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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.

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    Dorothy's suggestion of the Lakefront Trail is perfect, especially that it's less crowded at this time of year. To add to that, depending on where you're staying, check out the 606. Many streets in Chicago have excellent bike lanes. Google Maps' bike layer is up-to-date and accurate. Also, this seems to be out of your distance range but do consider the Chicago Perimeter Ride which is this weekend! facebook.com/events/958416154285424 I'm flying back to the city for it. It's a chill informal ride, traffic is sparse for most of it. Lots of fun. ~100 miles if you go all the way. – Brad Sep 28 '16 at 19:54
  • Also, the Perimeter Ride goes down the Lakefront Trail on Saturday Morning, so if you want to kick off the ride with us, you're welcome to do so. Starts at the Buckingham Fountain in Grant Park, around 8:30 AM. (Honestly, probably end up leaving around 9:00 AM.) – Brad Sep 28 '16 at 19:56
  • Here's some more rides over the weekend: thechainlink.org/events – Brad Sep 28 '16 at 19:57
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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!

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I'll add that many streets in downtown Chicago have a bike lane, and for the most part your car driving neighbors are used to and wary of bikes. There have been some recent incidents in the news, but the sheer volume of bikers in Chicago proves it's quite safe. Happy cycling.

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