Traveling with teenagers can be a challenge. At this age, the last place most of them want to be is with their parents or their family. They enjoy sleeping, a lot, so getting the day started may take a lot longer than you would like. It requires something very exciting to get their attention and Chicago has an amazing number of things to do that will fit the bill. Play it up before you leave home, make it seem exciting. Let them have some say in what you will be doing but refuse to let them dictate the entire trip.
Depending on where your home is your teen may never have traveled by subway or taxi. This may be enough to get their attention. Chicago has a great subway system and you will be using it to get in from either Midway or O'Hare airport. Traveling by cab is a bit of a luxury but the ability to get from one place to another quickly will keep your teen from totally losing interest.
You will have to use your knowledge of your particular teen to determine which of these suggestions will fit their personality best. The Willis Tower (former Sears Tower) is an experience that can get the heart of even the most blase teen pumping. It is exciting and nerve-racking at the same time, and the elevator alone is guaranteed to get their attention. Once you reach the top, 110 floors above the ground, you will be treated to views over 1300 feet below that will take anyone's breath away.
Rent a bike and hit the bike trails. Yes, they will complain but be firm and you will have a great time riding along the Lake Shore and enjoying Chicago from a different perspective. There are even guided bike tours if you prefer a little help. If you don't have any children under the age of twelve with you, head to Millennium Park and rent a Segway. This is a fun way to see some of the sights; can you imagine your teen saying no to taking a Segway Tour?
Chicago has some really beautiful beaches and this may just be a great way to spend an afternoon if you are visiting in the summer. Then head over to the Navy Pier and enjoy some of the activities there. You can grab a bite to eat, take a Ferris wheel ride or just look at all the great things that they have pulled out of Lake Michigan.
What teen doesn't love to shop? Take a walk down Michigan Ave and let them pick a few stores to poke around in. All the major retailers have outlets here and you can even do a little dream window shopping at some of the really high-end designers.
Try to find some kind of a show to take the teens to. Depending on what is available this is usually some sort of Broadway entertainment. You will need to check before you arrive what is being offered. Try to find something that might be of interest.
The Field Museum is one of the premier museums of Natural History and Science in this country. I was surprised at what will entertain a teen but certainly Bushman the stuffed gorilla will get their attention. When we visited, the Tut exhibit was being shown and of course, that is gone but there are always temporary exhibits that will keep the whole family happy.
One place we take our teens no matter which city we visit is the Hard Rock Cafe. Chicago, of course, has one and there is always plenty of food to appeal to the picky teen appetite and lots of noise to drown out any whining that is going on.
If your teen likes a challenge, take them to Chinatown and introduce them to dim sum. Learning to use chopsticks and eating ethnic food will broaden their horizons and appreciation of other cultures.
You will want to make sure that you try Chicago deep dish pizza at least once. There are great places to do this all over town.
Chicago has plenty of sports teams and if your teen is a sports fan you can make the attempt to get tickets before you leave home. These teams are very popular with their local fans so get your tickets as much in advance as possible.
When it comes to hotels one of the suite hotels is a good option, something like Embassy Suites or Residence Inn are good choices. Not only do they include breakfast but they allow your teen to have privacy and as a result, you get a little privacy yourself. Privacy, it's a good thing!
Visiting Chicago with teenagers can be a lot of fun, these are just a few suggestions of things to do, and there are literally hundreds more.