I just used Second City Trolley for my wedding. It was a terrific experience! Their customer service was terrific; it was easy to contact them and reserve the trolley, they were clear in their costs, I called to confirm and everything was fine. We rented the Tango trolley for 4 hours and it was waiting for us when we exited the church. The driver, Ali, was awesome! He had picked up some buckets full of beer and ice at no extra charge! I had previously mentioned that we would have beer and sandwiches that we needed to keep cold, so I knew that there would be ice, but the beer was an added bonus. He drove wherever we asked him to and even stuck around about 10 minutes after our time was up because we were a bit behind schedule. My one caution is the capacity of the trolleys that are listed online. We had 30 people on the Tango (listed at capacity 38) and it was comfortable. We probably could have squeezed 2 more people on the trolley in wedding clothes and managed, but there was no way that 38 people in wedding clothes were going to sit on the trolley comfortably with beer and sandwiches. I think the capacity must include people that are standing. Because we fit perfectly, the day and the trolley company were delightful. I would recommend their service to anybody. read more

Second city trolley was beyond amazing! Our driver, Doug, arrived right on time, was adaptable and accommodating, and made the night that much more fun! The company was also very responsive and informative to calls and emails. I would highly recommend using this company! read more

Best trolley service in the city! I do a birthday bar hopping trolley each year and it's always a hit. The drivers know their way around and are always so friendly! read more

I had a perfect experience with second City trolley. They were trustworthy, honest, timely. It was super easy to book over the phone and they were up front about all the costs and what to expect. Sal was our driver and did an excellent job and had a great attitude. We had the best time, and they made what could have been a stressful experience painless! I would use them again in a heartbeat. read more

I recently set up a barhopping trolley through Second City Trolley and it was a great experience from start to finish. You can book it online, laying out your whole itinerary from start to finish. I'd never set one of these up myself, so even after booking I had some random follow up questions like "what's the music setup like?" (stereos and a supplied auxiliary cable to hook your ipod up to), "are there coolers onboard?" (yes), and "do I need to provide ice" (no, or at least my driver was nice enough to provide it for us); and I was able to email them and get pretty rapid responses. The night of the event, my driver was very friendly and made it clear that he was willing to do whatever we wanted--whether we wanted to stick to the itinerary or go off schedule. He made sure we didn't leave anyone behind and took us all over town on what was a surprisingly smooth ride. I really wish I could remember his name, but let's be honest I don't remember much about that night! Great service overall. read more

I looked into this company for getting a trolley for a ride between my wedding ceremony and reception. We didn't want anything too special (i.e. some white trolley with carpet and curtains and other frilly details). We just wanted a clean trolley with working speakers to play music and hang out on. So I said I wanted the bar-hopping trolley and that's what I booked - because they charge DOUBLE for a "wedding service." Any intelligent consumer who doesn't want the extra frills would book a regular trolley. When I called to confirm the trolley a few weeks prior, they sent me this email after we spoke: "We asked directly if this was for a wedding service and were told that this was for a casual event. Because we were decieved we cannot honor the reseravation that you placed and will be refunding this deposit and canceling your reservation immediately. Unfortunately I do not feel comfortable making another reservation with you for this event at this time." This is total BS. I'm sorry I don't want to pay double just because this is a wedding. And I dont want your silly "wedding trolley" .. I just wanted a standard trolley that you'd expect for a private event. So either you're ripping off people because you know you can for a wedding... OR you're shafting people with the broken/crappy trolley who book for something "more casual". I would NEVER recommend this company. read more

I have been avoiding this post because I hate writing negative reviews. This one is especially painful because it affected my wedding day. But I feel I need to warn all the Chicago couples out there who are thinking of booking with them. We reserved a trolley from this company for our June wedding and were impressed with the availability so late in the game (I think we booked it a month before- should have taken that as a bad sign that any trollies were available). It showed up to the hotel on time and off I went with my bridesmaids and parents to the ceremony. You know, about to get hitched. We even had it come early so that we could drive around the neighborhood for a bit to build excitement. As the trolley was pulling onto 94 (not sure why we took the highway in the first place, we were only going to the very next exit), the trolley DIED. On the ramp. Now you might say this wasn't the trolley company's fault, which it wasn't I suppose. But, they were not able to get another vehicle over to us for 45 minutes. I, the bride, was late to my own wedding. Over 30 minutes late. I never had the "this is it" moment with my mother. Or a final celebratory drink with my bridesmaids. We were all too rushed because this pushed back the ceremony, which pushed back the pictures, which caused us to completely miss our cocktail hour which we had planned on attending. (You might ask why we didn't call cabs to just get to the church on time... Well, we tried, but none of the cab companies would stop for pickups on the highway. D'oh!). We left for the honeymoon immediately and were determined to deal with this when we got back. While we were gone, I received a voicemail from the owner, Robert, offering a measely $200 refund on my $800 rental fee. I thought that was a joke. Surely, they should have offered a full refund for the inconvenience they caused. This is the real kicker - my husband and I tried calling many, many times to sort this out with Robert and he was NEVER available and NEVER returned our calls. We didn't even get the $200 refund he promised! Completely lousy service. I would never book with them again or recommend them to anyone we know. read more

