Skip the observatory and head to the 96th-floor bar on the 95th floor—you'll spend your money on an exorbitantly priced cocktail instead of the entrance fee and enjoy the same view. Read more.
For deep-dish pizza, stop into any of the eight Lou Malnati’s locations in the city or Pequod’s Pizza in Lincoln Park; for a classic Chicago-style hot dog, try Portillo’s downtown. Read more.