Second City Trolley 312.532.8542 Or E-mail us


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Wedding Trolleys & Special Event Transportation Rentals in Chicago and Suburbs

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 RESERVE THE TROLLEY as early as possible since dates fill up fast 

Trolley Wedding Packages

Second City Trolley Rentals offers Saturday wedding packages. We also offer 20% savings on our Friday and Sunday Wedding Packages. Please click on the links below for further description.

    Additional Fees and Services

    Additional trolley time - for weddings
    Can be purchased after your initial package time. After our 4 hour package, you can purchase 1 hour of service at the rate of $250.00 per hour. After 4 hours of service, more time can be added in ½ hour increments of $125.00 per ½ hour.

    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 starts when we arrive at your initial location.

    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.

    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