A friend and I put together a 30th birthday party and I am so happy we went with Second City Trolley! I have never planned something like this before and their communication was great and was able to answer all my questions. I had received a quote from them for a 28 person trolley and when I went to book the prices had gone up due to a new liquor tax. They waived the fee for me since I wasn't initially quoted with that additional cost. The day of our party the trolley arrived early and our driver Ari was great! He knew his way around the city very well and was able to drive us around to our locations in great timing while also maximizing out time on the trolley. I would definitely use them again! read more

I have to say. Having the trolley roll up to pick us up for our wedding day (07/30/16) was probably one of the biggest highlights of the day. That and walking down the aisle to get married of course! Hah! Our driver, Doug, was amazing. He was so patient and understanding when we were a little behind schedule. There was even bottled water and beer that he offered to us post-wedding! Loved it. Would highly recommend! read more

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 and Doug for making my husband's birthday special! read more

I never used this company for their services, but had the joy of my parked car being hit and run by one of their buses this year. The reason I know it's their company is that a bystander took a video of it on their phone and left me a message. He then sent it to me and we tracked down the license plate. After communicating with the Owner (Thomas Ax) on dozens of occasions he never would provide insurance information to me despite admitting that the bus was his per the license plate. He eventually stopped returning my calls and e-mails. My insurance company eventually tracked down their policy number because it was in a database since they had previous accidents on file. I strongly recommend not going with a company like this who has a dishonest Owner who will not fess up to wrongdoing. I would have filed a criminal charge against the driver, but the bystander never got a visual on the driver. They scratched the entire left-side of my car, costing over $3,000 in damage. I eventually (after a month and a half of almost daily communications with insurance, leaving messages, etc) got the claim processed and their insurance charged. THERE ARE PLENTY OF TROLLEY/BUS COMPANIES IN CHICAGO. PLEASE DO NOT USE THIS ONE! THEY MADE MY LIFE A HELL FOR OVER A MONTH TRYING TO GET MY INSURANCE CLAIM PROCESSED. read more

Chris was our guy! I didn't know exactly what to expect but the trolley was clean and exceeded my expectations. We had a great time, the most fun I've had in a while and afterwards everyone kept complimenting me for deciding to get the trolley. I recommend second city and Chris as he kindly adjusted to sudden stops and was very professional. read more

We recently used Chicago Rolls Royce Limo AKA Chicago Trolley Rentals 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. read more

