First, the most basic tip would be to dry your dog's paws with a towel after a reasonably brief walk. Removing salt and chemical pellets quickly will prevent chapped, cracked and painful paws and it will prevent your dog from ingesting salt and/or chemicals, which, needless to say...is bad. So a quick paw wipe down with a towel is the first place to start.
If your dog will tolerate boots, I say go for it! They do work and after you use them a few times, they are not that hard to put on. Most dogs get use to them quickly. Avoid adjusting them too tightly, which can lead to reduced circulation. For me, the rubber balloon boots work well (www.pawzdogboots.com), but can sometimes be a bit tight around a dog's ankles. You will probably have to do a bit of trial and error to learn the best fit for your dog and how to put them on quickly. I would suggest stretching them out to break them in before their first use. Ruffwear and Muttluks are more sophisticated brands that are popular in the city. They perform reasonably well, but I have noticed they do have a tendency to fall off if not adjusted snugly. Some folks have saved money and made homemade boots using balloons and baby socks, but I have no experience with that method.
When it comes to de-icing and snow melt products there are no perfect solutions. Obviously rock salt and chemical pellets can do harm to your pet, both internally and externally. Sand might be the least intrusive method, but it only provides traction and does nothing to melt the ice. If you want to make that ice disappear and be conscious of your pet's safety and health, there are two popular choices. The first is Safe Paws. It is salt-free and environmentally friendly and is green/blue so it is visible. It does claim to be the #1 selling brand, but I've read mixed reviews of its effectiveness and some have said it is harmful to concrete. The other popular choice is Morton's Safe-T-Pet. This product is salt and chloride free, but does contain urea which is high in nitrogen (as in 46% nitrogen) so if used routinely and in high doses it can be harmful to greenery. Its performance in low temperatures is questionable as well.
Be aware, especially during the holidays that mistletoe, holly and lilies are poisonous to dogs. Macadamia nuts and yes, chocolate, are also toxic to dogs. If your dog does ingest a toxic material you can call the ASPCA Animal Poison Control Center in Urbana at 888-426-4435 24 hours a day.
Lastly, a little Musher's Secret or petroleum jelly on the paws, between the toes, can be a sturdy and preventative barrier to protect against winter elements if your pup does go out in bare paws.
Winter is coming, but with a little proactive prevention your dog can brave the Chicago sidewalks safely! Now if we could figure a way to keep all the snow looking clean...