Second City Trolley 312.532.8542 Or E-mail us

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I hired Second City Trolley for my birthday this past Saturday night. The trolley picked us up at 9 PM sharp and our driver, Ali, was the best. He helped us pick out places to stop, set up the music, and was an all around very nice guy. Myself and 31 of my friends all agreed that it was one of the best nights we had ever had in Chicago and we starting planning out the next time we would arrange for another trolley. We stopped at Wrigley Field, Buckingham Fountains, the Museum Campus, and the Bean. All stops were perfect and I highly recommend the same route! Thanks Second City Trolley!

I booked Second City for a bar hopping trolley for my best friend's bachelorette party. Her party was on Saturday night and we were really, really pleased with the service. They answered any questions I had prior to the event, called to confirm, our driver was on time and very pleasant, and the entire trolley ride went without a single hitch. Thanks Second City! I will always recommend you!

A thousand thanks to Second City Trolley /Limo. What a great service. We had a few hours to fill between the wedding and the reception. The driver got us out to the lake for pictures and then got us to our destination on time on one of the worst traffic days in the City of Chicago. I would highly recommend Second City Trolley. The Sister says" Thanks Doug and Tom".

A couple friends rented a barhopping trolley on 9/29/12 for their birthdays. I was just a guest, but I had a great time. I'll echo other remarks that the trolley was among the better maintained that I've been on: clean, reasonably quiet, comfortable ride, good sound system. Our driver was a younger guy and dressed casually (which is good when you're partying with a bunch of 20-somethings; you don't necessarily want a 50 year-old in a tux). He was very professional and put up with our lack of planning like a champ. (If you're planning a barhopping trip, I suggest you research your route in advance. Some bars are not too keen on you showing up with 30 people that are already quite tipsy. We take up a lot of space and do most of our drinking en route.) I also have to show special appreciation for these guys helping me find my lost phone. I had left it on the trolley on Saturday night and called the company at 3am. Surprisingly, someone picked up at that time and found my phone on the trolley. A really nice effort that late in the night (and also a nice display of human decency to not claim ignorance and sell it on Craigslist). If I book a trolley of my own for another event, Second City will be at the top of my list.

This review was written by my wife, but you get the idea: My experience with SECOND CITY TROLLEY & Rolls Royce RENTALS was incredible. Bottom line - costumer service. A group of girlfriends decided to have a get together and last second we decided we wanted it to include a trolley. I emailed Thomas at Second City Trolley and he emailed me right back. Within 24 hours I had a trolley booked and paid for - costumer service. Night-of, our driver, Doug, could not have been any more professional, accommodating and patient. We were a hot mess by the end of the night and he was just great -- constantly communicating with me through texts on where he was located and when he would be picking us up. Furthermore, if you're thinking about doing a trolley - do. It's absolutely unexplainable how much fun it was to drink on a trolley or why it was fun but it was great. I will absolutely be contacting Thomas at SECOND CITY TROLLEY for any future trolley needs.

Thomas, I cannot thank you enough - last night was a huge success. Every single person had a great time - thank you, thank you, thank you for: helping pull this together in only a week,and the BEST DRIVER EVER. Everyone loved Doug - there's a pretty big email chain going on between the ladies chatting about what a great time everyone had and Doug has been mentioned in almost every email - patient, nice, courteous - just so great. Looking forward to the next time already! Thanks, J.C

Hi Thomas, I wanted to let you know that I just left you a 5 star Yelp review. From start to finish, I couldn't have been more impressed with your business. Thank you so much. We had an amazing time and I really appreciate how accommodating everyone was. You may have noticed from my email address that I work for LivingSocial here in Chicago. If you ever would like to consider running a deal on our site for Trolleys, please let me know. We would be more than happy to be associated with a brand like yours.
Thanks again! Shannon W

Rachel P. Chicago, IL I rented a trolley for my husband's 30th birthday party last Friday. It was a total success! They let us bring a keg (which I highly suggest, cans get excessive) and even had a bucket for us to use for the ice. Doug was our driver and he was great! About half way through our ride the trolley started making a weird sound (which no one could hear because the music was loud) so after we dropped off a group of people at a bar we exchanged the trolley for a new one. Doug understood this was an inconvenience and allowed for an hour extension of the trolley. This made me like him and the company even more. I have worked many events and most of the time you have to talk to a manager or something to get any type of reimbursement. Doug made the executive decision and it paid off! We also had a trolley for our wedding, but mainly used it for transportation, not for partying. I would recommend using the trolley for both! It is so versatile. Thanks Chicago Trolley Rentals DBA Second City Trolley and Doug for making my husband's birthday special!

Natalie R. St Paul, MN We had a birthday trolley last weekend, and our driver Mario was exceptional. He called to confirm the times a few hours beforehand, and showed up right on time. We had to make a few unscheduled stops, and he was really patient and accommodating. I left my purse on the trolley that night (with basically everything important in my life in it), and Mario called to let us know that he had it, and then met us in downtown Chicago the next night (while off-duty!) to give it back to me -- a lifesaver. I definitely recommend them, especially Mario as a driver.

Faye A. Chicago, IL We recently used this company and I cannot say enough good things about them. Our driver Nick, called me the day before the wedding to go over and confirm all the details. He informed me of all the accommodations on the trolley (ipod hook up/coolers etc) and showed up on time the day of the wedding. The trolley was where it needed to be after leaving each site. When booking the trolley, I made a mistake and booked it for one hour less than we needed. Nick politely informed me the morning of, and did everything on his end to get us the additional hour, and it turned to be a success. There was a slight hiccup when my card was charged, it was accidentally charged twice. I called Thomas about this and he immediately reversed the charge. Within minutes of hanging up, I received an email confirming that my card was refunded. I could not ask for more - thanks to Nick and Thomas for making the day so great (which included fixing my mistake). I really cannot ask for more when it comes to service.

Trolley Features

  • 25 to 40 Passenger capacity with perimeter seating
  • Speaker Sound System with CD ,iPod and AM/FM radio
  • Air-conditioned and heated for your comfort
  • Perimeter seating for more intimacy
  • Totally enclosed to keep out any unwanted weather