Cass,
I decided to take a bike ride and take a few phone pictures for this entry. It’s not a complete view of the city by any means, but a quick tour of basically a big circle around Chicago.
Chicago, Illinois

This is a Brown Line CTA train heading downtown behind my apartment. I currently live on the north side of the city.

Name: Gabe Holcombe
Age: 26
Occupation: I work for a large natural foods market
Current Location: Chicago, Illinois

I went further north from my apartment and took this picture at Wilson and Broadway in the Uptown neighborhood. Those are the Red Line CTA tracks and the Wilson station on the left. Basically, this area is amazing and weird and there will always be some sort of scene taking place in or around the station.
Hometown: Rochester, NY/Manhattan, KS

I love hand-painted signs and Chicago has a ton. These are some beautiful examples from the Uptown area.
Transportation: 85% bikes, 10% CTA, 5% bumming rides from friends

I biked south down the lakefront path towards the city. This is Belmont harbor. During the nicer days in spring and summer, there is a glut of tourists, slow walkers, rollerbladers, dentists on $5,000 carbon road bikes and other hazards which prevent a normal city cyclist from really having much fun. However, once you get south of the city, the path is quiet, beautiful and extends for a nice section of the lake in and into the South Shore area.
Best Food Spot: I like to go to produce markets and prepare meals at home in order to save money. There are tons of them around the city with varying degrees of quality and selection. Some of my favorites include Cermak Produce (I like the Kedzie and Berteau location and the North and Washtenaw store), Pete’s Fresh Market (Cermak and Rockwell), Edgewater Produce (Clark and Catalpa) and some other markets that specialize in specific ethnic cuisines like Joong Boo Market (Korean, Kimball and the Kennedy Expressway) or Patel Brothers (Indian, Devon and Rockwell).

I took a detour around the city and biked through the Pilsen neighborhood, which is just south and west of downtown.

Pilsen has tons of more detailed murals, but I like this one in particular.
Best Drink Spot: I avoid bars a lot, but there are a few that I like around town. Club Foot in the Ukrainian Village, Alice’s at Belmont and Central Park has the best karaoke in town. The Two-Way on Milwaukee in Logan Square for cheap drinks. Lots of good neighborhood bars and hole in the wall spots that I either can’t name or don’t feel like naming.

This is the Damen Avenue overpass over I-290. The CTA Blue Line cuts through the middle. Damen avenue is a nice artery with a bike lane that cuts through a good chunk of the city. The Sears/Willis Tower is in all of these pictures as a good reference point.
Chill Spot: There are lots of good spots to hang out or relax in the city that don’t involve a crowded beach or park. I have a short list of courtyards, empty beaches, rooftops, forgotten parks and other nice places to hang out.

I headed northwest into Humboldt Park, a huge park located in the neighborhood of the same name. It’s gigantic. There’s the Sears Tower again.
Shopping Gems: There are many great thrift stores in Chicago. Village Discount Outlet is a large chain in the area, and some are better than others. The ones in the farthest north and northwest regions seem to be less picked over than those closer to the more gentrified north side and Wicker Park. The Salvation Army on Devon and Hoyne is huge and has good stuff, too. For music stuff I like Midwest Buy and Sell out in Portage Park (Irving Park and Austin). For bike stuff, I like Smart Bike Parts in Logan Square (Armitage and Humboldt) and Roscoe Village Bikes (Roscoe and Seeley) in Roscoe Village, which is closer to where I live.
Favorite Thing About the City: That I can live affordably in a city that has a lot to offer. Shit, I don’t know. It’s Chicago, it’s a great place. It’s comfortable and stifling, beautiful and sometimes scary, all at the same time. Hard to describe. Come visit!

-Gabe