Hyde Park: A Presidential Tour

Cycle Chicago, Sightseeing Ride, Hyde Park: A Presidential Tour

This bike ride takes you past some of Hyde Park’s most notable landmarks, including President Barrack Obama’s home; the University of Chicago’s Law School, where he taught for several years; and the South Shore Cultural Center, where he and Michelle held their wedding reception. Although short, this ride will give you a feel for the culturally rich yet refreshingly diverse neighborhood that nurtured the Obamas. Keep one eye on the traffic and the other on the beautiful sights that are so plentiful in this, one of Chicago’s most storied and significant communities.


Mostly light traffic along the boulevards, which are designated as bike routes but do not have painted bike lanes. There are, however, a couple of congested spots along the way, and traffic on some of the boulevards can move quickly, so be alert.


CTA #6 Jackson Park Express bus stops at 58th Street and Stony Island Avenue, about four blocks north and east from the start of this ride at Midway Plaisance and Blackstone Avenue.

By car, exit Lake Shore Drive at 57th Street. Follow the exit as it curves west and then south around the Museum of Science and Industry. After about half a mile turn right onto Midway Plaisance at 6000 south on Chicago’s street grid. Drive west two blocks to the intersection with Blackstone Avenue and park. Parking is usually plentiful along Midway Plaisance.

Food and Drink

There is a large selection of restaurants in Hyde Park and plenty of drinking water along the lakefront.

Side Trips

Oriental Institute, Smart Museum of Art, DuSable Museum of African American History, Museum of Science and Industry, Frederick C. Robie House, etc.


More Details

From long before Barack Obama moved there, Hyde Park has been a dynamic, culturally endowed and racially integrated community. By some accounts, 1892 was the pivotal year. That’s when Hyde Park, conceived as an exclusive community, was annexed to Chicago; the World’s Columbian Exposition officially began; and the University of Chicago opened its doors. These three forces have played a huge role in defining the character and development of Hyde Park. Over the years, Hyde Park has built on this rich heritage, piling on major academic, scientific, literary, architectural and cultural accomplishments.

All these achievements make the area a great place for a bike ride, providing sights and stories, heritage and tradition. Thus, any ride through Hyde Park is more than a casual spin. You can’t just speed by murals and roundhouses, gargoyles and gardens – from community to Japanese to lakefront - without becoming curious. You can’t bike by places associated with a Rockefeller or a Wright, an Oppenheimer or an Obama, without wanting to learn more.

Thus, this ride is also a tour, albeit an introductory one. Space does not allow us to fill in the details behind the sites, but just seeing some of the more prominent, historical and presidential places in Hyde Park will surely jump start further exploration on your part. The area has an astonishing number of places to see – no, make that experience. You will find Hyde Park intriguing from bookstores to Promontory Point, which many Chicagoans regard as the best place to relax along the lakefront, from coffee shops to museums, from bike paths to the University of Chicago’s picturesque campus.


Ride Log

  • 0.0 Bike west on Midway Plaisance.
  • 0.3 Turn right on Woodlawn Ave. 0.5 Turn left on 57th St.
  • 0.6 Cross University Ave and enter the Quad. (Yes, bikes are allowed, despite the sign about pedestrians only.)
  • 0.7 Circle path, return east.
  • 0.8 Turn left on University Ave.
  • 0.9 Turn right on 57th St.
  • 1.0 Turn right on Woodlawn Ave.
  • 1.2 Cross 59th and turn right on the next street, Midway Plaisance.
  • 1.8 Cross Cottage Grove Ave.
  • 1.9 Bear right for Payne Dr.
  • 2.2 Cross 57th St and bear right on Payne Dr.
  • 2.4 Cross 55th St and bear left on Payne Dr.
  • 2.9 Cross Cottage Grove Ave and follow the street left as it crosses Drexel Blvd, with fountain on left.
  • 3.1 Turn right (east) on 51st St.
  • 3.5 Turn right on Woodlawn Ave.
  • 4.2 Turn left on 57th St.
  • 4.6 Ignore bike sign to turn for Promontory Point. Continue under bridge.
  • 4.8 Cross 57th St, then Stony Island Ave, picking up path (also a sidewalk) going east. Path curves along 57th St as it heads toward lake.
  • 5.1 Bear left under bridge.
  • 5.2 Bear left going uphill until reaching Lakefront Path that runs along Lake Shore Dr. Turn right (north) on path.
  • 5.3 Bear right onto Promontory Point.
  • 5.7 Bear left to take Lakefront Path south.
  • 7.3 Turn left on path along Marquette Dr.
  • 7.8 Turn right and bike along fence.
  • 8.2 Slow down and turn left into South Shore Country Club.
  • 8.4 Turn around and ride back.
  • 8.6 Slow down and turn right.
  • 9.6 Bear left and go up path that leads to Lakefront Path. Turn right (north).
  • 10.0 Immediately after crossing Hayes Dr and a small bridge, turn right to circle back under that bridge, heading west.
  • 10.2 Bear left on path along Hayes Dr.
  • 10.6 After passing The Republic statue, turn right on first path going north into park.
  • 10.7 Cross bridge onto Northerly Island. Bear left.
  • 11.1 Visit Osaka Japanese Garden on foot.
  • 11.2 Bear left three times to continue north then west.
  • 11.3 Cross Cornell Ave, then Stony Island Ave and pick up Midway Plaisance, riding west in the street.
  • 11.6 End ride.
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    18.121 km / 11.26 mi

    Total Distance

    76 m / 249 ft

    Total Ascent

    76 m / 250 ft

    Total Descent

    183 m / 599 ft

    Highest Point

    Ride type:
    Mountain biking
    Road riding
    Kid friendly
    Rail Trail
    Difficulty: Easy (Blue)
    Ride Duration: <1 hr
    Fitness Level: Low
    Shared Bike Path - Paved
    Shared Bike Path - Dirt
    On-Road Bike Lane
    Off-Road - Fire Trail
    Off-Road - Rail Trail
    Off-Road - Single Track
    Off-Road - Downhill
    Mobile Coverage: Excellent
    Estimated Distance: 18.0
    First Aid
    Bike hire
    Bike servicing
    Accessible by bike
    Accessible by car
    Accessible by public transport
    Accessible by shuttle / uber
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