Lake Shore Drive
Chicago’s grand lakefront highway is obviously a tremendous place to start. Stretching over 15 miles from Jackson Park to Edgewater, LSD is easily Chicago’s most picturesque ride. With traffic at record lows these days, there is hardly a better time to enjoy the drive. It’s not only traffic that’s missing from the lakefront, though: warming temperatures usually brings Chicagoans by the thousands to the adjacent Lakefront Trail and beaches. Seeing as these areas are closed for now, a cruise down LSD is essentially the closest you can get to the lakefront.
Bluff Rd., between Lemont and Romeoville
Who says Chicagoland isn’t hilly? A stretch of this small road about two miles long between Lemont Road and Joliet Road is a local gem. It cruises along the side of, you guessed it, a bluff, and offers a great view of the adjacent Goose Lake and Des Plaines River. As the road and views are unlit, this one is definitely best enjoyed between dawn and dusk.
Sheridan Rd., north of Winnetka
The North Shore has its own answer for hilly and windy roads in a famous stretch of Sheridan Road. Heading northbound, around Tower Road in Winnetka is where things start getting interesting. Through many curves both soft and abrupt, you’ll wind your way through beautiful forestry and homes in a handful of communities along the way. It’s easy to get carried away, especially as Sheridan continues over 40 miles to the north into Racine, Wisconsin.
Ever notice certain large Chicago streets that are flanked by green space on both sides, with homes set back significantly and accessed by smaller service roads? You’re probably on the city’s historic Boulevards system, an interconnected inner ring of such streets that wrap almost entirely around the city, connecting many notable parks along the way. It begins along the famous Midway Plaisance at the University of Chicago’s campus and continues to the west and north, connecting Washington Park, Gage Park, McKinley Park, Douglas Park, Garfield Park, Humboldt Park, and Logan Square. Conceived by a developer to raise property values on what was then the outskirts of the city, it began construction in the 1870s and remains not only a beautifully coordinated system, but a fascinating cross section of dozens of diverse communities.
Thatcher Ave., between River Forest and River Grove
Many streets run through the Cook County Forest Preserves, but this stretch of Thatcher Ave. is particularly pleasant. Some parts divide quiet residential areas from forest land, while others are wholly surrounded by woods. It also provides easy access to the Jerome Huppert and Thatcher Woods, as well as the Des Plaines River Trail.
Stony Island Ave., near Lake Calumet
When you think of scenic drives in the city, what comes to mind first? Perhaps Lake Shore Drive or vibrant neighborhood corridors? It certainly isn’t this stretch of Stony Island, which few people ever have reason to take as it’s arguably the sparsest area of the entire city. But take it you should, as you’ll find a stunning expanse of desolate prairie right in the city. You’ll also find Big Marsh Park, a massive park known for biking, hiking, and even bird watching.