You'll have no trouble feeling romantic during a Chicago Horse & Carriage ride.
Cinderella may not be real, but her tale of happily-ever-after -- which has forever romanticized glass slippers, handsome princes and horse-drawn carriages -- can be. Here are my suggestions for recreating a magical night, with or without a fairy-tale budget.
RICH MAN: Take a customized tour of the city with Chicago Horse & Carriage, which picks up passengers on Michigan Avenue at Pearson Street. It can be an open or enclosed carriage and goes anywhere you'd like, from Michigan Avenue to Navy Pier to a two-hour ride through Lincoln Park. Rides run $40 for 30 minutes, $60 for 45 minutes, or $80 per hour, and customized routes (ride by your work, favorite bar or "special spot") for five dollars more.The group accommodates special requests, but just make sure it is not during rush hour (4-6 p.m. Monday-Friday) and the weather is above 15 and below 90 degrees.
Also try Antique Coach and Carriage, which offers rides for $40 per half hour or $80 per hour. Have a nice dinner downtown and have that carriage pick you up for a rolling view of the city lights afterward.
POOR MAN: No money, pumpkins or mice? Pick up a two-wheeled alternative to a city tour date. The Chicago Bikeposition 2010 season started in March, offering architectural bike tours of different city neighborhoods during one weekend afternoon per month. Learn all about Chicago's famed architecture...for FREE! This month's tour, set for May 23, is of Humboldt Park.