Wicker Park and Damen on a Chicago Layover

Chicago’s Wicker Park is built around the crossing where Milwaukee Avenue cuts diagonally across Damen Avenue and North Avenue, a minute from the Damen elevated train platform, and within a few blocks of that corner are three floors of secondhand books, the artist studios inside the 1913 Flat Iron building, an old freight viaduct rebuilt as a trail twenty feet above the street, and a rooftop bar on top of a 1929 Art Deco tower.

Record shops and a three-floor bookstore on Milwaukee Avenue

Milwaukee Avenue runs northwest out of the Loop and reaches Damen and North avenues at a slant, and the blocks either side of that corner are the commercial spine of the neighborhood. Myopic Books at 1564 North Milwaukee is the one to give real time to: three floors, better than 70,000 secondhand volumes, open noon to 8pm every day of the week, with the basement and the top floor reachable only by stairs and staff who will fetch things down if that is a problem. Reckless Records sits a few blocks southeast at 1379 North Milwaukee, open 10am to 7pm daily, and the vintage clothing shops fill in most of the gaps between the two.

If you would rather eat your way along the street than shop it, someone has already worked out the route: a two-hour walk on Saturday and Sunday mornings stops at four Wicker Park donut counters, leaving at 9am from a coffee bar on Division Street, and a place on it has to be reserved rather than turned up for.

Damen has no elevator, and the station house on Damen Avenue is the only way in, so a suitcase goes up the stairs to the platform and back down again in the middle of the journey rather than at either end of it.

The Flat Iron Arts Building at the six-corner crossing

Holabird and Roche put up the cream terracotta block at 1579 North Milwaukee in 1913, on the wedge of land the diagonal street leaves behind, as an ordinary office building with shops underneath. Artists began taking the upper floors in the late 1960s and never left: painters, printmakers, tattooists, costume designers, film editors and musicians work behind the doors along its upper-floor corridors now.

On the first Friday of every month, from 6pm to 10pm, those doors stand open and anyone can walk the corridors and go into the studios, with $5 suggested at the entrance. On the other twenty-nine days it is a working building rather than a gallery, so the visit is the facade, the ground-floor shops and whichever studio happens to have its door open.

The 606, a freight viaduct rebuilt as a trail

Eight minutes north of Damen station up Damen Avenue, a ramp at Churchill Field Park, 1825 North Damen, climbs to a path that runs 2.7 miles above the streets, from Ashland Avenue west to Ridgeway Avenue. The Bloomingdale Line was lifted onto this embankment in the 1910s and carried freight until 2001, after which the deck sat abandoned and self-seeded until the city, the Park District and the Trust for Public Land reopened it as a park on 6 June 2015. The name is the first three digits of every Chicago zip code.

It is twenty feet up, which is high enough to put you level with second-floor windows and above the traffic, and the planting either side of the path is dense enough that long stretches feel nothing like an expressway median. Twelve access points spaced about a quarter-mile apart carry seventeen ramps between them, all step-free. It costs nothing and runs 6am to 11pm.

Wicker Park, the park the neighborhood is named after

Charles and Joel Wicker were subdividing land out here in 1870 and handed four acres of it to the city as a park, which is where the neighborhood’s name comes from rather than the other way round. It sits three minutes south of Damen station between Damen Avenue, Schiller Street and Wicker Park Avenue: lawn, mature trees, a fieldhouse and a dog run.

The fountain at the center is not the original. An ornamental one went in during the 1890s, was pulled out in 1908 and replaced with a wading pool, and what stands there now is a reproduction of the first one, put back in 2001 along with copies of the benches and planted urns that went with it.

A rooftop bar at the top of Wicker Park’s Art Deco tower

Perkins, Chatten and Hammond finished the Northwest Tower in 1929 at 2018 West North Avenue, on the triangle of land facing the Flat Iron across the crossing, and gave a narrow limestone block a stepped crown and a pointed spire. From certain angles the spire and flagpole look like an animal with its head thrown back, which is how the building picked up the name Coyote Building from the gallery that opened inside it in the 1980s, and how the Around the Coyote arts festival got its name in turn.

A renovation between 2015 and 2017 turned it into a hotel, and the useful part of that for anyone with a few hours is the bar at the top, which takes walk-ins from 5pm, until midnight most nights and 1am on Friday and Saturday. It looks straight back down the diagonal of Milwaukee Avenue with the Loop towers stacked up on the horizon behind it. There is no ticket and no scanner, just a drinks list.

If you have five hours here rather than three, the sensible thing is to get back on the train and finish the ride in: the free circuit from Millennium Park down to the Chicago Riverwalk starts under ten minutes east of here, and the Great Hall at Union Station and the Fulton Market warehouses are a few stops beyond that.

Wooden platforms and cast-iron railings at Damen station

Damen opened on 6 May 1895 under the name Robey, after the street below, and took its present name in 1927 when Robey Street was renamed for Father Arnold Damen. Two timber side platforms sit at track level with cast-iron railings in a diamond pattern and hipped tin canopies over the waiting areas, and a $13.6 million rebuild that reopened on 22 December 2014 replaced the roofs, relaid the decking and put back reproductions of the original gooseneck lamps.

What the rebuild did not add was an elevator, on the fourth-busiest station of the Blue Line’s O’Hare branch. From here the airport is about 31 minutes and Clark/Lake in the middle of the Loop is under ten the other way, both direct, both on trains that run around the clock. The fare boarding at Damen is the ordinary rail one, since the $5 surcharge only ever applies to trips that begin at O’Hare.

Wicker Park is the argument for getting off the train early rather than riding it to the end. Six blocks cover everything on this page, the only queue in it is the counter at the bookshop, and the last stretch of the ride back out is one you were going to make anyway.