We used Second City Trolley for our Wedding day and it was an amazing experience! Communication before the day was great and our wedding ran seamlessly with their help! Would 100% recommend! read more

Booked them for our wedding. Initial inquiry, booking and confirmation was relatively painless. I actually didn't know who I was communicating with because it was never signed but my emails were always answered and my planner was able to get a point person for day-of communication. As an aside, renting a trolley for any other occasion than a wedding is SO much cheaper but because it's a wedding, it's automatically 3x the cost, which is kind of insane but we got pretty consistent quotes from a lot of different companies and trusted Second City the most based on our reviews. For our wedding day, the trolley was air conditioned (big concern of ours) and big and spacious, as discussed, to house our crew appropriately. The trolley did arrive early / on time but where we took off some stars were that 1) we left the hotel a little later than planned and our photo timeline was tight so we had some panic when immediately upon leaving, our driver took the wrong turn which added 10-15mins to our travel time to our first stop bc of all the downtown traffic and one way streets, 2) he jumped several curbs - when we stopped at our third stop for bar pics and when we got close to the venue and 3) when we got to the venue and circled a bit before it was decided that the streets were too narrow to get through so he'd have to drop us on Clark so we can walk everything in. I feel like drivers should be aware of the stops and already have routes and exits in mind and I felt like both my planner and photographer were having to direct him. Other than that, think good service leading up to our wedding day but it really depends on who your assigned driver is and how prepared they are. read more

Great communication, reliable and easy to work with (had to change our wedding date due to covid). Very accommodating, timely and professional. Booked the Sophia trolley for our wedding and couldn't have been happier. The trolley experience was great from start to finish especially since it was raining sideways on our wedding day! Our driver made sure that he parked as close as possible to the entry/exits to avoid us getting soaked. Would definitely recommend booking the Sophia trolley for a large wedding party or group. Thank you Second City Trolley! read more

Second City Trolley - Photo by @annkamphoto - Party Bus Rentals Near Me - Chicago, Illinois

I had a wonderful experience with Second City Trolley. I recently booked a 30 person trolley for a birthday, and the company was informative, helpful, and quick to respond to any questions or accommodations. The trolley arrived on time, was clean, and our driver was awesome. I highly recommend Second City Trolley to anyone in Chicago!! read more

Our review from 9/7/19 Thank you for the wonderful experience with Second City Trolley! Everything- from booking the trolley, confirming our appointment, and attending our appointment- went very well. Everyone we spoke to was very patient and friendly. Our driver, Ian, was lovely. He was very patient and flexible. He drove safely and maintained a genuine smile throughout the evening. We sincerely appreciate him. My sister and all of her guests had such a fun bachelorette experience. I cannot thank you all enough for the unforgettable time. Thank you! read more

My husband and I reserved a trolley on our wedding day for the wedding party. They picked us up from the church, took us to our photo spot, and drove around for a bit before dropping us off at the reception. This company was reliable and extremely accommodating to all our requests! They even made an extra stop to drop off our photographer. Trolley was very clean and the driver & security guard were friendly. The trolley itself was a great addition to our wedding photos! Highly recommend Second City Trolley. read more

Second City Trolley - Party Bus Rentals Near Me - Chicago, Illinois

It was an absolutely amazing experience, Scott took the time to go over the inintery with us before we left to make sure that we spent ample time on the trolley as well as have enough time to hop off at the wanted stops. He really knew how to plan a route, knew when we needed to stop for the bathroom and knows how to take the most amazing group picture! I cannot say enough positive things about him, he really made the whole experience 100% perfect. I just wanted to let the company know how great he was. We would definitely book with him again! Thank you Scott! read more

Booked them last moment and they were AMAZING! They stopped everywhere we wanted and even had an aux cord bc we totally forgot ours. 10/10 you should rent a trolley from them. read more

Awesome experience. Driver was so flexible and adapted to some street closures. I would book with them again in a heart beat.

