4400 S Racine Ave (1200W, 4400S)
Chicago, IL 60609
Chicago Trolley’s fleet of 50 custom-built trolleys are the best way around if you’re planning to hit several watering holes over the course of an evening. Plus, you can drink as they drive. Chicago Trolley charges a very reasonable rate and each trolley accommodates 32-36 people.
If you hire a trolley, pick a place that is central for your group and large enough to hold everyone. In summer, you’ll probably want to start at a place with a beer garden. You’ll also want to pick venues beforehand that are about 20 to 30 minutes apart in distance so that you can “enjoy the ride.” Chicago Trolley permits alcohol in cans and plastic on their trolleys (no bottles or kegs), so bring a couple of those cheap styrofoam coolers you can buy at Walgreens or CVS that can be discarded at the end of the night. Be sure to chat with the driver, not only for where you want to go and the best route there, but also because they often lead trolley tours around the city and can be a wealth of information for whatever you want to know. Cheers!