Fine Dining

• Chicago is a culinary epicenter that is well respected for casual as well as fine dining options. While more family-friendly options such as Chicago-style pizza or may be Chicago's best-known foods, The Windy City also offers myriad fine-dining options. Alinea, for example, offers some of the most inventive and well-executed menus in the country. The restaurant's tasting menu changes daily; make reservations a month in advance.
  
  

Second City

• Second City is Chicago's world-renowned comedy and live theater improv venue. It has produced some of the country's most well-known stand-up comedians, as well as serving as a stopping point for many internationally touring comedy artists. You can book shows at Second City through its online ticket service. Reserving a private table for two gives you a chance to have some privacy while watching some of the world's best-known comedians.
  
  

Horse-Drawn Carriage Ride

• Located at the corner of Michigan and Chicago avenues, the Chicago Horse and Carriage company offers horse-drawn carriage rides throughout Downtown Chicago, as well as through Millenium Park. Take a tour in the open air and see Chicago's famous architectural landmarks, or choose a more secluded route that takes you through the nooks and crannies of Chicago's largest public park. You have the option of adding a dozen roses or a stuffed plush animal to your carriage ride. Book the ride for sunset for an especially romantic touch.
  
  

Jazz Concert

• Chicago has a longstanding jazz music scene, with many of the most important jazz artists of the past century coming from the city. Chicago is also a major stop on many international tours, so you have the chance to see some of the best jazz artists in the world performing live there. Reserve a private table at either the Green Mill Cocktail Lounge or the Jazz Showcase, and let the smooth and romantic sounds of Chicago jazz carry you away.