1. Visit Millennium Park and walk over to the Art Institute after spending time in the park. The Art Institute connects to the park....World Class.
2. Visit the Museum Campus and pick between the Field Museum of Natural History, Adler Planetarium, Shedd Aquarium----or visit all 3. While at the Museum Campus you will see spectacular views of the city skyline looking back across Lake Michigan.
3. Visit Navy Pier....
4. Take a tour of Wrigley field if the Cubs are out of town.
5. Catch a Cubs game if the Cubs are in town.
6. Visit the Chicago Botanical Gardens which are north of the City.
7. Visit the B'Hai temple which is north of the City.
8. Shop on Michigan Ave. and visit Nordstrom, Water Tower Place, Macys and get some Chocalate at the Hershey store... (Also visit the American Girl Store).
9. Get a drink on the 96th floor of the Hancock building observatory. The lounge is one floor above the observatory and you avoid paying the observatory fee. Most Chicagoans agree the Hancock building offers superior views over the Sears/Willis tower. You can see across Lake Michigan (60 miles away directly is Warren Dines state park) on a clear day.
10. Chicago Pizza is a tourist thing... Get a real Chicago Italian Beef at Al's on Taylor. For desert, Marios Italian ice (south side tradition) is accross the street from Als.
11. Sunbathe and/or swim at Oak St beach (or any of the other 20 beaches in Chicago).
12. East at Chef Rick Bayless restaurants---such as XOCO or Frontera grill.
13. Catch live theatre or an orchestra in the theater district.
14. Attend an outdoor music concert at Ravinia. There is a train station in the middle of the outdoor theater and is quite unique.
15. Go to Six Flags which is north of the city.
16. Go to Rivers Casino near O'Hare and have dinner before/afterward at Gibsons steakhouse.
17. take hubby and have tea at the Waldorf in their tea room (State St.)
18. Take hubby and have lunch and tea at the Walnut room at the old Marshall Fields (now Macys) on State St.
19. Visit the Sculptures in Daley Plaza and walk accross the street to the modern "state of illinois" building---widely regarded as the defacto state capitol of illinois. This building is where the previous two Illinois Governors schemed and defrauded Illinois citizens resulting in both currently incarcerated at the same time.
20. Windella Boat ride on the Chicago River and/or Lake Michigan.
21, Have a "cheeseboooorga cheeseboorga" at the famous Billy goat tavern located directly below the Wrigley building on a hidden st. (lower wacker dr.) which is underneath Michigan ave. Billy Goat was made famous in Saturday Night Live and John Belushi.
22. Experience muti-cultural diversity in 2 hours by riding the "L" 'red/purple Line" train from the affluent Wilmette to the economically challenged terminus at 87th st.
23. Visit the Free Lincoln Park Zoo ----also visit the many sculptures and other park amenities.
24. Catch a concert at "the double door" in Wicker Park... Many music careers were lanuched there----most famously "the Smashing Pumpkins".
25. Many free concerts and festivals occur at Grant Park which is south of Millenium Park. these include "taste of Chicago" and "Gospel Fest".
26. Check out Buckingham fountain in Grant Park.
27. Ride a bike along Chicagos 26 mile lakefront path. If you get tired, you can catch the "L" or a bus and bring your bike on with you.