Emily, S State St & W Jackson Blvd, Chicago, IL

Emily rides a Raleigh Carlton road bike from a Nearly New Bike Shop 

What are you wearing?  My roomie's black princess-sleeve shirt and thrifted Bloomingdales wool pants.
Where are you going? Visiting my friend at Merz's Apothecary after an interview at the Peggy Notebaert Nature Museum (I got the job! It must have been my fancy pants...)
Tell me about your bike and where you got it: I ride a Restored Raleigh Carlton from Nearly New Bike Shop
Why ride? Good for da soul, body and da earth. 
Favorite ride? Day trip to Three Floyds in Munster, IN.
While riding you …? Sing and whistle. 
How can Chicago improve bike infrastructure or make Chicago more bike friendly? Death to the car!!!! Or more realistic alternatives include: fill in potholes, offer bike fix-it stands, enlarge existing bike lanes and add more bike paths (hellooooo, Bloomingdale Trail!). Also, educate drivers about bike safety! I think all Chicago drivers should be required to pass a bike safety test before hittin' the road.
And other tips? A tip for all you ladyz and fellas out there: helmets are sexxxxy! Honestly, you look like a damn fool if your don't wear one. Protect your noggin!

Lauren, S State St & W Jackson Blvd, Chicago, IL

Its been pretty rainy here in Chicago but there are still tons of dedicated cyclists riding through it, like Lauren who I caught yesterday afternoon right before a downpour.  

Lauren rides a grey cruiser purchased from Uptown Bikes

Where are you going? I am on my way to a dentist appointment on my lunch break. 
What are you wearing?   I am wearing a navy dress, violet military jacket, running shorts, and blindingly colorful running sneakers. 
Tell me more about your bike, and where you got it? I'm actually not quite sure what type of bike it is. It's grey; a cruiser.  I got it from Uptown Bikes, but by this point almost all of it has been replaced by parts via Johnny Sprockets.
Why ride?  I initially started biking because it was a time saver - I was able to be more efficient with my time since since I was no longer waiting for buses or trains or I could just bike to the train station thus saving me about 10-15 minutes. Now I ride because it saves so much money, I  have freedom to come and go as I please, it's a great way to be active, and of course, it's still much more efficient than any other mode of transportation especially if transfers are necessary. Rain, shine, or blizzard, I am biking year round. I guess I'm addicted.
Favorite ride? I love biking along the lake during my work commute or on the quiet side streets in neighborhoods.
While riding you …? Now that I am no longer focused on trying to avoid pot holes, aggressive cabbies, or ignorant door openers, I love to take in the smells (the fresh air along the lake or fresh earthy and flower smell after a good rain) and sights (the lake, the skyline, interesting houses, interesting people, nature) as well as focus on my day (mentally balancing finances, planning dinner, and reviewing my calendar). I also love taking random streets to discover new areas of the city.

How can Chicago improve bike infrastructure or make Chicago more bike friendly? Oh my gosh, where should I start? The pot holes/crazy uneven dips on the roads have definitely broken my bike more than a few times despite my cautious eye. Bike lanes are also a must (have you ever biked down North Ave? I'm lucky I've survived!). And almost tied for first would be educating people (drivers and pedestrians alike) about cyclists (e.g. how close is too close, awareness, importance of using a blinker when turning). It would be also fabulous if companies offered incentives for biking to work - it would be great to see more people biking as well as receive some benefit for choosing 

And other cool, funny tips or stories? Hrmmm... I don't really have anything really interesting to share. The only thing I guess I could mention is that I love the Naked Bike Ride. It was actually my interest in participating in the event that made me find a bike and my passion for biking despite not touching one for over 15 years. I would definitely participate in the Naked Bike Ride this June - I plan on being there and coming prepared with bags of body paint!