Don't look anywhere else to reserve a trolley in Chicago. My girlfriend recently booked a 38 passenger trolley for my birthday party, which I then turned into a proposal before the rest of the party hopped on. From the driver, Scott, to Doug back in the office, the customer service was incredible. These guys were fully on board with my plan to propose and went above and beyond to ensure it went well. I probably talked to Doug six times during the week and he couldn't have been more responsive and helpful. The night was a huge success. I highly recommend Second City Trolley and will be using them for any future trolley nights. read more

I booked this trolley for my friend's bachelorette party. It was a wonderful experience! Our driver, Tom, was extremely helpful. He called us before the event to confirm all of our details. He helped us load the trolley with our ice and drinks. He also took us to a few really scenic areas in Chicago, so we could take photos with the bride. At every stop, he helped the ladies get on and off the trolley safely. The trolley itself was very clean and spacious. We rented the 25-passenger trolley. It had an awesome open balcony-like area in the back. We had more than enough space to walk around and dance while Tom drove us through the city. It was amazing to be able to party with the city as our backdrop. The bride-to-be and guests had a wonderful time. I hope I have an opportunity to use their services again! read more

Second City Trolley - Back of the 25-passenger trolley in the balcony-ish area. - Party Bus Rentals Near Me - Chicago, Illinois

See all

Second City Trolley saved the day! We hired a trolley from Second City plus a few other vehicles from a different vendor for our daughter's wedding day. The other vendor had one vehicle running late, potentially causing major issues with getting to the ceremoney on time and another vehicle canceled on us last minute. Second City was there to help us get through the day and generously provided extra trips to and from the venue to help us get our guests where they needed to be. The driver was so friendly and kind, the trolley was clean and the A/C worked great! Communication when booking and confirming was excellent. Highly recommend! read more

second city trolley is the best trolley rental service around. The drivers are friendly and professional, the trolley itself is spacious and easy to navigate. I would highly recommend the company, especially the amazing Doug! I use this company at least 4 times a year and only once made the big mistake of trying another company. Always choose second city if you're looking for a fun time! read more

We hired Second City Trolley to provide transportation for our wedding party on our wedding day. Second City was easy to coordinate with, even when I made some last minute changes! We had so much fun riding around the city to different photo locations. It was a great way to celebrate with close friends right after the ceremony! I definitely will be using Second CIty Trolley for events in the future. read more

We can not say enough great things about Second City Trolley. This is the second time we've used them and have had wonderful experiences both times. We were especially impressed with their prompt response when we called to book a trolley the day before we wanted it. They got us all squared away in 24 hours! Our driver was awesome and told us he only had one rule - to have fun... what a legend!! We had a passenger leave a credit card on the trolley and they even mailed it to her afterwards. Thanks again Second City Trolley for a great time. read more

I used Second City Trolley for my wedding and it was my biggest mistake I could have made. My husband and I went to look at the trolleys beforehand and everything seemed fine. They called me the day before to confirm the times of pickup. My ceremony started at 1:00 pm. The trolley was supposed to pick up the groom and groomsmen at 12:00 pm and then come get the bridesmaids (it's a 7 minute drive between both houses). Well at 12:15, I get a text from my almost husband telling me that the trolley had not picked them up yet. I call the company and they tell me 10 minutes. Well now it's 12:40 and no trolley. I'm in tears, this is my big day, I only get one and wanted it to be perfect. My brother calls the company and the man laughs at him. Now my dad is calling them and they tell him something about graduation parties. I'm sorry, but a wedding is way more important than graduations. Never once did they apologize that they were late. Now it's 12:50 and my dad calls the company again and they tell him the trolley just left the city (it was to pick up first in Lemont). Now my groom and the groomsmen scramble into cars to get to the church. Thank God I had a limo that was supposed to only take myself and my dad. All 7 of my bridesmaids had to squeeze in along with myself and dad and get to the church. My ceremony starts late and the trolley finally made it to the church. I paid for 5 hours for this trolley and only used it for about 2 hours. I'm giving one star because thanks to my dad, I was able to get some money back (should have been a full refund). They knew this was for my wedding. They knew my ceremony started at 1:00 pm and they knew where to be. (They called the day before to confirm everything). There is no excuse and they really ruined my time that was meant for just myself and my dad for the drive to the church. read more

The company gave us a "impaired" driver that was not in any condition to be driving a trolley that was filled with our family and closest friends on our Wedding Day. We had to stop and have someone from the shop meet us and "relieve" our driver. That's all I have to say about that. read more

