I must say, I used Second City Trolley Limo for my son Senior Prom & I was so pleased with the services. They really worked with my especially since I was changing the time often. My son impressed his date & his classmates they allowed his special day to be just that his special day. The driver was very pleasant with the guest & he treated my son with respect. I will use them for future events & share my great experience with others. Thanks! read more

I contacted Second City Trolley for a bar crawl the weekend before the fourth. Everything went perfect. The front office staff was very polite and accommodating. They called me a few days before to confirm and Randy (the driver) called when he was on his way. He showed up about 15 minutes early and we all loaded our beverages and group in the trolley. He drove us anywhere we wanted to go including abandoning Lake Shore Drive at the last second (heavy traffic). The trolley was great. It was clean, open, and had a great sound system. All in all, I would definitely rent another trolley from this company. They were professional, on-time, and everyone had a blast. read more

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". read more

I booked a trolley about a month ago for my birthday. The driver was great, he even picked up ice for the trolley cooler before he met us at the first bar. Fast forward a couple of hours and the trolley completely dies in the middle of the street. The driver calls it in and after 5-10 minutes of figuring things out tells me they can send another one. At this point everyone has left the trolley as they don't want to sit on a broken down bus in the middle of the street when it's 25 degrees out hoping for another one to show up. I'm the only one on the trolley at this point so I toss the driver a tip and take off as well. I called the office and explained what happened. I wasn't angry or confrontational at all, I just wanted to see if they'd be willing to refund me for the time lost on the trolley. They remembered the incident and said to call back the next day. I did, a couple of times, and no one answered. I left a message to call me back and nobody did. If you're not going to compensate a customer in some fashion because your trolley broke down, there's not much I can do about that. At this point, it's not even about that. Ducking an unsatisfied customer who's attempting to contact you is really poor customer service. It left a very bad taste in my mouth with regards to this company. As a preemptive response to the representative that will say "you should have just waited for another trolley to arrive," when I'm paying $200+/hour for your service, that shouldn't entail waiting on a broken down trolley in the middle of the street for 20 minutes. Malfunctions happen, I completely understand, but stand by your product and make it right if they do. read more

We hired this trolley for our wedding day. There was a ridiculous mark-up in price just because it was a "wedding" compared to any other 4 hour service. The trolley itself was fine. Enough room for the entire group and ran great. The driver however was incredibly rude! He was not friendly to the group and would battle about making stops to get pictures taken. We basically had to beg him to make one more stop for pictures even though we were driving right past the last place we wanted to stop. I understand we had time constraints for what we paid for, but he wasn't even trying to be understanding or considerate. read more

I used Second City Trolley to drive our wedding party around the north suburbs for pictures after the ceremony, and I truly can't say enough good things about our experience. From the beginning, Thomas responded to my (many!) e-mail inquiries immediately and was very helpful and friendly. The prices really are reasonable with other vendors in the area, and they have a large variety of trolleys to choose from which is awesome - you can look at all the pictures on their website so you know exactly what you'll be getting. It was actually tough to choose because they had so many great options. Our driver, Nick, was superb. As promised, he called me the day before the wedding to make sure we were all set to go and confirm times and locations so we wouldn't have to worry about it the day of the wedding, which was much appreciated, and he arrived at the ceremony site early to be sure there were no problems. The trolley was beautiful, and very clean--you can tell Nick really puts a lot of effort into keeping it maintained. And the A/C worked great! They say rain on your wedding day is good luck, but people, we had flash floods (literally--storm alerts on the phones and all). Throughout the entire ordeal, Nick was calm and drove very carefully through what was really a heck of a storm that turned the streets into rivers. Typical Chicago, you never know what weather you'll get, but he really was terrific and put everybody at ease. I would absolutely use Second City again and wouldn't hesitate to recommend them to anybody else. Thank you for making that part of my wedding planning as easy as can be! read more

I used Second City Trolley for my birthday party over Cinco de Mayo weekend and everyone had a blast. It was an absolute hit and I would recommend this to anyone looking to book something fun for a birthday, bachelor, or bachelorette party. Our driver was Tom and he was super nice! He even helped me load stuff onto the trolley. I can't thank Second City Trolley enough for making my birthday a success! read more

