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6 Reasons Chicago Should Be Your Next Unexpected Family Vacation!

We found all the family fun in Chicago, and now, I'm here to tell you about it!

By Kara Guillard, Macaroni KID Youngstown September 8, 2023

When you think of your next family vacation what do you think about? Beaches? Rides and thrills? Museums? Great food? What if I told you there was a place within a six-hour drive nearby that you might not have considered that has all of the above? I recently had the pleasure of exploring the Windy City of Chicago with some of my fellow Macaroni Kid publishers. I, as you might be, started out wondering if Chicago could really be a trip for the whole family, and now, I'm already planning my trip back, this time as a Family Vacation! Why you might ask? Here are my top reasons for visiting Chi-town with your family!


The author was hosted by Sheraton Grand Chicago Riverwalk, Blue Man Group, and Chicago CityPASS® to facilitate writing this article. All thoughts and opinions expressed are their own.



Right outside the back entrance of the Sheraton Grand Chicago Riverwalk.

1. Sheraton Grand Chicago Riverwalk
When I first arrived in Chicago, I was in need of some luxury! After six hours in the car, I was ready to stretch out my legs, relax and snack. I was able to easily park my car in the Sheraton Grand Chicago Riverwalk’s underground parking and ride the elevator right up into the lobby. Check in was a breeze and came with a free bag of Chicago mix  popcorn (caramel corn mixed with cheddar corn!)

The convenience of the hotel really made my trip a relaxing one, being just a short walk away from many attractions, including the Riverwalk which can be accessed from the back entrance of the hotel! The food options just inside the hotel were plentiful, although I could’ve lived on the pastries from the cafe alone. If the convenience and the free popcorn doesn’t seal the deal, the amazing views from your hotel’s window definitely will!


2. Blue Man Group
This was my first experience with seeing Blue Man Group, so I didn't know what to expect. The show was full of comedic artistry that is sure to have something for everyone! As soon as the trio walks on the stage you'll be laughing, impressed by the unconventional ways they make art and blown away by the live musical performances (and the "instruments" that are used!

Blue Man Group is a must-see if visiting Chicago! Just be prepared to possibly get a little messy if in the first few rows and that audience participation is a big part of the show. From the crowd around me, I could tell this is a show people go to again and again. At the end of the show you even have the opportunity to purchase some of the art that they make on stage, could you imagine a better souvenir? 




 





3. Skydeck Chicago
My favorite part of Chicago? The views! So what better way to soak in and appreciate the architecture of Chicago than at 103 floors up, standing on a see-through platform so you can see everything below your feet? Some might say - no, that's not for me, but the sights are breathtaking! No need to worry, if this part of the tour isn't for you, you can skip it and still have an amazing time at Skydeck Chicago. The Skydeck has many beautiful views with your feet on the floor, an area with fun photo ops (like a giant Chicago Pizza!), and lots of information about Chicago and the Willis Tower! This is just one of many attractions available with Chicago CityPASS®.


4. Chicago CityPASS®
So what is the CityPASS® and why was it one of my favorite parts of visiting Chicago? When I go on vacation I am all about two things: saving money where I can to get the most out of my vacation and making things as easy as possible on myself so I can enjoy more and stress less. Chicago CityPASS® read my mind! You pay for only TWO attractions and get access to FIVE of Chicago's biggest attractions! The app made the experience even better because I was able to easily book my reservations, or cancel and reschedule if I realized the time wasn't going to work for me. I was able to visit the Skydeck Chicago, Shedd Aquarium, Art Institute of Chicago, 360 CHICAGO Observation Deck and the Shoreline Sightseeing Architecture River Tour and none of them disappointed!



The Shoreline Sightseeing Architecture River Tour, an attraction on Chicago CityPASS®.


5. Navy Pier
A short walk from the Sheraton Grand Chicago Riverwalk is the Navy Pier. The Pier is beautiful and free to walk on so it's definitely worth stopping by. From the pier, you can see Lake Michigan, visit some restaurants and shops, ride a few rides (including the nearly 200-foot tall iconic Centennial Wheel!) or just sit, relax, and take in the view. Throughout the summer you can also catch fireworks every Wednesday and Saturday.

There is plenty for kids to do on the Navy Pier including Chicago Children's Museum, Amazing Chicago's Funhouse Maze, a giant splash pad at Polk Bros Park, amusement rides, and more! Throughout the year, you can also catch public performances and shows at the Pier. It's safe to say there is something for everyone at the Pier and a must-see if visiting Chicago.


6. Museums, Museums, Muesuems!
While walking around Chicago, I noticed what was not in short supply - museums! Every corner seemed to have one, and if you couldn't find a museum you could still find a bit of history everywhere you look. From ice cream, to science, to children's museums, if you're looking for an educational - as well as a fun - trip, it looks like Chicago could be THE destination.



The Navy Pier from afar.


When I think of a family fun vacation, Chicago wouldn't have been a location I would've considered. Now, I am already planning out when to go back with my family. An easy six hour drive from Youngstown, Chicago is close enough for an extended weekend trip or a week long trip. I spent three days exploring Chicago and still felt like I barely scratched the surface of everything there is to do and see there. On a return trip I am already planning on visiting the parks and stopping by the free Chicago Zoo. If you are looking for a family vacation that is fun, educational and breathtaking, add Chicago to your list, you won't be disappointed.