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I'd like to be able to ride with my son in our bike trailer, but Chicago drivers are nuts and I'm hesitant to take him out with me. Are there any routes that are better for riding with kids?

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If you're riding with a trailer, you should be safer if you put a flag on the trailer so it's more visible to cars. But in my opinion, it's probably best to stay on the trails. Chicagoland bike federation actually has a lot of info on riding with kids - they recommend (from the site):

Lakefront bike path (beware of wind resistance with trailers . . .)
Burnham greenway (bonus: great bird watching during spring and fall migrations)
Palos/Tinley area
North Branch trail
Salt Creek trail
I and M Canal trail
Old Plank Road trail

They also recommend avoiding Wells (b/c of El posts), Armitage and Halsted (both too narrow).

If you want to check out the CBF article, it's at this link:
Hi Leigh - as part of the Boulevard Lakefront Tour, there's a special ride just for families! There are more details in the events section:
Sheridan Rd. from Plaza Del Lago in Wilmette up through all of the North Shore worked well for me with a bike trailer. Traffic is light, there are very few stops, and the lanes are quite wide. Traffic picks up in the mid to late afternoon.

Bumping this since it's a 7 year old thread and I'm preparing to take Eliana out and about soon!

We took Miguel everywhere in the trailer. Since we (and you) already have decent knowledge of good routes in general, you have a solid base to work from. Riding-with-trailer skill is more important than route selection. Some trailer tips are here.

People might honk and yell at you for "endangering" your child, but if they are yelling, that means they see you. No one* wants to hit someone, esp someone carrying a child.

Start with low stake trips (ie, ones where you don't have to be somewhere at a certain time) and have someone ride behind you to give you feedback on your roadway positioning. You need to get used to having a slightly "wider load" ie less clearance.

You need to take corners a little more carefully 1) to make sure you are visible and have enough clearance and 2) so you don't hit a curb cut which can lead to the trailer tipping

Just pretend you are driving a flatbed truck and make lots of eye contact. :) Good luck!
*Well, almost no one and anyone that does transcends questions of biking set up. I posted this in another forum recently, but it is relevant.


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