I got a new job (thank you) and it's on LaSalle Street. I'm coming from the Wrigley Field area. I've been a bicycle commuter in Chicago for near 20 years and have had to occasionally ride through or near the Loop but, dang, give me your pro tips on riding in The Loop every day. For the past several years the most aggressive traffic I've been in is Halsted at Milwaukee.
LaSalle St is a tough route given the number of accordion buses. The Dearborn St bike lane from Kinzie south would be a better option once you hit the Loop. Wells St has a bike lane, but once it hits Wacker it's a shared lane, and fairly chaotic. I assume you're close to the Lakefront Trail? Taking the lakefront to Randolph or Monroe before heading west would work.
I ride from Clark/Diversey every day. I would consider myself a very confident rider.
In: Clark all the way. Pretty relaxed ride in my opinion but there are tricky spots around Francis Parker (during the school year), between Armitage/LaSalle (too wide, sometimes fast), and between Chicago/the River (wide, congested, no bike lane, but very well-timed lights). Wells could be a good route if you care about a painted lane, but can actually be congested for cyclists, especially south of Chicago.
Out: Dearborn all the way to the park, Stockton through the park to Wrightwood, then north on Clark.
LFT is the safest/most car-free but is a bit longer.
Use Divvy. The bike valet stations take bike parking out of the equation, and also allows one-way bike commuting if there's weather or you have other plans, etc. It's also nice to never have to clean a messy bike in the winter. I don't even own a bike with fenders anymore.
Get a bell and lights. Pedestrians will stand in bike lanes at pretty much every loop intersection, so bring some patience too. It's worse for contraflow lanes like Dearborn.
As for routes? I've never had a problem riding Wells in and Dearborn out. They both can get really busy with other cyclists sometimes, but everyone generally behaves. I sometimes take the lakefront trail, but it can get super busy with beachgoers/tourists during summer afternoons. The high water is making the stretch between NP Flyover and Oak Street particularly nuts right now.
From roughly Wrigley would be down Clark to Halsted, Halsted to Clybourne, then Division to Wells which gets you into the loop. It's all marked though city street riding is its own special brand of hell different from the lake front. Don't shoal, don't run lights and keep your eyes open. You'll learn the lights and traffic patterns after a while and can expand your style from there.
There are lots of routes and there are already good suggestions here. my biggest suggestion is finding the place you want to lock your bike, making sure you have used two locks or a cable and a lock so both wheels and the frame are attached to something that is more or less immovable. Strip all the stuff that is easily grabbed such as a computer, lights, pump etc and stick them in your bag before you leave the bike and go up the elevator. If you have a Brooks saddle or just want it dry, it is nice to have a seat condom even if it is simply a plastic bag.
^ And read the Chainlink discussion about locking to U-locks and pick a side! ^
Curious here, how is it working out dav?
Not bad. Quite enjoyable honestly. I do Sheffield, Clybourn, Wells to get to work. I have access to an indoor bike room so I'm good on security. I've always been a person who stops at lights so that wasn't an adjustment. Things I've had to get used to quick: Sometimes I have to take the lane on Wells in the loop for a block or two. The cars are tolerant and don't become over aggressive so that's fine. The afterwork rush is pretty aggresive as far as my fellow cyclists go. When I come to a stop there are suddenly five other cyclists on my left, right, and going around me because half of them want to wait for the green light two bike lengths into the intersection and a few of them are just waiting to go through the red.
Interesting dav. It's great you have a bike room! I had set one up with showers, changing area, lockers, and a badge-in only room for bike storage with a security camera in the storage room. Air hose and tools too with big "bathroom key" handles so people couldn't walk off with them accidentally in their pocket.
It is all fascinating from a manners and safety standpoint for sure. The two bike lengths at a stop light rarely gets someone home more quickly unless it helps them beat the next light by two bike lengths, which is not enough from a risk/benefit standpoint.
Fixing the intersection shoaling problem would be such a win for cross street pedestrians, and would convey to motorists that cyclists are well-mannered and have high regard for their fellow travelers versus conveying a free-for-all (we can call it anarchy) culture that doesn't benefit cycling when cyclists set forth this standard for motorists, by conveying "go ahead, be aggressive, quite frankly I am!"
Not sure if you ride with one, but blinky light in the day time where there is bright light as well as long shadows in the loop seems to add some visibility. It will start to get dark earlier, although we don't set the clocks back until Nov. 3 I believe.