Explore arguably Chicago’s greatest decade in sports, film and culture

Bike through Downtown Chicago and Grant Park, and hit all the pop-culture sites from the 80’s. Delve deep into the politics, personalities, and players that led and transformed Chicago during the 80’s decade when the Blues Brothers and Ferris Bueller took over Chicago streets and the Bears took home the Super Bowl trophy. 

Rent A Bike and Cruise Chicago’s Iconic Sites from the 80’s 

Grab an electric bike, comfort bike, road bike, kids bike, or whatever bike you fancy and hit the streets for an 80’s themed bike ride. The Bobby’s Bike Hike shop is conveniently located in the heart of Chicago’s 20-mile Lakefront Bike Trail at 540 N Lake Shore Dr. We offer free bike locks, helmets, and maps with all bike rentals. ONLINE RATES INCLUDE 10% DISCOUNT.

Bike Past These Downtown Chicago Sites for an Iconic 80’s Day Out

The Blues Brothers: Visit some of the most iconic spots from the movie and discover how it transformed Chicago’s relationship with Hollywood

Ferris Bueller’s Day Off: Life goes by pretty fast, but your biking pace can be leisurely as you ride in the protected bike lane that follows the parade route from the film. Just wait for the stop before you Twist and Shout!

Super Bowl Shuffle: Almost 20 years before that spaceship landed on top of Soldier Field, the Bears brought a different large silver object there: the Super Bowl trophy. Relive the glory of Walter “Sweetness” Payton, William “The Refrigerator” Perry, the punky QB known as McMahon, and the rest of the 1985 Chicago Bears as you scope out the Field and the adjacent Museum Campus on your bike cruise.

Decade between the Daleys: The 80s featured Chicago’s first woman mayor and first African-American mayor, as well as possibly the most contentious city councils Chicago has known in modern times.

Grant Park: The 1980s saw Grant Park transform into the festival grounds we know it as in most summers, hosting the first incarnations of the Taste of Chicago, Blues Fest, and Jazz Fest that collectively opened the gates to everything from Celtic Fest to Lollapalooza.

Lakefront Trail: Slide on those Raybans and cruise along the Lakefront Trail between Lake Shore Drive and the yacht clubs that line the downtown lakeshore.

Navy Pier: If you’re from Chicago, you may want to bike past this place. But if you’re visiting, it’s worth taking a break at Navy Pier.