To those who think the Midwest is bereft of culture and nightlife, Chicago is the ultimate rebuttal. No, we're not all beer and bratwurst, though every city has its vices. From the architectural marvel that is downtown to countless tight-knit ethnic neighborhoods, Chicago proves on every corner that it's a city that works--very well, in fact. 

COOL PLACES
Buddy Guy's Legends 
A big-league blues club worthy of its guitar-wailin' owner's name.
El: Red Line to Harrison
754 S Wabash Ave, Chicago, IL
(312) 427-0333

Lincoln Park
A five-mile-long backyard for three million people, with room and outdoor activities to spare.
Bus: 22, 36 to Fullerton Pkwy; 76, 77, 151, 152, 156 to park
Chicago, IL
(312) 742-7726

Navy Pier
This tourist-packed peninsula extends for more than a half-mile into the swells of Lake Michigan.
Bus: 29, 56, 65, 66 to Navy Pier
600 E Grand Ave, Chicago, IL
(312) 595-7437

North Michigan Avenue
Chicago's version of Fifth Avenue.
El: Red Line to Chicago or Grand
Chicago, IL


The Magnificent Mile - Michigan Avenue		 Price Assurance Math (180x150)

Sears Tower and Skydeck
Get a bird's-eye view of the city--on a clear day you can see 80 miles in any direction.
El: Orange or Brown Line to Quincy
233 S Wacker Dr, Chicago, IL
(312) 875-9696 

  • The View: The Sears Tower stands 1,454 feet tall, 110 floors high. On a clear day, viewers can see four states. Don't get dizzy--the average sway is 6 inches from the center. A new Guest Relations Team adds a nice touch and often goes out of its way to be helpful and informative.

  • The Extras: After a $4 million renovation, the Sears Tower Skydeck boasts more than the view. On the way to the top, you can watch TV. When you get there, a new multimedia Chicago exhibit gives you more to do than just look out the windows. Murals and interactive special effects wrap around the entire floor, highlighting Chicago history, writers, artists, historic landmarks, memorable events and sports teams. 

John Hancock Center
All grace and strength, it's shorter than the Sears Tower, but it's still among the world's 10 tallest buildings. El: Red Line to Chicago; bus: 3 to Chicago Ave/Michigan Ave; 66 to Michigan Ave; 145, 146, 151 to Delaware Pl.
875 N Michigan Ave, Chicago, IL
(312) 751-3680

  • The View: The third tallest building in Chicago, the Hancock stands 1,127 feet tall, 100 floors high. The Hancock's greatest draw is the option of kicking back in the 96th floor Signature Lounge with a beer or cocktail and taking in a lakeside view of the city. Add the killer location on North Michigan Avenue, and you have the Chicago insider's favorite sky-high pastime.

  • The Background: Designed by Skidmore, Owings & Merrill, the same prominent Chicago firm that designed the Sears Tower, the Hancock--"Big John," as it was nicknamed--was completed in 1970 after five years of construction. It can withstand winds up to 132 miles per hour. 

Wrigley Field
Known as the Friendly Confines, this classic ballpark is a monument to the national pastime.
El: Red Line to Addison
1060 W Addison St, Chicago, IL
(773) 404-2827

Frank Lloyd Wright Home and Studio 
Take a walk through the residence of Chicago's famous, groundbreaking architect.
951 Chicago Ave, Oak Park, IL
(708) 848-1976

Chicago Lakefront Path
One of Chicago's crown jewels, offering stunning views of Lake Michigan and the city skyline.
Chicago, IL 


Chicago's Buckingham Fountain

Buckingham Fountain
This Grant Park attraction is the perfect spot for a romantic stroll.
Grant Park, Chicago, IL
(312) 747-2633

WHERE TO EAT

Billy Goat Tavern
A true Chicago classic, this bar/lunch counter was immortalized on SNL for its "cheezborger, cheezborger, cheezborger."
El: Red Line to Grand; bus: 3, 145, 146, 147, 151, 157 to Tribune Tower; 29, 65 to Lower Michigan Ave
430 N Michigan Ave, Chicago, IL
(312) 222-1525

Charlie Trotter's
Simply put, one of the world's finest restaurants.
El stop: Brown line to Armitage
816 W Armitage Ave, Chicago, IL
(773) 248-6228


Chicago as seen from Sears Tower Skydeck		 Green Car (155x155)

Gino's East
Graffiti-covered walls and to-die-for deep dish make odd-but-definitely-welcome bedfellows at this pizzeria.
El stop: Brown Line Chicago or Red Line Grand
Multiple locations, Chicago, IL
(312) 943-1124

Harry Caray's Restaurant
Nostalgic Italian restaurant proudly carries on the legacy of the dearly departed Cub announcer.
El: Red Line to Grand
33 W Kinzie St, Chicago, IL
(312) 828-0966

Portillo's Hot Dogs
A comfy setting, great dogs, superlative Italian beef ... this is Chicago food done right.
El: Red Line to Grand
100 W Ontario St, Chicago, IL
(312) 587-8910

QUICK PICK RESTAURANTS

312 Chicago 
136 N La Salle St, Chicago, IL
(312) 696-2420
"Top private dining room in Chicago - Forbes Magazine" 

Catch 35 Seafood Restaurant 
35 W Wacker Dr, Chicago, IL
(312) 346-3500
"It doesn't get any fresher than this - Sun Times." 


