Lakefront Cruise in Chicago

Lakefront Cruise in Chicago

City Tour, 9 miles


This ride will take you through Chicago's North-side and place you right out on the shoreline of Lake Michigan. Heading South you will have views the city's looming skyline, rest in it's shadows at Oak Street Beach and cruise back North through Lincoln Park where there are plenty of worthy detours along the way. 

This is a route I take regularly in the summer with my son in tow. We get quality father-son time, with the wind in our hair, we see the city and draw inspiration and ideas.


Click map image to open printable PDF

Click map image to open printable PDF

Route Map



Divvy Bikes$7 daily


  • Bike Chicago - $36+ daily for cruiser, city, mountain, road, electric, bakfiets, tandem, kids, trail-a-bike, trailer or child seat
  • Bobby's Bike Hike - $32+ daily for cruiser, mountain, road, tandem, kids, junior, trail-a-bike, trailer and child seat includes helmet, maps and lock

Train Stations

Start and end of route - Wellington (Brown Line) or Belmont (Red Line)


What to Bring?

Bathing suit, towel, picnic lunch, sunscreen, money for food stands

Route Highlights:

A. Heritage Bicycles General Store  2959 North Lincoln Avenue || (773) 245-3005

Fuel up for the ride with coffee and a snack while the bike tires get pumped and we get geared up.

B. Peggy Notebaert Nature Center  2430 North Cannon Drive | | (773) 755-5100

Beautiful nature preserve in the heart of the city. Birds and wildlife can be viewed with a stunning skyline backdrop. This place looks impressive at anytime of day and the museum is a great place to stop with kids.

C. North Avenue Beach  1600 North Lake Shore Drive | | (312) 742-5121

The pointe at North Ave Beach is bustling with activity in the summer. Castaway's is a ferryliner turned bar, outfitted with bike rental stations and dozens of volleyball courts. Great views and people watching from here.

D. Oak Street Beach  1000 North Lake Shore Drive |

This is the destination beach for all of Chicago. Run in the sand and grab a snow-cone from a vendor and take a seat in the shadow of the John Hancock Center as you take in the views.

E. Lincoln Monument, Chicago History Museum  1601 North Clark Street | | (312) 642-4600

Right behind the Chicago History Museum stands a 15 foot tall Abraham Lincoln bronze statue. Placed in the center a lush garden, with plenty of benches and grass to stretch out in.