Chicago Trip Help

So in a week today on the 22nd of June I'll be going to Chicago for two days with my sister and friends. I'm the only one riding and boy do I plan on riding. The moment I get off the train I'll be riding to the hotel, to the destinations, and more. I have a couple questions for you guys though. First off, what should I do and should I not do when riding in Chicago? Secondly, what are some places I should visit or street's I should ride? I'm riding a fixed gear with a front break. I want to hear the thoughts on the first one from both safe and more dangerous riders. To hear both sides. All help would be super helpful.

Here's a picture of the bike by the way. This was when I finished the work on the frame and wheels. It's a little worn now though.

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Permalink Reply by Ken Gray on June 14, 2015 at 2:34am

I can't give much advice on where you should ride. A lot depends on where you are staying and what kinds of things you would like to see. (We have tons of interesting things to do and see here). But I would suggest you buy the best lock that you can and be very careful to avoid locking your bike to "sucker poles" and the like. We don't want you to remember Chicago as the place where your bike got stolen.

Permalink Reply by Joshua Lowery on June 14, 2015 at 2:47am

Well I'm staying at the Courtyard by Marriott Chicago Downtown River North and I have a U Lock and a wire lock for the front wheel. The hotel I'm staying at has vallet parking for bikes.

Permalink Reply by Gene Tenner on June 14, 2015 at 4:57am

My favorite is the lakefront trail. North and south are beautiful. Ditto on the good locks.

Permalink Reply by This PBL dosnt make me feel safe on June 14, 2015 at 5:41am

Don't ride on Lake Shore Drive.  In general, any roads in Chicago that are two lane in each direction are not good to ride on.  Since you're here on the weekend, the Lake Front Path will be mobbed, but its still worth riding.  If your doing the usual touristy things, you'll mostly be in the Loop/Near North area which is not the greatest area to ride.  If you want the ¡AUTHENTICO! Chicago biking experience, in the evening take a ride up Milwaukee Ave from the downtown to six corners (Milwaukee/Damen/North).

Permalink Reply by Joshua Lowery on June 14, 2015 at 5:54am

The 22nd is a weekday but I'll keep all that in mind.

Permalink Reply by Jim Reho on June 14, 2015 at 7:40am

Although I'm not fond of fixies, it's apparent that you put a lot of work into making your bike really beautiful and unique.  So, like everyone else says, PLEASE keep it safe wherever you go.  Otherwise, have a great stay and cruise along the lake shore if it isn't too crowded. 

Permalink Reply by Fran Kondorf on June 14, 2015 at 10:48am

Don't; Ride on sidewalks or Lake Shore Dr., pass on the right

 Do;  Headlight at night (it's the law)

        Call "on your left" when passing

        Lakefront trail on a weekday

        Attempt to stop at red lights and stop signs

        Enjoy your visit!

Permalink Reply by daWillinChi on June 16, 2015 at 3:16am

Put your foot down like a stop when you see cops around.

Attempt to stop at red lights and stop signs

Permalink Reply by grayn8 on June 14, 2015 at 3:53pm
Chicago is a big flat grid, so recognize the hundreds / Cartesian plot of Chicago and you'll basically always know where you are. That being said there are the diagonals and off grid and these are usually lots of fun to ride: Blue Island, Archer, Milwaukee, Elston, Clark - all super nice. (Ogden can be a beast, but is damn useful). Get a free bike map at a LBS. explore neighborhoods. And if your riding hard and fast, carry a tubes/co2 whatever. Lots of broken glass.
Permalink Reply by Filka Bean on June 14, 2015 at 6:21pm

I see "neighborhoods" here- one my favorites as a local is to google a new place to eat that's far off my usual beaten track, and then chart a route using the bike routes map (which is also online as a pdf), cause food is another great thing about Chicago... 

And I second the "4 lane streets are a drag" sentiment too, although some of the larger one-ways are actually pretty great.  The cool thing about Chicago's square-grid plan (besides the super-easy navigation with numbers) is that if a road looks or becomes sketchy you can just jog off a block or two until you see something that seems better.  And it works even better if you don't really care where you end up or how long the trip takes!

Permalink Reply by Joshua Lowery on June 15, 2015 at 5:37am

Does that app tell me the turns I need to make even if I'm playing music?

Permalink Reply by Joshua Lowery on June 15, 2015 at 6:38am

I use a blue tooth speaker.

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