I booked a trolley for my soon to be sis n law's bachelorette party! I communicated with Thomas for the planning part. He was so nice and was very easy to work with when I had questions or changes in our plans. We rented a 25 person trolley and it was perfect, roomy enough to walk around through but intimate enough we could take pictures, laugh, talk and not have to scream at each other. Salvador was our driver!!! He was amazing! He showed up on the dot at 10:30pm and single handed placed all of our drinks and ice into the beer tubs and coolers. He had called me earlier in the day to confirm pick up location and asked questions about the night we had planned. He was very knowledgable about the streets in the city and when our plans changed he moved fast and without hesitation. My sister n law, at the last minute decided she did want to do the museum tour! In a blink of an eye, Salvador said "it's so easy, let's go!" In the end we were so glad we did, we took some cool pics with the city behind us. He even took pictures for us of the group! We were able to play our iPods from our phones, but really the mix he had playing we were happy with and the sound was great! After driving around awhile and not having stopped yet he swung through a gas station and we were able to have a pit stop. During the time we waited for everyone, he chatted with us and he was just a great guy! A big thanks to Salvador for putting up with 15 tipsy girls who threw out their original plans out and just went with it. I hope he sees this because at the end my bachelorette said in a tipsy voice "can we do this next weekend too" He definitely contributed to her fun! When he dropped us off he hugged us and told the bachelorette "congrats" he looked sad to leave us!! Haha, and with a wave he was gone! Great customer service!! Beginning to end! read more

Second City Trolley - Our trolley! Best time ever! - Party Bus Rentals Near Me - Chicago, Illinois

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. read more

I was finally able to use this company for my party! Best decision ever!! I can't recall the owners name but he was a pleasure to work with. The trolley showed up on time and was so much fun! We had a group going from burbs to Cubs game for a 50th Birthday party. I was a little surprised that my friends were so rowdy. I wasn't expecting the older crowd to get so out of control. Our trolley driver Mark was able to nicely keep all of them in check and keep the party on schedule. Mark was amazing! I'm not sure how that poor man deals with partying people 24/7! He and the trolley were the highlight of the party and helped create lifetime memories for us! We can't wait to plan another party with them! read more

I'm not one who really loves a bar crawl, so when I was asked to organize one I wasn't really sure where to start. We had a great experience with Second City Trolley. Our driver, Eric, was friendly, prompt and (most importantly) patient! I can't imagine being at the helm of a vehicle full of drunks like that. The trolley was clean, the AC worked, the sound system was just loud enough. Reservations were easy, and customer service was excellent. read more

had this trolley over the weekend for a 30th bday. The bus driver was very nice and accommodated all requests. My drunk buddy even left his keys in the trolley. The driver called us back, and a made a trip later that night to drop it off (in his own car). What a nice guy...we'll definitely be booking again. read more

I've never booked a trolley before (but have drank on them aplenty) so I was a little nervous about setting up an event for Saturday June 16th. Seems like the most often used trolley service is Chicago Trolley and Double Decker so I called 2 weeks before the event and was disappointed to hear they were all booked up. Well, it turned out that this was a blessing in disguise. I did more research and found Second City Trolley. Not only did they have plenty of trolleys in their fleet available at all different sizes, the staff was awesome! They walked me through the reservation process and made it so easy. You're required to put down a deposit and pay the rest to the driver (excluding tip, if you wish). They will call you to confirm pick up and drop off times the day before. We had Keith as our driver. Right off the bat, he was pretty incredible. He could have easily been like 'great, another bunch of drunken assholes' but he wasn't. He laid out the ground rules and just wanted us to have fun. He drove us around for 3 hours wherever we wanted to go, at times we (pretty intoxicated) would tell him to drive up to wrigley only to change our mind and tell him to go back where we came from. He never complained. A few things that stood out to me that put Second City Trolley above Chicago Trolley and Double Decker: 1. Right when we got onto the trolley, some of the party asked me "did you get us the Cadillac of trolleys?" Our trolley was nicer than most/all of the trolleys I've ridden on with CTDD, with rows of seating instead of just along the outside. This let us sit closely and drink heavily with out having to shout from end to end. 2. They let us bring an entire keg onto the trolley! I was always told this is a big no no with trolleys, but apparently that is only a CTDD policy. As long as you are responsible, I'm pretty sure you can bring anything onto these trolleys. The keg was a great idea and a money saver. We also brought a beer bong. **They are very accommodating for you to come in after the trolley ride to pick up your keg and other belongings. Although they are located a little far, about 30 minute drive from the city, this is obviously essential to get your deposit back for the keg. Very cool! 3. The sound system was great. I note this because I've been on multiple trolleys with CTDD that the sound system just sucked. Lots of skipping and/or static. We had no such problems and Keith was more than happy to blast our annoying songs (Call Me Maybe multiple times would drive weaker souls crazy). 4. Second City Trolley was about $50 more expensive that CTDD, but this did not require us to clean the trolley afterward. Often times, other companies will charge a cleaning fee afterwards so it was pretty much a wash. Definitely worth the extra cost, only a few extra bucks per person. Overall, the party was a success and everybody loved the trolley! Next time I need a trolley, I will for sure be booking with Second City and requesting Keith. Thank you to the entire staff! read more

