Cool Chicago: The Bloomingdale Trail


COOL CHICAGO: The Bloomingdale Trail
Abandoned elevated train line turned gritty urban park
: Humboldt Park / Wicker Park / Bucktown
Address: 1600-3000 W. Bloomingdale
Cost: None
Best for: Urban explorers, active individuals, visitors who want to “live like the locals”

This week marks the debut of my new Cool Chicago series focusing on the awesomeness of the Windy City, which I haven’t written about nearly enough. Twice a month, I’ll be highlighting some of the coolest stuff in town, like offbeat restaurants, strange city parks, unusual museums, street art, or anything else worthy of attention.

The debut edition of Cool Chicago highlights the Bloomingdale Trail, an abandoned rail line on the city’s northwest side. Unlike the High Line in New York City, which has been completely restored and designed for public use, the Bloomingdale Trail has not seen a single dollar in renovation. In fact, it’s technically illegal to even go up there, but that law is not enforced, since the police have better things to do.

Signs tell visitors they’re not supposed to go up there. But people do all the time, to the point that there are 36 Yelp reviews of the trail, and I’ve never heard of anyone getting in trouble for going up there. (Disclaimer: The signs officially indicate: “Violators will be prosecuted.”)

On a nice day, you’ll see lots of runners and folks walking their dogs, trying their hardest to avoid the broken glass and random holes in the ground that you’d expect to find on untouched land.

The good news is that the city has finally realized how much potential the Bloomingdale Trail possesses, and they’re in the early stages of fixing up the old rail line into a proper walking and biking path.

danger sign

For now, to access the path, you’ll have to find one of the breaks in the fence. The easiest spot to get on to the Bloomingdale Trail is at N. Leavitt and N. Milwaukee Ave., across the street from the Aldi, just after you go under the tunnel.

Walk under this tunnel, then turn to the left and you’ll see the break in the fence that allows urban explorers to walk up and enter the trail.


Once you get up there, you’ll have easy access to views of the Chicago skyline, neighborhoods like Wicker Park and Humboldt Park, and some of the city’s most interesting street art.



The path, much like the city it resides in, is a little rough around the edges but has a lot of character and charm. It’s not paved, so watch your step. You may even see occasional evidence of a former or current homeless encampment.


The sights include up-close views of the blue line train, neighborhood apartments, and the streets of Humboldt Park.






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About Scott Shetler

Scott is a Seattle-based journalist and blogger who puts a quirky spin on travel adventures around the world. He has been featured in Travel + Leisure, Connect Magazine, Matador Travel, and the Washington Post.

6 comments on “Cool Chicago: The Bloomingdale Trail

    • The High Line is amazing… I can’t wait until this trail is properly developed. For now, it’s a great spot for solitude that you don’t often get in a metropolis.

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