Experience the Breathtaking Chicago Skyline on Lake Shore Drive Road Trip Route

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Friends riding in a car, smiling

Travel Guides Road Trips

 Lauren Richards



Chicago is a lively city with a fantastic food and arts scene. It has majestic skyscrapers and a multitude of green spaces, making for a beautiful blend of concrete and nature. It’s situated right along Lake Michigan, giving its inhabitants access to lovely views and beach activities. No matter what your interests are, you’re likely to find something that piques them in this city of over 2.6 million people.

One way to take in its beauty is to drive through it. Chicago does have its traffic, don’t get us wrong, but it’s worth sitting through when you hop on the iconic Lake Shore Drive. The nearly 16 mile parkway brings some spectacular views of the city skyline. You can drive it during the day and see the buildings towering over the lake and note all the varying architecture, or you can hit the road at night and see the city lights twinkling as you blitz underneath them. Whichever you decide to do, it will certainly be magical.

A brief history lesson, plus some stops to make

Aerial view of Chicago

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Lake Shore Drive, sometimes called LSD by locals, was named and built in the 1880s, according to the Chicago Public Library. It started off as a road that was only a half a mile long and slowly grew, both in length and popularity. Now, North Lake Shore Drive is one of the busiest streets in the city. In 2021, it continued to make history by getting a name change. It went from simply Lake Shore Drive to Jean-Baptiste Pointe DuSable Lake Shore Drive to honor one of the city’s founders.

In addition to a fascinating history, it also has fascinating attractions to visit along the way. Some of Chicago’s most famous tourist spots, like Navy Pier, which regularly hosts events and activities, and the Chicago Bears’ stadium, Soldier Field, are quite close to an exit. If you’re itching to get out of the car, you can find a space to park and continue on Lake Shore Drive by walking along the Lakefront Trail.

More stops along the way, and the best times for travel

View of Lake Shore Drive


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Other fun stops include one the best museums to visit in Chicago, the Museum of Science and Industry and the McCormick Bird Sanctuary. You can experience Chicago by making a full day out of the drive by spending time at each of these mentioned stops. Some, like the museum and Navy Pier, will take up more time than others, so make sure you plan accordingly and visit your top choices first.

Like we mentioned earlier, traffic along Lake Shore Drive can be heavy. However, you can easily plan around it, since the rhythms of the road are relatively consistent. According to Rosenfeld Injury Lawyers, the best times to hit the road are prior to 6am — if you want to see the skyline at sunrise, this is a great time for that — after 8am but before 4pm, and then again after 6pm. Essentially, if you want to avoid traffic, avoid traveling at rush hour.

Next time you’re in Chicago, or if you’re searching for a place where you can enjoy city life and a scenic drive, pencil a ride along Lake Shore Drive into your plans.

Dave Pennells

By Dave Pennells

Dave Pennells, MS, has contributed his expertise as a career consultant and training specialist across various fields for over 15 years. At City University of Seattle, he offers personal career counseling and conducts workshops focused on practical job search techniques, resume creation, and interview skills. With a Master of Science in Counseling, Pennells specializes in career consulting, conducting career assessments, guiding career transitions, and providing outplacement services. Her professional experience spans multiple sectors, including banking, retail, airlines, non-profit organizations, and the aerospace industry. Additionally, since 2001, he has been actively involved with the Career Development Association of Australia.