I made a last minute reservation just 6 days prior to my Trolley event date, and Rolls Royce ( AKA Chicago Trolley Rentals) had availibility still when the other few Trolley rental companies in Chicago were booked- so I took a chance and booked a reservation online over the weekend when their business offices were closed. I like that they had their rates on their website already so I could make a quick decision, unlike other companies that send you a quote within 48 hours. I didnt have that much time to make a decision to wait for a quote. I was pleased overall with everything- our driver John was great, helpful, accomodating, patient, was able to focus on driving with loud party music playing on the trolley- lol- which amazed me even, b/c I could barely hear myself talking to other party goers! the trolley itself was cute- had a victorian couch in the back to sit on which was fun to have besides wood benches! The driver brought a huge round plastic tub for us to use for drinks and ice which was nice and easy option that didnt slide on the floor or tip over etc. My only concern I would pass along- is that this company is not thorough at explaining all the details of your trolley rental in any document, and their website info is at best very basic. So you you must make sure to ask a millions questions yourself by calling or stopping in. Other trolley rental companies have you sign a lenghty contract that lays every last detail out for you- but Rolls Royce doesnt do this. So be certain to ask questions about everything. I've never rented a trolley or anything of this sort before- so I was worried they would be very strickt after my event and try to overcharge me for extra things- like missing an empty cup under a seat while cleaning up after the event or by over extending our time by a few minutes while we cleaned up- but they didnt at all!! Although I did make a point to clean really well after our trolley ride ended and explained this to the driver so he knew. Also, be aware they will bill your credit card in advance for the remainder of your balance due after already paying a large deposit upfront- and without notice and in advance of your event. There is nothing that says this on any of their documents, emails, or website, although it was described to me as being "standard practice". I hope they will be more upfront with this rather important detail with future reservations. So just be certain you ask alot of questions when you make your reservation like i said- They were however very quick and accomodating with every request I made, answered every question I had and we ended up having an overall great experience with their office staff via phone calls even if they did come off as being a bit too nice in that fake-nice way ( for those of us who have worked in customer service before, and dealt with an unhappy customer you know what I mean!), and we were sooo happy with our driver the night of our event. I think our event was a success, my little sisters b'day party trolley was crazy fun and our driver John was so nice about everything, Really. I'm pretty sure our group was still on the mild side compared to some others who rent the drinking trolley package- but I still want to give a BIG thanks to John our driver for everything!! My little sister had a blast at her first adult birthday party as a civilian again- she recently completed 6 years of service with the Marine Corps, where last year in 2010 on her birthday she was deployed to the Middle East- so this birthday was extra special for all of us who got to spend it with her and Rolls Royce Trolley Company did a great job makings sure she had the greatest birthday Trolley party ever! read more

We booked Second City Trolley for our October 19th, 2013 wedding in downtown Chicago. The communication and professionalism was very good, which lead to a wonderful experience. We rented the 737 trolley which is specifically used for weddings only, which was nice that you didn't get a trolley that had been used the night before for a pub crawl. The driver the day of on time (in fact early) and was very courteous while in the trolley. He even hung our "Just Married" sign on the back while we were in the ceremony. Afterwards, we got charge an accidental overtime charge, but when I called, they reversed it without question. Overall, I would recommend Second City Trolley to anyone! read more

We used Second City Trolley last Saturday for a bachelorette party. Mario was our driver and we could not have asked for better service. Mario called me in advance to confirm he would be our driver and made sure I knew he would have an aux cord for music if we chose to bring it ourselves, garbage bags and large tubs for drinks. Mario then even offered to fill the tubs with ice in advance so we would not have to worry about carrying them out from the hotel. The trolley was spotless and had more room than I had ever seen on a trolley. We requested one final stop last minute that we knew would put us slightly over the time frame and Mario was happy to get us there to make our day complete. Great service! read more

Booked trolley for my daughters 25th Birthday. Called ahead before booking online to clarify questions etc. Talked to Tan. Put down deposit & said we would pay balance in cash. Received confirmation email & email requesting itinerary. Sent itinerary & on day of event driver called when on way. We started a little late to our fault but driver Jim said no problem. He was not given any instructions other than drive around for 1 hour ( we paid for 2) & drop off address. I told him route & stop that I sent to main office, also time & location of end point. He never got that from office. Security guy was also named Jim & OK, a little rude but... Trolley left & drove to first stop not following route we planned but ..OK we were fine. After stop again driver did not follow route & with @ 45 minutes left pulled over to side of road & sat there for @ 15 plus minutes while Jim Security guy was on phone. When asked what problem was he stated they were not paid & wanted balance $$. My son was on trolley also tried talking to him & he said I am not talking to you I am talking to her pointing to my daughter. My son tried explaining he had the $$ etc but Jim would not listen They gave them balance due $$. The driver then proceeded directly to drop off point arriving early. Turned down music & again they parked at corner from venue. When asked why they stopped again Jim the driver said too much traffic we will wait here. They would not turn music back up & last 15 minutes was sitting on trolley. With 5 minutes left Jim security guy started yelling at everyone telling them they needed to get off now. They were trying to collect belongings & cleaning up but he told them get off now or else! Absolutely POOR communication with home office & driver. POOR communication with us!! NO ONE ever told us $$ was due at start point. All they had to do is ask. Driver should have come prepared with itinerary. I wish they would not have tipped security guy a dime & he collected the $$ so I wonder if he even shared with driver. He was that much of an A**! If I ever use them again I will make sure not to have Jim & Jim assigned to my trip! read more

