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...

Erica, Lakefront trail at Division, Chicago, IL

Erica rides a Peugeot Carbolite 103 from A Nearly New Shop

Where are you going? I'm about to sit down with a book to read by the lake and enjoy the nice weather.

What are you wearing? A shirt I got at Forever 21, black skinny jeans from Gap, and my bleach-stained purple Vans sneakers.
Make/model color of your bike, and where you got it? I have a blue Peugeot Carbolite 103 from A Nearly New Shop.
Why ride? I got tired of having to rely on public transportation all the time. After two semesters of taking the red line to school every day, I grew very impatient with its unreliability. It’s also my first summer living in Chicago and my school doesn’t distribute U-Passes to students taking classes over the summer. I realized biking would be a good solution to my frustrations towards taking public transportation and would also be a good way to get around without having to pay for the CTA.
Favorite ride? I’m very new to biking in the city, but so far I really love the lakefront trail, especially when it’s not very busy.
While riding you . . .? I’m very careful about watching for any cars, pedestrians, potholes, etc. I just started riding in the city about a week ago, so I’m still getting the hang of things, including the gearshift on my bike, which is very new to me as a person who’s used to riding mountain bikes.
How can Chicago improve bike infrastructure or make Chicago more bike friendly? More bike lanes and paths would be great. And it would also be nice if they’d fix the potholes, especially the ones on the bike trails. They should also try to better educate drivers and bikers about road safety.
Have any tips for new cyclists like yourself? Google maps can really help you plan a safe route when you’re getting around in the city, especially if you're new to it like I am

Ruby, 2500 Block of North Kedzie, Chicago, IL

Ruby rides a Schwinn World sport called Black Betty from A Nearly New Shop.

Where are you going? To Boulevard Bikes. My dear Betty is missing her chain!

Tell me about your bike, and where you got it? My bike, Black Betty, is a Schwinn World from the '80s or '90s I assume...adopted from Nearly New in Lakeview.

What are you wearing? I'm wearing a red hat with awesome ear-warming abilities, blue wrap skirt and boots that are all from thrift stores. My "stuffed animal" coat is from an estate sale in Seattle, and my gloves were my grandma's. 

Why ride? Chicago is wonderfully flat - why not?
Favorite ride? I don't know if I have a favorite, but I like biking down Webster Ave at night. No potholes, virtually no street lights or traffic - its perfect.
While riding you …? Worry about all the different ways I could be hit by a car.
How can Chicago improve bike infrastructure or make Chicago more bike friendly? Chicago streets need clearly defined bike lanes so bikers can feel safe and drivers can watch where they're going.
Any other tips? Don't bike in Wrigleyville after a Cubs game or some drunk guy will push you off your bike into a telephone poll for a laugh. And wear a helmet!!