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! .

We offer the most special trolley experience in the Chicago area. Bridal Parties and Bar Hopping parties both love our beautiful custom interiors! Brides love our classic styling and antique couches, while Pub Crawlers enjoy our friendly, professional drivers and open seating that encourages greater socializing. All of the guests on our trolleys enjoy the atmosphere created by our iPod stereo hookups, fully air conditioned and heated vehicles, some trolleys with open decks and balconies giving you the best views of our beautiful city and skyline.We have the trolleys with the most character and soul!

The Wedding Day
Travel to the chapel in style aboard an elegantly styled wedding trolley adding a unique charm to your special day. The trolley evokes a bygone era while providing reliable group transportation. The entire bridal party can ride together making your arrival to the chapel, photos and reception even more memorable. The trolley is perfect for candid wedding group pictures. You may have family and friends arriving from all over the state, or even the country, many of these people may be unfamiliar with the area; so let us be your designated driver, helping your family and friends get to the wedding ceremony and back safely to the hotel after the reception.

Our wedding parties appreciate the festive atmosphere, which the trolley brings to the wedding and thoughtful personalities of our drivers. Our drivers will assist the bridal party and guests. Your wedding day is important to us. Second City Trolley rentals will be happy to assist you with all your wedding transportation needs. So, plan ahead, call for rates and remember to gate io english as early as possible since dates fill up fast., Please be advised that booking via phone constitutes as a signed contract  

Trolley Wedding Packages

Second City Trolley Rentals offers Saturday wedding packages. Wedding Packages. Please click on the links below for further description.

Additional Fees and Services

Additional trolley time
Can be purchased after your initial package time. Overtime will be prorated hourly at the regular rate

Location Fee
The location fee is based on the distance the trolley has to travel between our base of operations, Chicago, and the most distant location of your event (and our return to Chicago). Not all locations have a fee. The fee covers our traveling costs and surcharges. The price does vary depending upon the location of your event. Your clock yelp4ts when we arrive at your initial location.

click to Book St. Patrick's Day TROLLEY

Guarantee and Confirm Date
NON-REFUNDABLE Deposit to Reserve Vehicle: 30% or $260 (whichever is greater) reservation deposit on a Master Card, Visa or American Express will guarantee your wedding date. Summer dates sell out fast. Plan ahead and reserve your white Rolls Royce or trolley for your wedding day.

Gratuity for Driver


It is appreciative and customary, the day of event, to pay the driver a gratuity if you are pleased with their services.
Wedding Trolley Features Depending on the size of the passenger, seating is not guaranteed for everyone. Mostly encountered with 40 passenger Trolleys
• 25 to 40 Passenger capacity with perimeter seating
• Speaker Sound System with Ready RCA cable for your Smartphone
• Air-conditioned and heated for your comfort
• Perimeter seating for more intimacy
• Totally enclosed to keep out any unwanted weather