When you ascend the stairs at the Chicago Blue Line stop, the first thing you see is the Osco looming over the intersection of Chicago and Milwaukee. This is a neighborhood that is still developing a personality. Sandwiched between West Town and River West, the area is home to several art galleries and small theaters, as well as plenty of brand-new, yuppie-fied condos. There are plenty of dining options to be found, but bars and clubs are sparse. Consequently, the area tends to clear out after dark.
Panhandler rating: There aren't really enough people around to attract panhandlers.
Safety rating: While the neighborhood isn't dangerous, it's relatively deserted after dark.
Place to be seen solo
Windy City Cafe
Anyone who has waited for an hour and a half in a crowd of hipsters at Toast will appreciate the simplicity and straightforwardness of Windy City Cafe. Serving breakfast and lunch from 7 a.m. to 5 p.m. (8 a.m.-4 p.m. on weekends), Windy City Cafe is a typical diner but better: well lit and clean, with friendly service and bottomless cups of coffee. Just about everything on the menu costs less than $7, and you can even take your food to go. Breakfast is served all day, with a full complement of omelets, skillet and pancake options. The menu also includes sandwiches and other entrees for the non-breakfast crowd. The diner's two rooms effectively separate the smokers from the non-smokers, a unique asset for those who wrinkle their nose at the mingling aromas of pancake syrup and smoke.
No wallet needed
Intuit's bright green entryway and retro glass block windows give little hint as to the contents within. Intuit bills itself as "The Center for Intuitive and Outsider Art." Dedicated to showcasing the talents of artists who have had little influence from mainstream art, dubbed "outsider art," the gallery operates as a leading national nonprofit organization with more than 600 members. The organization has two gallery spaces in its headquarters on Milwaukee. The front gallery hosts a series of temporary exhibits, while the Study Gallery in back is home to the permanent collection and longer-running exhibits. Exhibits include works by un-trained painters, sculptors and folk artists. Quilts, carvings and crayon drawings here show levels of beauty and thoughtfulness that propel them into the realm of art. Admission to the gallery is free, and it is open Monday through Saturday from noon until 5 p.m. Occasional lectures and panel discussions take place throughout the year.
D'Agostino's River West
As far as Italian food goes, D'Agostino's offers the no-frill basics. For cheap food, conveniently located right in front of the Chicago Blue Line stop, you can't go wrong here. The bright dining room is clean, whether you sit at the bar or at one of the tables, where you can take your pick from a predictable menu of pizza, pasta and sandwiches, most costing less than $10. Beer specials attract diners looking for an economical meal with an inexpensive drink to wash it down. Slightly smaller than D'Agostino's Wrigleyville location, the Ogden offshoot doesn't have as much character as its sister on Addison, but it's more family, less frat. The outdoor tables offer a relaxing area to kick back and enjoy a beer in the fresh air. While you're out there, be sure to wave to the hipsters across the street on the sidewalk at Matchbox: They're probably paying twice as much for their drinks.
Dining Room at Kendall
Tomorrow's best chefs have to learn their trade somewhere, and The Dining Room at Kendall is that place. Operated by Kendall College's School of Culinary Arts, The Dining Room offers five-star quality at two-star prices. When you're eating the homework of one of the country's premier culinary programs, you can be sure that the food won't disappoint. The menu changes quarterly, with dinner entrees ranging from $15-$20 and lunch from $10-$15. The Dining Room is BYOB, so bring your favorite bottle of wine (and pony up a $5 corkage fee). Leave the Boon's Farm at home, though: The vibe here is sophisticated, providing a gorgeous view of the Chicago skyline, romantic lighting and amazing food. The Dining Room's hours are limited, so reservations are recommended.
The Dining Room recently introduced its Monday Night Dining Series, a five-course, prix-fixe feast prepared by successful alumni. The $38 price includes non-alcoholic beverages, tax and tip. All tips go to the school's scholarship fund, so philanthropic diners may want to leave a little extra.
Chicago Tribune Freedom Center
So you have relatives coming in from out of town and you can't stomach another trip to Navy Pier? Take them to the Chicago Tribune Freedom Center, located just west of the Loop. This massive building is home to the Chicago Tribune's printing and distribution operations, as well as the regional distribution center for the New York Times. Free tours of the facility are available on weekdays, but you have to call ahead to reserve your spot. This is a factory, so dress accordingly, and don't bring children younger 10 ten years old. The one-hour tour covers all aspects of production, from the trainloads of raw paper delivered each morning to printing, packaging and distribution.
For the artiste
Chicago Center for the Performing Arts
The Chicago Center for the Performing Arts hosts a variety of original productions and well-known theater classics at its 350-seat main stage. Ticket prices are typical for a theater of this size, starting at about $40 per ticket. The shows here vary widely, allowing you to catch burlesque shows and sentimental dramas. Past performances include the "Rocky Horror Show" (starring Jerry Springer and Mancow Mueller), as well as "Miracle on 34th Street" and "Singin' in the Rain." The theater also hosts special events throughout the year, such as a two-night run of "Wigfield," starring Amy Sedaris, Paul Dinello and Stephen Colbert, and a two-night flamenco show starring Novisimo, a group of up-and-coming flamenco artists. The Chicago Center for the Performing Arts is also home to the Players Workshop (an improvisational arts program) and the Chicago Center School of Music, which offers private instruction, classes and workshops for all ages. A 200-seat playhouse, two cabarets, a restaurant, and an outdoor plaza are in the works for the future.