Meg Thomson
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Best Places to Go on Your Road Trip to Chicago

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Chicago, IL

Chicago, Illinois, is positioned right on Lake Michigan, making it the perfect destination for your next road trip.

When you’re driving into the city, one of the first things you’ll notice is the skyline. If you take the Chicago Skyway (a toll road, but definitely a fun experience), you’ll experience another incredible view. Take Lakeshore Drive into the city and you’ll be able to drive right along the water, with sandy beaches and the hustle and bustle of boardwalks.

If you’re planning a road trip to Chicago, you’ll also want to plan where you’re going to go. Driving aimlessly doesn’t work well in the city, so you’ll need a plan. Here are a few must-see places you’ll want to check out.

See the City: Chicago, Illinois

The Beach

There are plenty of beach access points throughout the city of Chicago. If you’re looking to see the water with the hustle and bustle of other tourists, try taking Michigan Avenue up the Chicago River to see where it opens into Lake Michigan. If you’d rather avoid the more intense crowds, the northern parts of the city offer more open beach areas, including Leone Beach Park near Loyola University.

Michigan Avenue

If you’re looking to shop while you are in the Windy City, Michigan Avenue is the place to do it. Nicknamed “The Magnificent Mile,” the most famous section of Michigan Avenue stretches through downtown, decorated with upscale shops and restaurants. In the heart of Chicago, you really can shop ’til you drop.

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The Willis Tower

Many still refer to this building as The Sears Tower, but its name was changed in 2009. Completed in 1973, the Willis Tower held the title of the Tallest Building in the World for 25 years. Today, the Willis Tower is the tallest building in the United States. The building is 110 stories tall and features the well-known Ledge in the Skydeck. The Ledge is a bay made entirely from glass that protrudes out of the 103rd floor of the building. Visitors can step out into the glass box and look down at the 103-story drop, as well as a breathtaking view of the city. In fact, on a clear day you can see four states from the top of the skyscraper: Illinois, Indiana, Wisconsin, and Michigan.


If you’re looking to simply explore the city, a great place to start is the Riverwalk. The Riverwalk, located on the Chicago River, offers beautiful sights of the city and its waterways. Passersby can admire the architecture and natural beauty of the river. River taxis and boat tours will take you up and down the water; there are even architectural tours available if you are interested in the city’s buildings.

Navy Pier

Navy Pier is one of Chicago’s most visited landmarks with more than 9.3 million visitors in 2016. Last year, Navy Pier celebrated its 100th anniversary. The infamous Ferris wheel, known as the Centennial Wheel, stands at nearly 200 feet tall. From the top, riders can have a full view of both the city skyline and Lake Michigan’s horizon. At Navy Pier, visitors can also enjoy things like cruises, museums, and delicious food festivals.

If you’re planning a road trip to Chicago, make sure you plan your route and your destinations accordingly. Driving in the city is a bit hectic, so it’s good to know where you’re going.

Sources: Willis Tower, Navy Pier