The windy city is a cornucopia of modern art, fine dining, cutting edge comedy, and die-hard sports fans. Snap a photo of your reflection in the silver Cloud Gate sculpture at Millennium Park before heading to Grant Park to get hit with the refreshing spray of Buckingham Fountain. There are dozens of museums and theater companies in Chicago, so a cultural experience is never hard to find. You’re sure to laugh your head off at the Second City Theater, the professional launch pad of many famous comedians.

Located on the shores of Lake Michigan, Milwaukee is perhaps best known for its famous breweries and the Major League Brewers, but there's more to the city than beer and baseball. Milwaukee is rich in historical and cultural attractions, making it the perfect place for a weekend of exploring. Check out the newly expanded Milwaukee Art Museum or the Mitchell Park Horticultural Society, which hosts an annual show of the same flora and fauna seen in Georgia O'Keefe's paintings. Those interested in the city's history can visit the grand Pabst Mansion, former home of one of the city's famous beer barons, or the Milwaukee Public Museum, to see what life was like in Old Milwaukee. If the kids are along, don't miss the Milwaukee County Zoo or the Betty Brinn Children's Museum. Of course a trip to the "Genuine American City" would not be complete without a tour of the Miller Brewing Company and a Brewers game at Miller Park.

Any city that can be the butt of a Simpson's joke ("That's it! We're all going back to Winnipeg!") and simultaneously one of the most vibrant cultural centers in Canada is tops in our book. The city's history of isolation and self-sufficiency means that Winnipeggers are unpretentious and sincere (and fun-loving enough to name Homer an honorary citizen). Though the winters are long and cold, there are plenty of indoor activities to both keep you warm and stimulate your imagination.