The Windy City is one of my favorite places to visit! Are you planning on visiting Chicago with teens? If so, I’ve complied a list that is sure to please even the pickiest teens.

Skydeck

The Skydeck in Willis Tower is an awesome experience!! It’s not very often you get the chance to stand on a glass floor and look down 1300+ feet! Located on the 103rd floor and the whole floor has amazing views of the city!

It’s the 2nd tallest building in America at 110 floors. The Skydeck IS the tallest observation deck in America!

The Ledge’s glass boxes extend out a little over 4 feet and they can hold 10,000 pounds!! Definitely strong enough to hold you and your fam!

There are several ledges with different views. A couple of them are set up to where you take your own photo and one is set up to take your photo. The photos are a little pricey. No matter which ledge you choose, count on long lines. It’s worth it!!

Millennium Park

This park is home to the famous Cloud Gate sculpture…..AKA The Bean. The iconic sculpture that represents Chicago. Teens will love taking selfies and posing in front of this mirrored piece of art.

The park itself is 25 acres and holds a huge amphitheater with the coolest looking design!

The Crown fountain is located here as well. It has two tall media displays picturing the people of Chicago. Water shoots out of their mouths! Smaller kids will love playing in the water, but the older ones will still think it’s cool to check out.

Navy Pier

This is one of the most popular tourist destinations in Chicago. Located along Lake Michigan, it is home to multiple amusement park rides, restaurants, shopping, a children’s museum, an IMAX theater and multiple city cruise departures.

The huge Ferris wheel on Navy Pier is called Centennial Wheel. It opened since the last time we were here, so we haven’t had a chance to ride it yet. We did ride it’s predecessor and loved it. This one is 50 feet taller making it 200 feet tall! Plus, it’s climate controlled!! Huge plus in the winter! This offers some of the best views of the city.

This is the previous Ferris Wheel.

Magnificent Mile

Located on North Michigan Avenue is the some of the best shopping in the country!! It’s over a mile long with shops, flagship stores, restaurants, and malls. If your teen likes to shop, they will be in shopping heaven! Boosts over 400+ stores, 200+ restaurants and 50+ hotels.

Dylan’s Candy Bar

This is the biggest candy store I’ve ever visited!! It’s on Michigan Ave. and definitely worth a stop. Think your teen is too old for this, think again. It’s two floors of sugary yumminess!! It’s sure to be a hit!!

Museum Of Science and Industry

This is one of the best museums we’ve ever been too!! That’s saying a lot since my teens dislike most museums! It’s one of the biggest museums we’ve ever been too as well! You need a full day to really experience it. Maybe even a couple days if you want to see everything. Some of the exhibits include a U-505 Submarine, Coal Mine, Chick Hatchery, an amazing train display, transportation gallery and so much more!! Highly recommend!

Theatre

Chicago is known for hosting phenomenal musicals, comedies and Broadway shows. If your teen is into the theatre scene, it is a MUST do! See a show at the iconic Chicago theatre or maybe Shakespeare in the Park!

Blue Man Group

I’ll be honest with you, I haven’t seen them…yet! I do not normally recommend things I have not personally experienced. However, I’ve read multiple reviews and have heard friends rave about this show!! I will be shocked if you don’t walk away loving this. And it’s on my bucket list, so I’ll update this with a personal review as soon as I see it.

Deep Dish Pizza

Chicago is known for it’s delicious deep dish pizza! You must try it!! We ate at a few different pizza places to try and find the best one. Honestly, they are all good but our favorite is Lou Malnati’s!! Hands down! Runners up are Giordano’s and Gino’s East.

Baseball Game

We love going to baseball games and seeing Wrigley Field was awesome!! Even if you’re not a cubs fan (and we’re NOT), checking out the ballpark was a great experience! It was built in 1914!! I would love to take a tour of the place next time.

Chicago is a great place for a week long vacation or a weekend getaway with your teens. Definitely check it out! If you’ve been there before, what’s your favorite thing to do in Chicago with teens or without??

If you have younger kids, check out this post on the Top 10 Things to do in Chicago with Kids!

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