When planning a road trip, remember that everyone in your family have their own interests. It is best to plan at least one attraction or activity each family member wants to do, especially if you have children of different ages.
Milwaukee offers a lot of things to see and do for the whole family. Start your road trip with a treat for the young ones. Betty Brinn Children's Museum is particularly built for children under ten as it houses different themes such as Curious George along with their all-year kiddie exhibits. As a treat to the teens, take the family for a Harley-Davidson experience. Enjoy an hour free tour and learn how those big Harley bikes are made. It will be best to end the day with something everyone in the family could all appreciate -- a basketball game! Head to the Bradley Center and catch the Milwaukee Bucks in action in their home court before checking in at the Ambassador Hotel for the night.
Note: If you plan to take the road trip in the summer, the Summerfest at the Marcus Amphitheater is something you should not miss. It is a big annual musical event that lasts eleven days. Everyone in the family can get in at a very cheap price (and kids under three can get in for free).
Start early the following day for the four-hour drive to Indianapolis. Visit the Indianapolis Zoo and White Water Gardens. At the zoo, your family gets to meet hundreds of wild and backyard animals. The White Water Gardens is a unique glass building that celebrates Midwest gardening. The grounds are perfect for parents to relax and allow their kids run around. Head next to The Greatest Spectacle in Racing, the Indianapolis 500. Feel the atmosphere of NASCAR race and enjoy the speedway all for yourselves. Before finally driving to Chicago, take a break from your road trip with a meal at Capital Grille and a good rest at the Indianapolis Travelodge.
Drive a little more than 180 miles to your main destination - Chicago! The Windy City has lots of attractions and activities waiting for your family to enjoy. Before exploring the city, see all of Chicago from its tallest building, the Sears Tower Skydeck. Enjoy having the bird's eye views of the entire city, Lake Michigan, and the surrounding suburbs. On a clear day, you can even see parts of Indiana, Wisconsin and Michigan. Designated drivers can take a break from the wheel for a while by taking an open-air Chicago Trolley Tour led by a knowledgeable and entertaining guide. The tour takes frequent stops to museums and other top attractions for visitors to fully explore Chicago, and even a meal at the Rainforest Cafe or other nearby restaurants. Take the family to see some more animals - mostly aquatic ones this time - at the John G Shedd Aquarium. Join an entertaining crew on a Wacky Pirate Cruise loaded with fun that is sure to delight both parents and kids. Conclude your road trip with a stroll at the Chicago Park District at dusk where you get to unwind and enjoy nature in the midst of a busy city.