1. Walk the Magnificent Mile
Michigan Avenue also popularly known as the Magnificent Mile features one skyscrapers after another. There is no better place to experience Chicago than walking along the Magnificent Mile.
2. Make a friend with an Illinois resident
If you are traveling with a local, take advantage of their zip code and save some money. "Time Out Chicago" has information for free Museum days on their site.
3. Millenium Park
Enjoy watching your reflection in the Cloud Gate Sculpture, also known as "The Bean".
4. Explore Lincoln Park
1200 acres of prime lakeshore real estate devoted to recreation and nature, are ponds, a conservatory, public art, statues, bike trails, and a zoo.
5. Eating like a Local
Chicagoans' enjoy eating deep-dish pizza and Chicago-style hotdogs. Portillo's a good place to start for hotdogs. As for pizza, Giordano's and Pizzeria Uno are easily accessible while downtown. It's not free but affordable.
6. Browse the Chicago Cultural Center
Right across the Street from Millenium Park is the Chicago Cultural Center. The building was once the city's library and memorial to the Grand Army of the Republic.
7. Grab drinks in the Signature Lounge
The John Hancock Tower is where you can find the Signature Lounge. Grab a drink and enjoy the free view.
8. La Salle Street
The oldest high rise building in Chicago was built in 1888 by the famous architect duo Daniel Burham and John Wellborn Root. They don't build them like this anymore.