This wound up being a horrifying experience. This trolley had no working air conditioning on a very hot day! And we were taking on-site pictures throughout the city for 3 hours! After we complained, the driver said he could do nothing. I tried to tough it out, just to get through it and try to think positively. Then....it broke down. We had to wait 20 minutes for a new one. They never even warned me before it arrived or asked me if I would like a replacement before the wedding. It was evident there was a problem with the trolley from the beginning. We complained afterward and Thomas admitted all that went wrong, but said they provided a new one in reasonable time. I expected a dependable service, and did not get it. It was hugely embarrassing to be stuck on a busy street in Chicago waiting for a working trolley. I'm disgusted with this company. A total waste of money! Stay away! read more

We used Second City trolley for my mother-in law birthday transportation needs. We had to transport about 35 people 65 and older to the birthday destinantion. Trolley came right on time, so our group did not even have a chance to start worrying; ride was smooth, driver was very courteous and accomodating to some of the challenging mobilities of our guests. Pick up and drive back was as wonderful, too, and it felt like a summer camp bus - people were singing and even attempted to dance! Everybody enjoyed the ride. Thank you for wonderful service! read more

My husband and I recently got married (July 24) and used this company for our wedding party ride. We were so excited to use a trolley, and unfortunately the company ruined that experience for us. We were initially told that the Orlando was available so we planned on booking that one. However, once they received our contract, they said it was no longer available but that they would upgrade us to the Sophia for the same price so we were very happy with that. On the day of, the trolley arrives, and mind you is about 100 degrees that day with the heat index, and there is NO AC. Are you serious?? You send us a trolley on one of the hottest days of the summer and there is no working AC?? Their website boasts that all their vehicles have AC, but if you are to consider them for booking I would make sure that the AC is working, but apparently they don't have the courtesy to let you know that there is no working AC. We were so hot and uncomfortable, it was miserable. They should not onlyu have makde us aware of the situation, but they should have sent us with a different vehicle in that instance. We had grandparents and parents who were unable to ride with us due to the extreme heat on the trolley. So very disappointing. On top of that the driver had no idea where he was going, even though he had a GPS. My husband and I were not able to enjoy the trolley ride due to the fact that we had to stand up there next to him and direct him where to go. I would not recommend this company to anyone given the nature of our situation. read more

I recently used this company when booking transportation for a corporate event. I needed 6 trolleys to do pick ups and drop offs. Everything was flawless! It couldn't have gone any better. The trolleys were all there ontime, and came back efficiently to do another pick up as we had asked. I only wished they would have confirmed with me the day before, instead I reached out to them. But everything was all set, and I had nothing to worry about. I thank them for making sure the transportation ran smoothly! read more

Chicago Rolls Royce Trolley did our transportation for our wedding day. Thomas was easy to work with and was extremely quick to reply to any of my emails. They have a large and unique fleet of trolleys to choose from. We booked the 32 passenger trolley and it comfortably held 28 grown adults and 2 large coolers. The seat against the back wall was a cute antiquey looking couch. The trolley came equip with an I-pod hook up so we were able to make trolley play list while we drove around before the reception. It was a hot and humid day with periods of rain. The trolley had regular windows and air conditioning so that was key. Other trolleys we've had in the past for other weddings had the clear plastic windows and minimal air. The driver arrived at all locations on time (a little early actually) and made all the appropriate stops we needed to take pictures. We were extremely happy with the service. Make sure to tip your drivers!!! read more

I used Second City Trolley for a 50th birthday party with about 100 guests. We got three trolleys and therefore three drivers. All three had fantastic personalities and were totally cool. Our guests were mostly gay men which was a total non-issue for our drivers. I will definitely use Second City Trolley again. read more

Rented this trolley for St Patty's Day and they were a pleasure to work with. Driver was very nice and patient especially considering he did not get a break ... we were on the trolley the WHOLE time and he drove us all over the city only to have us not get into bars! Easy to work with ... great time! One complaint sometimes they are hard to reach via phone .. wish I had the driver's cell phone number a day in advance (but that could just be my "meeting planner anal side talking!!") read more

Trolly owner followed up and professed his sincere apology for the troubles we had for the trolley. Appreciate the follow-up.

