If you are flying into Chicago’s O’Hare or Midway airports, these both have accessible stations for taking the “el” train into the city, which can be a good option for getting to your hotel, especially if you do not have a lot of luggage. All el trains are accessible, including having places for securing wheelchairs; and most, but not all, el stations are accessible; those that are accessible can be found on this list. Many stations rely on elevators, which can sometime be out of order, but updated information about elevator outages and other situations that may affect accessibility can be found here.
There are several other options for other accessible airport transit, including Curb, which provides wheelchair accessible taxis.
For getting around the city itself, it is best to avoid driving, as parking is expensive and is often located in underground garages, which have height limits and cannot accommodate tall vehicles, including some vans. The CTA city bus system is entirely accessible, and the Metra train and most of its stations are also accessible.