(according to Citysearch)

1.Wrigley Field
1060 W Addison, Chicago, IL
Sip an Old Style and cheer on the Cubbies from the lively bleacher seats of this historic ballpark.

2.Art Institute of Chicago
111 S Michigan Ave, Chicago, IL
Spend an afternoon at this famed Michigan Avenue museum and gaze at Seurat's "Sunday on La Grande Jatte."

3.Signature Lounge
875 N Michigan Ave, Chicago, IL
Settle into a window-side table 96 stories above the Magnificent Mile and drink in spectacular city views and sidecars.

4.Lou Malnati's Pizzeria
439 N Wells St, Chicago, IL
Go to deep-dish heaven with a flaky-crusted, cheese-oozing pie from this pizza joint. FT thread on Chicago Pizza here: http://flyertalk.com/forum/showthread.php?t=308700

5.Buddy Guy's Legends
754 S Wabash Ave, Chicago, IL
Catch an authentic Chicago blues set by the club's guitar-wailin' owner during his annual stand each January.

6.The Wiener's Circle
2622 N Clark St, Chicago, IL
Get yelled at by the feisty late-night crew while ordering a Chicago dog at this legendary spot for red hots. FT thread on Best Chicago Hot Dog here: http://flyertalk.com/forum/showthread.php?t=334192

7.Second City
1616 North Wells St., Chicago, IL
Glimpse tomorrow's comedy superstars at the legendary club that helped launch Bill Murray, Mike Myers and many other famous jokesters. FT thread on Second City here: http://flyertalk.com/forum/showthread.php?t=334101

8.Chicago from the Lake
435 E Illinois St, Chicago, IL
Take an architectural riverboat tour and find out who built the corncob-shaped Marina Towers.

9.Billy Goat Tavern
430 N Michigan Ave, Chicago, IL
Dig into a double cheeseburger with chips (no fries!) at this divey lunch counter made famous by John Belushi on SNL.

10.Drake Hotel
140 East Walton Pl, Chicago, IL
Take a break from Mag Mile shopping with afternoon tea at this world-famous hotel.

“Bonus Items”

Gino's East
633 N Wells St, Chicago, IL
Graffiti-covered walls and to-die-for deep dish draw crowds of families and tourists to this classic pizzeria.


The Palmer House Hilton
17 E Monroe St, Chicago, IL
This classic Loop hotel has 19th-century charm and 21st-century service and amenities.

Whitehall Hotel
105 E Delaware Pl, Chicago, IL
This deceptively large boutique hotel is popular with visiting celebrities who like their privacy.

The Talbott Hotel
20 E Delaware Pl, Chicago, IL
A quaint, quiet British ambience on a pleasant, tree-lined street.

Mr. Beef
666 N Orleans St, Chicago, IL
A celebrity favorite, the Italian beef sandwich at this no-nonsense joint is out of this world. FT thread on best Italian Beef in Chicago here: http://flyertalk.com/forum/showthread.php?t=308703

(according to Citysearch)