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The 9 most scenic drives in Chicago

See Chicago from your car window with these unexpectedly beautiful scenic drives in Chicago

By Morgan Olsen
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One of the undeniable draws of living in Chicago is that you don't actually need a car to get around—the city's vast public transportation system can ferry you from one side of the city to the other in no time. But even the most devoted city-dweller sometimes craves the opportunity to get behind the wheel and cruise through the city with the help of four wheels and an engine. When you must scratch that itch, consider these scenic drives one of the best things to do in Chicago as well as an opportunity to explore beyond your neighborhood. All located within city limits, these roadways will take you through Chicago parks, along the lakefront and through the heart of the city. Buckle up and hit the road on these scenic drives in Chicago.

Note: If you plan to get out of the car, remember to stay safe by wearing a mask and practicing social distancing. Call ahead to see if nearby businesses are open. 

Scenic drives in Chicago

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shutterstock, chicago, chicago skyline, downtown, downtown chicago, chicago river, bridge, loop, the loop, cityscape, skyline view
Photograph: Shutterstock

Wells Street Bridge

Connecting the Loop to River North over the Chicago River, this double-decker bridge is a postcard-worthy landmark for locals and tourists alike. The upper deck is lined with tracks for the CTA's Brown and Purple lines, while the lower deck offers three lanes of southbound traffic for cars. If you time it just right, you'll be cruising into the Loop with a CTA car rumbling by overhead. A quick glance out the passenger's side window will reveal the glassy city skyline.

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university of chicago, chicago, historic building, downtown, south side, shutterstock
Photograph: Shutterstock

Midway Plaisance

If you've ever been on the campus at the University of Chicago, chances are you've probably ended up on the Midway Plaisance, a mile-long bit of road that connects Jackson Park and Washington Park. There's plenty of lush green space sandwiched between the opposing roadways, and you'll be able to see the stately University of Chicago buildings off to the north. Continue west to loop around the DuSable Museum of African American History, or go east to wrap around the lagoons of Jackson Park.

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chicago, skyline, lake shore drive, lake, lake michigan, waterfront, city, shutterstock
Photograph: Shutterstock

Lake Shore Drive

Only in Chicago does the phrase "cruising on LSD" not raise concern. The abbreviation "LSD" stands for Lake Shore Drive, a stretch of road that hugs up against the city's eastern most border, separating our sprawling metropolis from Lake Michigan. Running from Edgewater to Jackson Park, the expressway offers breathtaking views of the skyline, notable institutions and—of course—aqua-hued waters.

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millennium park, skyline, grant park, city, downtown, shutterstock, bean
Photograph: Shutterstock

Columbus Drive

Cutting through Millennium Park and Grant Park before merging onto Lake Shore Drive, Columbus Drive is surrounded by green space and sightseeing landmarks. While you're coasting, you'll pass under the BP Pedestrian Bridge designed by architect Frank Gehry past Butler Field before you catch an unobstructed view of Buckingham Fountain and its surrounding gardens.

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Logan Square Boulevards

Encompassing parts of Humboldt Boulevard, Kedzie Avenue and Logan Boulevard, the "boulevards" of Logan Square are lined with some of the most stunning architecture in all of Chicago. Marvel at massive Victorians, stately brick homes and textbook examples of Prairie School style. The tree-lined streets and grassy picnic nooks that line the streets don't hurt the view, either.

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route 66, state street, illinois route 66, downtown, street sign, chicago, shutterstock
Photograph: Shutterstock

Historic Route 66

No doubt you've heard of Route 66, the iconic stretch of roadway that once ran all the way from Chicago to Los Angeles, spanning almost 2,500 miles. Though most of it's been dismantled and replaced by more efficient highways, there are still remnants of the historic path, including its start and end points in downtown Chicago. You'll find the "begin" sign on Adams Street, just west of Michigan Avenue; the "end" sign (for the portion of the road within in the city) sits near the intersection of Jackson Boulevard and Michigan Avenue.

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Lower Wacker Drive

Remember the scene in The Dark Knight where Batman, the Joker and a crew of cops face off in a high-speed chase beneath the city streets? That heart-pounding scene was filmed on Chicago's Lower Wacker Drive, located directly below Wacker Drive downtown (fun fact: There's even a third tier below that, known as "Lower Lower Wacker Drive." Though many Chicagoans will disagree about the street's scenic appeal, there's no denying that this iconic city shortcut feels like an entirely different world.

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humboldt park, humboldt, park, green space, outdoors, outside, nature, lagoon, water, beach, shutterstock
Photograph: Shutterstock

Humboldt Drive

When the weather is agreeable, Humboldt Park is buzzing with action—from folks walking the winding trails and sports teams warming up to swan boats gliding across the lagoon. You can see it all when you cruise through the center of the Park via Humboldt Drive; wrap around Luis Munoz Marin Drive to extend your trek before checking out the National Museum of Puerto Rican Arts & Culture.

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chicago, bridge, downtown, chicago avenue, city, shutterstock
Photograph: Shutterstock

Anywhere under the "L" tracks

When they visit Chicago, New Yorkers often refer to the CTA as the "subway," but city-dwellers know that many of the city's train tracks are actually above ground. In the downtown area, streets like Wells, Clinton and Wabash are shaded by these tracks, which sit just above street level. Beyond blocking the sun from our eyes, they cast beautiful, speckled shadows on the pavement below, creating an enjoyable and iconic path on which to drive. Just be careful not to run into one of the pillars!

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