I'll be traveling to Chicago for the weekend and would like to take a casual ride through the city. A friend of mine will also be joining who isn't comfortable riding on busy city streets. Are there any bike friendly trails or paths in or around downtown? A 5-15 mile route would be ideal. Any recommendations on where to rent a hybrid/cruiser bicycle would be awesome too.
The fantastic Lakefront Trail would be a great choice, a paved path that extends for 18 miles along the shoreline of Lake Michigan. It runs from Ardmore on the North Side to 71st on the South Side. It's a very lively path (pedestrians have the right of way) and a great way to 'see' the city.
Run, walk, bike or rollerblade with the blue waters of Lake Michigan to one side and gorgeous, green parks to the other. There's so much to soak in in addition to the skylines views — pass by peaceful boat harbors, serene nature sanctuaries, bustling boardwalks and more. Along the trail are parks, beaches and gardens; recreation areas including playgrounds, soccer fields, volleyball nets and tennis courts; and amenities like washrooms, drinking fountains and concession stands.
As for bike rentals, there are lots of options, such as Bike and Roll Chicago , Lakeshore Bike, Divvy, Wheel Fun, Bobby's Bike Hike, just to name a few. You'll have to check to see which one(s) might have the hybrid/cruiser bicycle you'd like.
Happy trails to you!