We just celebrated our wedding on Saturday, July 26th with Second City Trolley getting us to and from the church in raucous style! My wife and I were scrambling for a trolley two weeks before our wedding and Thomas was able to accomodate us with the Iowa trolley that fit up to 30 people at a reasonable price. Thomas was very prompt and courteous at getting back to us. We were lucky to have the Iowa trolley since we used every inch of space. The driver Nick was very prompt and an excellent driver. He had the difficult job of manuevering through the busy streets of downtown Chicago and did it with clear expertise. Again, Nick was on-time and even filled the two coolers available on the trolley with ice for us. Not that he offers this service as well, but Nick was kind enough to run to the store for us to get us two more cases of beer! He was a lifesaver! The audio hookup in the trolley was excellent as well. Again, I would highly recommend Second City Trolley if you're planning a special event in the future and need prompt and second to none party transportation. read more

Great great great! As Demetrio stated, their office is a bit odd and might make you think twice about wanting to use their service- don't! I used them for my bf surprise birthday party for just a pick up drop off. They were great with offering a fair price and showed up right on time. I had planned to have champagne for the ride. I sent my father and father in law to retrieve the case of champagne and put it on the trolley. As unbelievable as it sounds, there was another trolley parked in front of my house. The dads put the case on the trolley but it turns out it was not ours! After we realized what had happened our trolley driver (I cant remember his name) stepped out of our trolley, in the pouring rain, to make phone calls to try to get our champagne back. Turns out the dads had put it on a different Chicago Rolls Royce and Limo company's trolley. That trolley, that was filled with passengers already, turned around to deliver our case of champagne saving our birthday toast! I cant say more positive things about this company. I will use them for any and all of my trolley needs! read more

From scheduling to the actual trolley ride, these people were great! Doug was very helpful during scheduling and our driver and security guard were great sports - looking forward to using them again. read more

The wife and I used Chicago Rolls Royce for the rental of a trolley for our wedding. Overall, it went okay. First, the reservation place did not look like a rental office, but is in fact in a space of a former car repair shop. Weird, but eh, it is what it is! As for the trolley, it was a little older, and they did not use the trolley we chose the night of the reservation, but a much smaller one at that. The trolley was a little cramped with the smaller one, I didn't complain but all in all the night went well except for that change. They were prompt on being at the hotel at the specified time for pickup, and did a good job driving us from location to location to take pictures, then finally bringing us to our final destination at the reception. Overall, good service, okay prices, okay trolleys (except for the last minute switch-a-roo.) read more

Hired Second City for a bachelorette party. I was planning from San Francisco and to be fair, Second City was far and away the best vendor I worked with amidst my planning. Our driver, Frank, was unbelievably professional. He gave me a call a few hours before our pick up and introduced himself, and let me know he may be a few minutes late due to traffic. He did arrive a few minutes late, but he was great about honoring that time at the end. During the ride he let us do our own thing, he was flexible, nice, kind and respectful. Not once did he take his eyes off the road at the debauchery taking place. Props to him. Thank you, Frank! You rock. I highly recommend this company! read more

We used Second City Trolley last weekend for a birthday party. We were in need of changing the trolley size more than once. Thomas was more than willing to help us out and meet our changing needs. The experience overall was great. Our driver was very kind and able to take us wherever we wanted to go. The trolley was exactly what we needed: speakers, ipod hook-up, seating, fun lighting, etc. We'll definitely be using Second City Trolley again! read more

