Founder Dick Portillo began serving his delicious Chicago-style hot dogs out of a trailer back in 1963, and now this legendary franchise has nearly four dozen locations (including one in Buena Park, California). The busy River North diner sports a 30's gangster theme and has counters for different items, including hot dogs, sandwiches, salads and desserts. Portillo's musts include the classic hot dog, topped with mustard, relish, onions, tomatoes, pickles and sport peppers, as well as the Italian beef sandwich, served on French bread. Celebrate this calorie splurge with a piece of their homemade, fudge-topped chocolate cake.
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