If you’ve never been to Chicago then the words skyscraper, backyards, and picnics on the beach shouldn’t all belong in the same sentence. However, you can easily visit all three in on Saturday afternoon. Chicago’s public transportation is also the best in the country. And when we say that we mean the you won’t get hella lost or mugged or sticky after a ride on the bus or train. Its clean (enough), fast, and full of normal people. This city also kills patio season since summer is like Heaven here. Every bar, restaurant, apartment, and open grassy space somehow turn into a Chicago patio from June to August.
Want glam and glitter? Then the Chicago Loop is a breathtaking place right on the river with 5 star restaurants and cocktail lounges. On the other hand you can take a trip to the wild side, or 20 minutes north, and the city completely changes. Beautiful brick town homes, cute cafes, and dogs parks everywhere. Chicago magically changes into a bustling suburb of trendy restaurants and neighborhood bars. If your really feeling adventurous devote some time to the several districts of the city. Hipsterville aka Wicker Park, Foodie Central aka West Loop, or Baseball Hall of Fame aka Wrigglyville are some great starters. Rooftops may require some sneaking up to but the ground floor Chicago patios are plentiful.