I used Second City Trolley last weekend and it was perfect. Our driver, Carlos, was great. He listened to all of my directions perfectly and even knew of special spots for the obligatory restroom breaks that could accommodate a group of 30. He arrived early and dropped us off a few minutes late, always with a smile on his face. He was a pleasure. The only qualm would be the windows on the trolley only go half-way up, so it was a bit stuffy inside. Otherwise, the actual trip was great. The scheduling staff was very helpful and friendly. The reason I did not give five stars is that we had a slight mix up that almost derailed the entire evening and caused me a brief fit of stress. Fortunately, the crew mobilized their resources and were able to come up with a solution to meet my needs. This really speaks to their ability/willingness to work their customers. I would recommend this company for anyone planning a birthday/bachelor(ette) party in the future. You will be pleased with your decision. read more

Outstanding company with great customer service! They were quick to reply to my request and made our planning process extremely easy. We will be using them for future employee events and highly recommend their services! We couldn't be happier with our selection. read more

I have used Second City Trolley about four times in the past year and this past experience was by far the best!! Obviously we had a wonderful time and the driver Ali was the MAN but the experience with Second City was even better because of how professional they were with the a particular situation of mine. Originally when I booked the trolley I guess I checked a box stating that I was going to put the full charge of the trolley on my card (the same one I put the deposit on). The day of the trolley I collected the money and gave it to the driver with tip included. A couple of days later I saw that there was a charge on my card of $500+ and immediately went into panic mode. After calling and speaking to Second City, they told me that they had noticed the problem and had refunded my money. They even offered to send me a check if I had preferred DESPITE the fact that it was my mistake! The first trolley we took, my boyfriend left his iPod on the trolley and it was returned no problem as well. Moral of the story is that this company is honest and know how to provide a great time! We will definitely be using their services again and are very much looking forward to many more successful rides :) read more

Rented out a huge 30 passenger Trolley for my boyfriend's 25th, this past weekend. It was easy booking, easy confirmation. They were there on time, and the surprise was a success. They were absolutely accommodating for all my requests. I really appreciated working with these guys! Driver was GREAT! Took us everywhere for great pictures, pee breaks, drive with a view. Will use them again. Great pricing, and well worth the money. read more

We used Second City Trolley for our wedding and they were great! I think we had the greatest driver ever who made sure nothing could ruin our day. He went so above and beyond that he pinned a boutonniere on my father when no one could get it to stay on. It was also pouring rain and he took so many extra steps to keep us dry and the trolley clean. He drove over the curb onto the sidewalk to get me as close as possible to the church steps so I would not be rained on before the ceremony. The company is easy to work with and very responsive. read more

I can't say enough great things about this trolley service! We recently used them to host an ugly sweater trolley and it was such an easy and seamless reservation process. Our driver was so flexible with locations and stops which made the night so much fun and much easier to pick up friends who needed to come later in the evening. The trolley came with coolers and an aux code so we genuinely just needed our personal beverages and we were good to go! I would definitely use this trolley service for future events and would recommend them to anyone looking to host an event! read more

I booked this trolley for my boyfriend's birthday. They were great! I booked my reservation through Doug who was super friendly and very accommodating! I even booked it a few days before and they were able to provide me with the trolley size I needed with a great price last minute. Our driver, Mike, was very nice as well. He called to confirm my reservation, and arrived promptly at our pick-up place. In fact he was early! He stopped whenever we needed a bathroom break with no problems. One of the people in our group, lost his keys and Mike came back to return them. The trolley was spacious and clean. They provide an ice tub for all of your beverages to be chilled. This was the easiest, most fun, and efficient trolley company i have done business with. I will be booking all my future trolley events through Second City Trolley Limo!! HIGHLY RECOMMENDED! read more

I used Second City Trolley for my birthday party recently and they were great! Our driver, Mike, was very accommodating and we arrived back at our final destination right on time! The booking process was super easy and they were able to adjust the start time of my reservation for me. So wonderful! read more

I've called them twice and sent 2 emails and NO response. I liked the looks of the trollies better than other companies but how can I trust a company that doesn't return calls. read more

The entire experience from the booking of the trolley to meeting the driver to the drop-off was perfect! Our party had an amazing time. I plan to (continue to) recommend Second City Trolley to all of my friends! read more

Great Staff! Always attentive and informative! I've used them for the pride parade for the last four years! Amazing customer service and always on time! Definitely Go with this company! read more