I don't typically write reviews however the service I received from Second City Trolley and our driver for the night, Ali, was absolutely TOP-NOTCH. Ali was able to amaze us with some very epic sights and scenery of the city. He was very polite and accommodating to our group. He had impressive customer service skills and was able to win over everyone within our 20 person group. I recommend Second City Trolley and Ali to anyone looking for an affordable way to celebrate your birthday in very memorable way. read more

We used Second City Trolley for our June 15 wedding. We booked the Orlando Trolley and it was clean and photographed well... perfect for wedding photos. Our driver was great. I can't remember his name but he was very nice and excellent at navigating those oh-so-narrow Lincoln Park side streets. He was on-time and knew how to navigate the city and avoid traffic jams. Price was a little on the spendy side because the trolley is air conditioned, but I was willing to shell out $200 to not be sweating profusely in my lovely gown. Overall, they gave top-notch service and I was very satisfied. Highly recommended! read more

We rented a 25 person trolley for a bachelorette party last night. It was perfect! The driver, Gus was so friendly and was so accommodating to our schedule! The whole process from booking the trolley to actually having it pick us up and eventually dropping us off, it was a great time for the bachelorette! Thank you so much! We will defiantly be using you again! read more

Booked them for a corporate event and they NEVER SHOWED UP!! We were left scrambling for cabs at the last minute during rush hour for 32 people and it turned into a nightmare. The kicker is they never called to let me know the trolley was not going to show up. I called when the trolley was late and was given a bit of a run around until I finally just said we would take cabs in order to not miss out on the corporate event that I had spent months planning, and that we were all late for!! The man I spoke with on the phone said that he would send another trolley but it would have been at least an hour! We would have missed over half of our corporate event at that point. The customer service was absolutely horrible! I cannot in good faith recommend them. I was later told, by voicemail, that our driver was hit by some one that ran a stop sign. Accidents do happen but when you have a contract in place with a corporation you should have a back up on hand instead of leaving us stranded and telling me it would be there when it gets there!! No one even followed up to try to reach me in person to apologize instead I only received an email and voicemail. Thomas did try to call the next day but we were disconnected and he did not call back. They refunded my money but I was still completely dissatisfied with the way that they treated me and very upset that they ruined a corporate event. I will also add this was the second company I tried to get a trolley with. The first company, another big trolley comp in Chicago, also flaked on me the day before and I was originally so happy that Thomas was able to take care of our transportation. I think I will just stick to limos and party busses from now on..lol read more

The customer service I received from Second City Trolley was amazing from start to finish. Email reply to my numerous questions were prompt and patient. They were very accommodating, allowing us to choose a time frame that was not one of their standard options in order to fit our needs. Scott, our driver was great! Friendly, prompt and so well prepared ... he had umbrellas and a wine opener for us to use which was great because we had forgotten both! The trolley was clean and spacious. The sound system was good and the temperature was comfortable. I would definitely recommend Second City Trolley and will not hesitate to use them again if the need arises. read more

I called around looking for the best price. I spoke to thomas from Second City and he was very pleasant. I was sold. All other offers could not compare to how polite and informative he was. The driver was on time for pick up and drop off. Knew exactly where to go without any direction from me. The trolley ride was for a corporate event so it needed to be flawless and it was. read more

Trolleys in Chicago are the absolute best especially with Second City. Our driver Jack was so friendly and accommodating. He maneuvered through areas like it was a breeze and always made sure we were doing okay. It was the little things as well that made him a professional. Pulling up in front of the door as we started to pour out and helping to clean between stops. I will definitely use this company again. $25 a person for 3 hours was well worth it! read more

We booked them for a bachlorette party. Booking was easy and the day of they arrived early and were very accommodating. I would definitely recommend them! read more

If you are looking to book the best and most affordable trolley in Chicago, look no further. From booking to the actual trip, Second CIty Trolley went above and beyond to ensure everything went smoothly. I was booking a bar hopping trip from the other side of the country and Second City Trolley did everything to ensure I felt taken care of. Our driver was Brian and he was THE BEST. We were a large group of rowdy women and he handled it like a pro- super professional, giving us trip advice and taking us around the city. We couldn't have had a better day- Second City Trolley made that happen. BOOK WITH THIS COMPANY- you will not be disappointed at all. read more

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. read more

My friend and I used Second City Trolley for our birthday trolley crawl over Memorial Day Weekend. Everything was fantastic from booking through our last drop off point. Our driver, Ali, was friendly and accommodating. The customer service was excellent and they even allowed us to shift our start time from 7pm to 8pm, once they confirmed that no one else would be using our trolley for the later time slot (10:30pm-1:30am). All of our friends had a great time and I will definitely be booking with them again! read more