Chicago as seen from John Hancock Building

Nine Steak House 
440 W Randolph St, Chicago, IL
(312) 277-0207
"Style with substance, flashy yet straightforward. ''' Chic. Tribune" 

Chief O'Neill's 
3471 North Elston, Chicago, IL
(773) 583-3066
"Check out our Halloween Bash" 

Thyme 
464 N Halsted St, Chicago, IL
(866) 276-7306
"Chicago's premier outdoor dining w/ live jazz on Tuesdays & Sundays." 

MK 
868 N Franklin St, Chicago, IL
(312) 482-9179
"Thank Goodness It's Fall Come See What We're Cooking!" 

Sopranos 
2901 N Sheffield Ave, Chicago, IL
(773) 871-0990
"Featuring Live Music Thurs, Fri & Sat Nights & Full Martini Menu" 

Francesca's Fiore 
7407 W Madison St, Forest Park, Il
(708) 771-3063
"Audience choice best Italian." 

Gino's East 
Multiple locations, Chicago, IL
(312) 943-1124
"One of Chicago's best pizzas" 

Edwardo's Natural Pizza 
1212 N Dearborn St, Chicago, IL
(312) 337-4490
"Award Winning Stuffed Pizza" 


One of Chicago's downtown beaches		 Price Assurance Math (180x150)

Molive` 
107 E Delaware Pl, Chicago, IL
(312) 573-6300
"An American bistro--enjoy our year-round atrium cafe." 

Rushmore 
1023 W Lake St, Chicago, IL
(312) 421-8845
""A hidden gem on W. Lake St." - Chi. Social" 

Kevin 
9 W Hubbard St, Chicago, IL
(312) 595-0055
"Top Newcomer/Rated (Top by Cuisine-Zagat survey 28 rating)" 

Pizzeria Ora 
545 N LaSalle, Chicago, IL
(312) 464-1872
"Known for our deep-dish! Dine-in, carry out & quick delivery." 

Benihana Japanese Steakhouse & Sushi Bar 
166 E Superior St, Chicago, IL
(312) 664-9643
"An experience at every table." 

Mar y Sol 
816 W Randolph St, Chicago, IL
(312) 563-1763
"Randolph Street's hot new restaurant, stylish cocktails & dining." 

Sushi Wabi 
842 W Randolph, Chicago, IL
(312) 563-1224
"Voted "Best Sushi in Chicago" by Chicago Tribune readers." 

Sushi Doraku 
1139 N State St, Chicago, IL
(312) 867-7772
"Chicago's hottest sushi restaurant." 

Dragonfly Mandarin 
1206 N State Pkwy, Chicago, IL
(312) 787-7600
"Come for our food, stay all night. Enjoy Tienchu Nieh master dishes" 

ARTS AND SIGHTS

Art Institute of Chicago
Beyond the famous feline sentinels flanking this museum's steps resides one of the world's great art collections.
El: Red Line to Monroe; Blue Line to Monroe; Green, Orange or Brown Line to Adams/Wabash
111 S Michigan Ave, Chicago, IL
(312) 443-3600


The Chicago River - Marina City Apartments on Right

Museum of Science and Industry
This hands-on behemoth is the antithesis of those boring "Look, but don't touch" museums.
Bus: 1, 6 to Hyde Park Blvd; 10, 55 to museum
5700 S Lake Shore Dr, Chicago, IL
(773) 684-1414

Second City
This club's clever sketch and improv material put Chicago comedy on the map.
El: Brown Line to Sedgwick; bus: 11 to La Salle St/North Ave; 22, 36 to North Ave; 72 to Wells St; 156 to North Ave
1616 N Wells St, Chicago, IL
(312) 664-4032

Steppenwolf Theatre Company 
This giant of Chicago theater is a supporter of daring new works.
El: Red Line to North/Clybourn
1650 N Halsted St, Chicago, IL
(312) 335-1650

Chicago Blues Festival
Chicago is understandably proud of the world's biggest free outdoor festival. 
@ Grant Park, El: Red Line to Monroe; Green, Orange or Brown Line to Madison/Wabash or Adams/Wabash, Chicago, IL
Free

Taste of Chicago
Chicago's hallmark festival, the Taste, isn't only about chowing down, it's also about getting down. 
@ Grant Park, El: Red Line to Monroe; Green, Orange or Brown Line to Madison/Wabash or Adams/Wabash, Chicago, IL


Chicago River - Sun Times & IBM Plaza on right		 Green Car (155x155)

Chicago Air and Water Show
Air and water travel are redefined by the amazing speed and grace of world-class performances. 
@ North Avenue Beach, Bus: 72 to Lake Shore Drive; 22, 36 151, 156, to North Avenue, Chicago, IL

Chicago International Film Festival
Close to 100 films from dozens of countries play each year at the country's oldest competitive international film fest. Festival is held for two weeks at the beginning of October 
@ Landmark Century Centre Cinema, El: Brown Line to Diversey; bus: 22 to Broadway/Diversey Pkwy; 36 to Clark St/Diversey Pkwy; 76 to Broadway/Clark St, Chicago, IL

 

Price Assurance Check (728x90)