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How late in the winter season is reasonable for riding?

I'm looking at a job out in Northbrook but am cringing at the idea of a suburban commute. The route from my place to the office is 20 miles of mostly trails, and there is a shower on site. I used to commute into the city through February but those were years that were not Snowpocalypse or Polar Vortex. How late in the season could I expect to bike commute to the 'burbs? Any tips for winter distance commuting?

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The trails will not be maintained for the winter.

Its dark up in the burbs and you'll have to invest in a good headlight. 

Don't think I would ride trails too deep into winter but it would probably depend on how much snow/ice is on the ground.

As already stated the paths, in particular NBT, are not maintained when/after snow fall, but there was plenty of time this past winter that the paths were totally rideable. I don't know where abouts in Northbrook, but I did similar from Deerfield to Lawndale. There is the nice metra stops and depending on your hours you might be able to bring your bike. Clark->Chicago ave (Evanston) to Sheridan to Tower to (Northbrooklandia) was what I basically did during bad trail days and for the most part, totally fine.

That all being said, high visibility and sight is key. Right now, I keep seeing suburb skunks (literal) out and about with the decreased hours of light. 43 is okay during the summer, but gets kinda crazy during early dark specially round willow construction.

Not saying don't drive, just saying possible. I did also have to invest in heated gloves. : ( but that is way cheaper than a car.

ENvane and MK gave you good advice. Trails are bad during the winter and stay wet longer than roads. Not all of them get plowed. There are plenty of decent  roads you can take and based on the trails you like to use I suspect there is a pleasant  way for you to ride on many winter days. Where is your general destination and without publicly posting your home, what neighborhood are you departing from? 

A decent route that will get you almost to Northbrook on just roads:  Pick up Church St./Beckwith Rd in Evanston going west, north on Harlem, merge onto Lehigh going NNW into Glenview.  

From there, probably get onto Shermer Rd and take that into Northbrook, but I'm speculating.

Take whatever route you normally use to get to Evanston. Go west on Church to McDaniel which is the same as East Prairie. Take it both to Linden which is the border with wilmette. West to 17th. North a short bit to Wilmette Ave
West up a hill to Illinois. North curving westward on Illinois to Hibbard. North to Willow. West on Willow to Forestway. North [n Forestway to Tower. West on Tower crossing over Edens expressway to dead end. I think it'Skokie. North on that until your destination.

Two fat tire (4+ in) can get you to Nome from Anchorage.

http://www.adn.com/article/20140305/iditarod-invitational-cyclist-r...

https://www.youtube.com/watch?v=AJI6HKN3BTI
Note in the second half how far the tire sinks and the pedal strikes.

Three fat tires can get you to the South Pole.

http://www.icetrikes.co/community/ice-blog/south-pole-by-trike

http://www.gizmag.com/south-pole-fat-trike/30245/

If you do decide to ride the NBT. Please do NOT ride or walk on the XC ski tracks.

Amy - own a shop in Logan Square and used to commute to my house in Arlington Heights year round. Short answer is I was fine into the mid-20's and below that I would use the Blue Line to shorten 21 miles to 10 each way. Clothing was always base layer, wool or something similar outer layer and hooded windproof jacket (super light, super warm). Then great socks, shoes, gloves and hat and never got over 16 MPH average cause the last thing you want to do is sweat. Also, watch the leaves on the North Branch Trail and wooden bridges. When they are wet they'll put you on the pavement in a blink of the eye. Blue Line is worthless to Northbrook but some of the East Routes that take you to Skokie could be real valuable if you're running low on time, energy or warmth. Peace.

The trails arent maintained like the city but I've ridden the one in Lake Forest parallel to route 176 and it's mostly packed snow. That was years ago when I had a mountain bike and not in the past couple years where there's been 18" but try it, at least you'll have a story.

I rode a few times last year on some of the more mild days, this year I'll either ride or bus it to work, but after last year I picked up some studded tires since the NBT by me isn't cleared, but I can use it instead of taking Milwaukee.

I wiped out a few times because I was moving too fast, so I learned my lesson.  Avoid iced out ruts, run my tire pressure slightly lower, take my time, and dress with a water proof/resistant outer layer.  It was the falls that got me the coldest after getting wet.

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