We booked Second City Trolley for our wedding after reading such great reviews on Yelp. The quick version of our experience was that the communication on their end was minimal to non-existent at times. I had to re-send an email three times and make a phone following up over the course of two weeks to get a response, and that was after we had already paid our 50% deposit. The email was to confirm our pick up times and schedule as we had three trolley booked. I also had to follow up multiple times to find out when exactly we would be charged our final payment. After working with numerous vendors for our wedding, Second City Trolley was the most challenging leading up to the actual wedding day. In a sense it was almost too relaxed. The wedding day itself is where everything went really well. One of the drivers went above and beyond to make sure our day was flawless. The AC worked really well, the trolleys were clean and the drivers were as charming as could be. Basically if you are a planner and like communication (a response in return for an email), this is not the company for you. However, the end results were great and we had only positive feedback the day of which is why they get 3 stars instead of less. read more

We used second city trolley for a bachelorette party and had an excellent experience. Definitely request Scott--he was great!!!!

I booked a 35 passenger Trolley with Second City for a friends going away party. I've dealt with many Trolley companies around Chicago and they are by far the best. From booking to the event, it was perfect. Our driver took us wherever we wanted and were extremely flexible with our rowdy group. BOOK with Second City if you want the easiest and most flexible company. We had a blast! read more

My husband and I got on married on the hottest day of the year this year where it hit a sweltering 95 degrees. We knew it was going to be hot, so we ensured Second City Trolley would have an air conditioned trolley for us. We had no complaints with the trolley - until the a/c completely blew out on the way to our ceremony. At the time it was terrifying, but now we can laugh about it because it will be a memory etched in my head (especially because it sounded like gun shots). Luckily, we only had to sit on the trolley about 10 minutes without any a/c and the company immediately switched out the trolley for a new one with air conditioning. The driver stayed calm and collected throughout all of this and then got us to all the spots we needed to be on time. Despite the a/c fiasco, I would still recommend Second City as we've used them in the past and had no issues. They are extremely professional and undoubtedly the best trolley company in Chicago! read more

Great business! Thomas is a good guy and runs a great company. I would recommend Chicago Rolls Royce Limo to anyone looking for transportation services. read more

Booked a trolley with Second City for my boyfriend's birthday party this past weekend and once again, had a great experience with them. Quick to reply, friendly, helpful, and our driver, Mark, was awesome!! Thanks again, Second City! read more

We had a great time. Ali let us play all our tunes a max blast, he drove us around for a good amount of time between bars, and was super nice. A friend left a phone on the trolley and we checked in that night with the company and he said they would check for us at the end of the night. Got a call and met them to pick it up the next morning. Good rates, great trolley - would totally use them again. read more

We had a pretty complicated time line for our two drivers, but they pulled it off! Price was right, they are local, and drivers were very friendly. read more

Highly recommended if you've got a big group.

I have used Second City Trolley now for three separate events, and it has always been great. Not only are they extremely flexible due to the large fleet of buses they have, but the buses have always arrived clean, on time and without any issues. The drivers have always been very nice, and Dale has been very great to work with and always very responsive to all emails. I have switched up the size of the trolley with a days notice, and they have always been very accommodating. I will definitely be using them again in the future! read more

Absolutely will be booking with Second City Trolley again!!! I used the trolley for my sister's bachelorette party of 13 ladies. When I was first looking to book, I really wanted perimeter seating and the trolley that arrived was perfect. I had many questions that I emailed to The Trolley Man (that's his actual title and signature) between booking and the event and he answered all of them promptly, usually within the hour I emailed him! The driver, Brian, called me 30 mins before arrival to give me an ETA and when he arrived, he helped load up the booze, plus he had a tub of ice ready to go. We blasted our music, compiled on my sister's iphone and danced the whole three hours, with a quick stop at one girls house for a bathroom break. It was an amazing night and cannot say enough about Second City Trolley and Brian, our driver. Thank you! read more

We used Second City for a bachelorette party this past weekend, and what a great experience! Communication was easy and clear, pricing and expectations were known upfront, and our driver, Doug, was extremely kind, courteous, and prompt. The trolley itself was cool and they provided coolers and water for guests to use. AUX hookup made it easy to play our own music, as well. I would absolutely recommend using this company for a trolley event. They were great! read more