Raggedy Inn
The man behind the desk was friendly and helpful, but check-in was the only high point. I walked into the dingy, overheated room and turned down the thermostat. The heat just kept blasting, so I finally turned it off. I took one look at the couch and resolved not to go anywhere near it during my stay. I checked for bedbugs--no danger signs. The bathroom seemed relatively clean, and the plumbing worked. The Internet connection was easy to access but extremely slow.
I have to admit the room was worse than expected, though expectations were low. I had booked it with 16,000 free Wyndham Reward points, so I didn't feel too bad about not complaining. Or leaving. Switching hotels wasn't in the budget this time. It would only be one night, and I planned to spend as little time in the room as possible. 
The River North location is convenient to nightlife and shopping and great architecture. Walk nine blocks to Water Tower Place and the John Hancock Observatory. Walk six blocks to Frontera Grill at Clark and Illinois for the best Mexican food you've ever had. Walk three blocks to Ed Debevic's diner ("Get in here!"). I even ended up walking 1.4 miles to Navy Pier, which is worth a visit if you have any interest in Shakespeare, stained glass windows, lake cruises, people watching, or any of a big variety of tourist activities.)