekend Guide by Greta Hollar

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Skydeck Immersive Experience



Chicago Travel Guide
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