I definitely recommend these guys. Rented a trolley for my birthday and had no plans going into it. We brought beer and ice on and just told him to drive. They provided bins to keep all the booze in which was great. The driver was extremely nice. We all had a blast. It was awesome. read more

We loved having Second City Trolley provide bridal party transportation for our wedding! They were on time, the trolley was clean and the air conditioning was perfect for the 90 degree day we had. Our driver was excellent - he had water on the trolley to put our flowers in and a cooler with drinks. He had a great speaker system too which made our ride that much more fun! We would use them again for sure! read more

I think they changed their name to second city trolley, but anyways we used the 25 person trolley service last night for a birthday/bar crawl and it was a great experience. Arrived early, you can bring your ipod, they provide a cooler, awesome driver, overall a good experience with flexible people at a reasonable price. Highly recommended, thinking about renting one every night we go out. read more

I hired Second City Trolley for my sister's bachelorette party last weekend. Our driver was really sweet and we all enjoyed him! We ended up losing about 20 minutes time because an enginge light came on, but the owner Tom was very helpful and even called me himself to reimburse me for the lost time. I really have to commend excellent customer service when I see it because it's rare and would use Second City again in the future! read more

I just threw my husband a surprise birthday trolley and I can't say enough good things about our experience. The trolley was very clean, arrived early, and the driver Ian was amazing and accommodating! I would highly recommend using Second City. read more

We had a great experience working with Second City Trolley for our wedding 5/11/13. They had great communication and customer service during the initial booking process, and our trolley driver (Nick) was excellent. Nick called a few days before the wedding to discuss the plan/itinerary for the day, and was very flexible to the fact that our plans may change based on the weather. Nick was very organized and experienced with accommodating and transporting a large wedding party and even helped the bride/bridesmaids get on/off the trolley on multiple occasions. He was a great driver and was very knowledgeable about driving in downtown Chicago. The trolley was very clean and came stocked with some supplies (two coolers, garbage bags) at no additional charge. We would recommend Second City Trolley, especially for prospective weddings. read more

Another 5 star review, but I gotta say, we had amazing vendors for our wedding extravaganzas. We used Second City for a trolley to take my husband and our wedding guests around for pictures and to our ceremony. Eric drove us without rolling his eyes or getting impatient with us (which he very weld could have). He was a great driver and very punctual. I worked with Thomas to choose the trolley. He was easy to work with and set us up with a brand new trolley. I had no idea what it was going to look like since there were no pictures of it but it was very elegant and had enough room for all of us to sit comfortably. We hooked up an ipod and the sound was really good during the ride. And it was wonderfully well heated! The weather did not want to cooperate with us so everyone was grateful for the warmth of the trolley after each photo op stop. We got a good deal also because we did it during the week. And my Mother in Law said it was very classy (!). Well done Second city :). Well done. read more

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! read more

I used the trolley this past Saturday and have nothing but great reviews from everyone who was on it. Thomas and everyone at Second City were very flexible, polite and extremely helpful. Highly recommended; will use again in the future. Thank you! read more

Really happy with Ali and the entire experience!!! Only (small) issue was that the promised bins were lacking - there was only 1 and for 20ish people we could have used a few more! read more

I used second city trolley for my rehearsal dinner on Friday night and for my wedding day on Saturday. They were punctual and very accomodating! read more

I booked a trolley for my husband's 30th birthday bar crawl. I did research before booking with Second City and their pricing was a little cheaper than other trolley companies in the city. When I called to book, they were courteous, helpful, and attentive. Paying was easy... $289 on my credit card to hold the reservation and another $289 the day before the event. One week before, I e-mailed with questions, concerns, and our itinerary. Within 2 hours, I got a reply with detailed answers. Two days before the event, we decided to change our itinerary and our changes were accommodated easily. The day of the event, our trolley driver arrived TWENTY minutes early. Gus was so helpful and even did the heavy lifting loading the beer and drinks into the trolley. Inside, the trolley was clean and comfortable. Several friends commented that it was the nicest one they'd been on. We booked a 3 hour block of time for which we made 2 stops. Our goal was to spend as much time on the trolley listening to music and dancing. The first stop was at Proust! in Lakeview, where we had a round of drinks and a giant pretzel. When we finished there, Gus was waiting in the trolley and welcomed us aboard as we all piled in. From there, we rode around for 45 minutes and listened to my husband's birthday playlist on the sound system. It was easy to plug his iPhone 6 into the USB cord supplied by Second City. Our next stop was Headquarters for pinball and drinks. It wasn't too busy and everyone was able to get a round of beer before we got back on the trolley for the last 45 minutes of riding. Our last stop was at O'Leary's, where most of the party got out. Gus dropped me off at home where he again helped me unload. The night was a success. I'm so happy with my experience with Second City and highly recommend this company! read more

