Hold Your Horses
A horse-drawn carriage ride around the Magnficent Mile is about as romantic as they come. Make sure to bundle up and bring along a blanket to snuggle under with your Valentine. The Noble Horse Carriage Rides are a fun way to tour the North Michigan Avenue shopping district. Boarding and Drop off is at Michigan Avenue and Chicago Avenue (800 North). Pick up and Drop off service to/from a nearby hotel/restaurant is available for an extra fee.
Romantic Dinner at White Castle????
Yep, seriously. Cloth table cloths, candle light, the whole works. Check your local White Castle since its only available at certain locations. And book early! They fill up fast.
Jazz it Up
Chicago has a proud history of jazz and blues music, and there are multiple venues that offer live music several days a week. One of the most famous and popular is the Green Mill jazz club, located in Andersonville, about 20 minutes north of the Loop at 4802 N. Broadway. If your valentine loves jazz, this is a great place to take them.
The Brew Bus
If you and your honey enjoy craft brews, a Chicago Beer Tour will have you saying "Cheers" in no time. Two tours are scheduled on Saturdays and both are geared toward craft beer lovers and beer drinkers. The noon one starts at Goose Island Brewing Company, one of Chicago's oldest craft brewing companies while the 4pm one begins at Haymarket Brewing. With each of the tours guests will enjoy between four to six samples at each location (included in the ticket price) and learn more about the craft beer scene in Chicago.