Castaways Bar & GrillChicago | Website
Located on the upstairs level of a boathouse on North Avenue Beach, this bar and grill is something you'd expect to find on MTV spring break -- especially due to all the bikini-clad coeds sauntering around on hot, sunny days. Affectionately known to locals as “Casty’s, the downstairs concession stands serve hot dogs, hamburgers and ice cream, but the rooftop is a full-service bar and restaurant. Check out the Beachcomber Salad, with lettuce, chickpeas, black olives, tomatoes and grilled chicken or the Roast Beef Philly Griller with thin slices of beef, swiss cheese, green peppers and onions with chipotle mayo. On the drink menu is a full line-up of beer and wine, along with signature beachy cocktails like mai tais, jungle juice and the Bermuda Triangle (Vodka, pineapple juice and blue curacao). Weekends feature live music, including rock, retro and contemporary bands. And it should come as no surprise that beachwear is welcome.