Booked multiple trolleys with SCT and the first one was an overwhelmingly great experience! Not only was the booking process seamless, but when the trolley arrived it was clean, the driver was fantastic/patient/courteous, and the prices are extremely reasonable! Completely recommend this company if you are looking for a trolley service in Chicagoland! read more

We went with Second City Trolley last weekend when we were visiting Chicago for a bachelor party. We did our research for the best trolley company in Chicago and it held to be true. The trolley was a 25-seater, ample room for our group of 18. Our driver Nick was awesome. Super friendly guy and a great driver. The weather was terrible, but he handled it like a pro. Enjoying drinks on the trolley and seeing Chicago was the highlight of the weekend for everyone. The price was fair and we couldn't have enjoyed it more. Go with Second City. read more

We recently used this company for our wedding on May 21, 2011 to transport our bridal party and friends. The driver appeared unkempt and not very presentable in addition to getting lost on several occasions, even with us giving him directions. For the amount we paid for the service, you think they could at least spring for a GPS! The actual trolley served it's purpose of getting us from the church to the reception. It was not clean or well taken care of and was not what we were expecting for what was being charged. read more

We used Second City Trolley on May 5th for a 50th Wedding Anniversary party. The entire experience was WONDERFUL!!! Doug was our driver an was very accomodating to ALL the needs of needs of our guests. The trolley arrived on time, actually early to surprise my parents. When we were done with lunch at Navy Pier, we called and he was right there. He was able to surprise my parents with a stop at the church they were married at,along with a drive by of the homes they grew up in. I would recommend them without hesitation. My parents are still talking about this trip! Thanks again for making the day a memorable one. read more

I cannot say enough about the service at Second City Trolley. From start to finish, I was treated nicer and with more professionalism than any other business I have ever encountered. They were unbelievably accommodating to my ever-changing RSVP list that I had for the trolley for my boyfriend's birthday. I did a lot of digging before choosing to go with Second City and I can 100% tell you that they have the absolute best rates in town. The 30 person trolley that I ended up going with was super clean, heated (I figured that "heated" would mean that it would be about 50 degrees in there...not so, it was comfortable for everyone with their coats off on a really cold night), AND they have Ipod connectors on board to jam to. :) The driver was prompt and bent over backwards to make our event the best ever. I will be recommending this place to anyone that will listen! THANK YOU SO MUCH! read more

This company did not give us the greatest experience. We used this company for a trolley on our wedding day. The place of business is not the most professional looking. The first time we tried to meet Thomas and see what the trolleys looked like in person, the person meeting us did not show up. We rescheduled a week later and were able to see the trolleys ok. Bahar is better to work with and gave us more confidence in the company, however this changed completely on our wedding day. We signed a contract with them to originally pick up the bridal party at 2:00pm. We changed the contract over email several months before the wedding to be 1:45 and confirmed this twice, with two different people, over the phone the week of the wedding. Bahar assured me that the trolley would actually get there at 1:30 so that we could load everything on it and be able to leave at 1:45. On our wedding day, the trolley didn't show up until 1:50 and the driver made no apologies. He said the contract time was for 2:00. The driver also didn't have our scheduled routes that we had provided to the company. Thomas had assured us that the driver would have the route that we provided. Thankfully, I had another copy of the route with me so that the driver knew where to go without me telling him the whole way. All in the all, we ended up getting to the church on time (although not as early as we wanted) and the trolley ride after the ceremony was fun and our driver got us around the city fast to take our bridal party pictures at various scenic locations. Things ended up being fine with this company, but I would hesitate to recommend them to anyone. read more

I just rented second city trolley for a barcrawl for my birthday and it was great! I had the smallest group of 25 and actually upgraded a day before to the 30. Of course, some people called sick the day of and I wanted to downgrade back to a 25 person trolley. They said it was too late in the day but since they never mentioned a specific time and rather said "you can call the day of and see" - they honored their word and gave me a discounted price. They have great customer service but it is hard to get someone on the phone on the weekend. Our driver was great and was very prompt on timing picking us up from each location. They provide coolers and garbage bags and the seats are on the perimeters of the trolley rather than all facing forward (huge plus!). Get all the details before upgrading if you're not sure but I would say, our experience was as good as it gets. I would recommend them for any friend renting a trolley in Chicago! read more