Plan an Awesome Chicago Getaway with Your Teen | Wisconsin Mommy (2024)

Living in Wisconsin, we are lucky enough to have pretty easy access to Chicago. Whether we drive down or take the train, we love to spend time in a city that offers so many different things to do. Josh and I snuck down for a few days during his spring break and had a great time. Of course, visiting a city with a teen is a bit different than visiting with little children or your spouse. Making sure your teen has a great time in your Chicago getaway is easy with a little planning.

First, stay at a really cool hotel.

We all know that a big part of the fun on any getaway is the accommodations. I wanted to stay at a hotel that had more character than a typical “business hotel” chain but also offered great service and a convenient location. I immediately thought of Virgin Hotels right on Wabash Avenue and they were kind enough to agree to host us. (I had stayed there on a previous business trip and immediately fell in love with Virgin’s cool vibe!)

While Virgin Hotel impresses me with its superior customer service (I’ve been obnoxiously early on both visits and was happily issued a room key upon arrival), reassuring security (the elevator will not go up without a room key card), and upscale amenities, my teen was particularly enthralled with the decor. The signature Virgin red is very prominent in the decor and lends a classy feel to every corner of the hotel. I was anxious to show Josh the second floor Common’s Club as it has tons of bookshelves filled with quirky knickknacks that were reminiscent of any 70’s childhood.

Our room (or “chamber” as they like to call it) was spacious and very comfortable for the two of us. Josh immediately fell in love with the dog chained outside our door and the vintage-looking fridge inside the sleeping area. The room had a high-tech feel which he loved. All of the controls can be directed by an app (Lucy) which he declared “very cool” and many of the lights were motion activated. Since, like most teens, the mini-bar food selection was the first thing he saw, I was thrilled that the prices were typical to what you would pay at the local convenience store and even let him sample a few items.

We both loved that Virgin Hotel is located just a quick 10 minute walk from Millenium Park as that is another must do when in Chicago! I also loved the convenience of having a coffee shop, Two Zero Three, right adjacent to the lobby and a delicious restaurant, Miss Ricky’s, on site as well.

If you are looking to score some “cool points” by staying in a hotel that will impress your tech-savvy teen, I highly recommend Virgin Hotel!

Next, get a CityPASS.

I had never really looked into CityPASS before. We have several museum memberships that have reciprocal agreements with some of the Chicago museums so we had alway’s stuck with those. I was given a Chicago CityPASS to try out and thought this trip would be a good opportunity to see what all the rave reviews were about.

First of all, let me point out that CityPASS has some really cool perks that you don’t get with a regular attraction ticket or reciprocal ticket (beyond just the 53% savings on ticket prices). While the lines were not too long just yet, the VIP entrance to the attractions we visited was a really nice touch! We had a limited amount of time in the city and definitely did not want to spend it in lines. We also had the chance to “add on” extra experiences at the museums for no extra cost. We added things like 4D movies and animal shows that we might have skipped if we’d had to pay extra for them.

The Chicago CityPASS offers

We took advantage of the Shedd Aquarium, Skydeck, and Museum of Science and Industry. Since we only had two days, we weren’t able to visit the Field Museum or Planetarium which Josh would have loved to do. Don’t worry though, you have nine days to use your entire booklet, so if you are in town longer than we were you can hit all of the attractions.

You can purchase your CityPASS booklet ahead of time and just present the mobil app at the first attraction and you will receive your physical booklet at that time.CityPASS has a 98% customer recommendation rating and it’s easy to see why. Chicago CityPASS costs $99.75 for adults (value $212) and $84.75 for kids ages 3-11. You can learn more at theChicago CityPASS Website.

I guess the biggest test of how much I like something like CityPASS is whether I would purchase one for another city I visit and the answer is a resounding YES. CityPASS has booklets for Atlanta, Boston, Chicago, Dallas, Houston, New York, Philadelphia, San Francisco, Seattle, Southern California, Tampa Bay and Toronto. I may make it a personal goal to use one in every single city listed!

See Blue Man Group

I’m lucky that my teen shares my love of theater and is usually pretty willing to go see whatever musical I am currently obsessed with, but you don’t have to have a theater-loving teen to enjoy Blue Man Group. It is a show unlike any other I have ever seen (and I’ve seen a LOT of shows!) and we were grateful to have been invited to review it. There were several high school classes in attendance at our performance and they all loved it as well, so I feel pretty safe in saying just about any teen will enjoy the show. (It is actually recommended for ages 3 and up.)

Photo Credit: Lindsey Best

If you aren’t familiar with Blue Man Group, it’s been around since 1991 and cleverly combines music, technology, comedy and performance art. I had seen video clips of the blue men banging on paint splattered drums and thought that was what the majority of the show consisted of. I was thrilled to find that while drumming is part of the show, it really goes much deeper than just drumming. The blue men poke playful fun at our everyday lives and culminate the experience with an interactive dance party.

Photo Credit: Lindsey Best

Tickets are available from $49-$99. Tickets may be purchased at the Briar Street Theatre by calling the box office at (773) 348-4000; by calling Ticketmaster at (800) 982-2787; at all Ticketmaster ticket centers or via the Internet.For a full show schedule and ticket pricing, please the show’s website. Special rates are available for groups of 10 or more, varying from $46- $69 per person. For groups of 10 or more, call the group sales department to book at: 773.348.3300 or email to request information.

Visit a candy store.

You may think of young kids when you think of candy but the look on my teen’s face when we walked into Dylan’s was priceless. Two full floors of nothing but sugary goodness. He was in heaven and I scored some cool mom points.

Last, make sure to check out Navy Pier and Millennium Park.

I hadn’t been to Navy Pier in quite a while and was surprised at how many changes had taken place. Navy Pier is currently under construction, so more changes are on the way. We had fun walking around and checking out the shops and sampling some of the delicious food offerings. We even took a quick jaunt through the funhouse maze and admired the stained glass collection at the Driehaus Gallery of Stained Glass. Josh was amazed at the detail and layering in the glass. Be sure to grab a souvenir at Best Gift Idea Ever to hang on your wall when you get home!

We always made Millennium Park a stop on visits when Josh was a toddler since he loved splashing in the fountain (it’s allowed!). Since he is a budding photographer, he loved the chance to snap some beautiful pictures of the Bean and all of the flowering trees and plants. It was just a short 10 minute walk from our hotel and gave us a chance to enjoy the beautiful weather.

We’ve enjoyed visiting Chicago ever since Josh was a toddler, but planning a Chicago getaway with a teen is whole new experience for us and we had an absolute blast! These are only a fraction of things for teens to do in Chicago and we can’t wait to come back down and explore even more!!

Plan an Awesome Chicago Getaway with Your Teen | Wisconsin Mommy (2024)
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