For a crazy, unforgettable night, everyone needs to take part in Chicago’s favorite pastime at least once – a party trolley. Chauffeured around the city in a rented trolley car, you can experience 3 hours of moving dance party sing-a-longs with 24 – 30 of your closest friends. A typical Chicago trolley itinerary involves pick-up at a house or location of your choice, a few stops along the way for bars or photo opportunities, and a drop-off at a final destination – usually a bar or a house.
While this trip might seem like a good chance to get in your Chicago sightseeing, the level of rowdiness of the crowd will make that determination. With all of your friends in tow, you can capture great photos outside the planetarium with the skyline in the background. Additionally, you can visit some of the bars outside your usual boundaries without having to worry about taking multiple cabs. Set up your favorite tunes, stock up on your favorite drinks, and gather your crew for a night around town.
Of course with all privilege comes responsibility – planning a trolley can be a logistical challenge. As with any event, not all parts will go as planned. Here are some tips for navigating what could be the night of your life.
Questions to ask the trolley company:
- Will your “advanced sound system” amplify my iPod/iPhone playlist?
- Can we bring our own beverages on board (the answer is usually yes – but no glass)
- Is the trolley heated/air conditioned, and can the windows be opened?
- Is gratuity included in the credit card charge, or will the driver expect cash at the end of the ride?
- Can I get a discounted fare if I “like” you on Facebook?
Questions to ask the bars you want to stop at:
- Can you accommodate 25 people sometime between 8 – 10 p.m. with no cover and a limited line?
And finally, questions to ask yourself:
- Am I willing to corral 24 – 30 of my friends and hunt them down for their share of the cost?
- Do I have the patience for last-minute cancellations and added guests?
- Do I want to buy all the beverages in advance, or ask guests to BYOB?
- Am I willing to make sure the trolley is spotless at the end to avoid a cleaning fee?
Other helpful tips:
- To collect funds in advance, use a service such as Crowdtilt, which allows credit card payments and will divide the total cost among the final number of guests that attend
- If you bring on beverages, don’t rely on Styrofoam coolers – they will break. Purchase some cheap plastic tubs at WalMart to house your drinks and ice
- Your playlist sets the mood – but bring good old mix-tape CDs as backup in case they can’t plug in your iPod/iPhone. My approach is to start off with mood-boosting Top 40s, continue with solid dance music, and transition into 80s ballads or 90s rap by the time you’re on your way to the third bar. Consider you’ll need about 2.5 hours of music ready if you’ll be spending one of the three hours on bar stops
- Bring on trash bags, paper towels, Solo cups, etc. – clean up everything along the way
- The homeless people outside are always looking for a free beer handout. Proceed with your own discretion
- Clear communication with the driver is key. Provide an itinerary with addresses in advance, and make sure he/she knows the timing of each bar stop. Tell your guests when to return to the trolley, so no one gets left behind!
Have fun!!!
{Image via Coleman Forredondo}