Jessica, N Milwaukee Ave over‎ I-90/I-94, Chicago, IL

Jessica rides a yellow Schwinn cruiser from A Nearly New Shop in Uptown

Where are you going? On my way home to wear out the new roll of drawing paper I bought. I'm experimenting with wallpaper designs. So far, it's not looking too hot. 

What are you wearing?  Levis high-waisted jeans, Zodiac USA boots a la Buffalo Exchange in Wicker Park, my brother's jogging beanie, a Sundance bag my mom bought way back when and a vintage Giants sweatshirt that my dad says my mom stole from him when they were first dating. 

Tell me about your bike, and where you got it? It's a yellow Schwinn cruiser I bought at A Nearly New Shop in Uptown, or somewhere just as far. Not sure of the year but I'm pretty sure there're a few different parts...

Why ride? To get lost. I love adventures. And parking downtown is expensive. 

Favorite ride? Along the lake from Oak to Montrose at night. No one's out, it's a little scary, but everything is so peaceful. 

While riding you …? Hand jive when I get the chance. 

How can Chicago improve bike infrastructure or be more bike friendly? I'd say more bike lanes on streets like Kedzie and Ashland. Ashland especially, it's super busy, but it gets you to a lot of neat places. Also - more bike stands! I hate locking up on a bus stop.

And other cool, funny tips or stories? 

The folks at the Kinzie Chop House are super wonderful. I was on my bike just across the street waiting for the light and I guess I didn't hold my balance too well because I totally ate it and my bike fell beneath me. Then some chick told me I was bleeding inside my foot. I looked down and was like "Oh man, I am bleeding, huh.." and went flush upon closer examination. (I'm stupidly squeamish). 

So I went into the Kinzie Chop House and was all like, "Uh, I know this is unorthodox, but I'm bleeding, I was wondering if I could use your bathroom.." and nodded at my foot. The lady at the host stand took one look at it. Her eyes widened and she offered to get me a napkin. She came back a minute later, "I wet it too.." I thanked her and proceeded to fiddled with my shoe. She did that awkward shrug thing and set her hands together as if to clap, "Um, would you mind doing that outside?" I guess I was pushing my luck. But hey, she was a total doll for getting me a damp cloth! I mean, it's better than a toilet paper tourniquet...

Gianna, W North Ave & N Honore St, Chicago, IL

Gianna rides a pink Raleigh Capri 410 step-through.

Where are you going? I'm on my way to work at Buffalo Exchange!

Tell me more about your bike and where you got it? I got my bike from Nearly New on N. Broadway. They're super nice and helpful there. It's a pink Raleigh Capri 410. 

What are you wearing? A large, over-sized, retro blouse from Buffalo Exchange. 

Why ride? To save money! Buying passes for transit can get really expensive. Also, its just the most fun way to get from place to place. I find it exhilarating. 

Favorite ride? Right now I would probably say taking Milwaukee to downtown...especially at night! There's nothing better then the epic feeling of entering the magical metropolis that is Chicago. 

While riding you? Talk to myself/sing. 

How can Chicago improve bike infrastructure or make Chicago more bike friendly? More bike lanes on all the major streets so that its easier to get around without feeling like your in the way of cars or having to go out of your way for a bike friendly route.