It’s time again for Travel Twister. This week we’re heading to Chicago. Now spin the wheel, using the color-themed el (never “elevated”) stops as your guide. It’s all happy landings.

Right Hand, Blue Line
Artsy types, rejoice: Wicker Park, the city’s coolest hood, is all young hipsters and thrift, while nearby Bucktown’s got BabyBjörns and boutiques.

Damen Avenue: Start with a breakfast burrito at Earwax (1561 N. Milwaukee Ave.; 773-772-4019), then hit P.45 (1643 N. Damen Ave.; 773-862-4523) for emerging designers. Looking for vintage? The best is at Lenny and Me (1463 N. Milwaukee Ave.; 773-489-5576). Pop over to Pontiac Cafe (1531 N. Damen Ave.; 773-252-7767) for a beer before making new friends over Frisbee or a pickup soccer game at Wicker Park (N. Damen & N. Wicker Park Aves.). When you’re exhausted, crash at Ray’s Bucktown B&B (2144 N. Leavitt St.; 773-384-3245).

Division Street: Toodle around on a scooter rented from Windy City Vespa (773-276-5200; now closed). It’s time to fuel up at Milk & Honey Cafe (1920 W. Division St.; 773-395-9434) and stock up on indie designers at Habit (1951 W. Division St.; 773-342-0093; now closed).

Right Foot, Red Line
Addison Street: Around here, baseball’s not a sport, it’s a religion. Root, root, root for the Cubbies at Wrigley (1060 W. Addison St.; 773-404-2827). After they win (curse? What curse?), drain the adrenaline at a show at Metro (3730 N. Clark St.; 773-549-0203).

Chicago Avenue: The Gold Coast is the ritzy shopping stretch along the Mag Mile. And The James (55 E. Ontario St.; 877-526-3755), with its lounge, J Bar, and spa, is a vacation in itself. Equally awesome: Park Hyatt (800 N. Michigan Ave.; 312-335-1234).

Left Hand, Brown Line
Sedgwick Street: Old Town is charming, inviting, and, um, old. Live it at the Old Town Chicago B&B (1442 N. North Park Ave.; 312-440-9268). Feeling funny? The Second City (1616 N. Wells St.; 312-664-4032) was once home to Bill Murray and Tina Fey. You’ll laugh so hard you’ll lose all bladderly functions.

And, finally, you can’t visit Chicago without rollin’ down the river.

Clark/Lake Streets: Mies, Frank, and Louis left their (blue) prints all over. The best views are from a Shoreline Architecture Cruise (312-222-9328).

State/Lake Streets: After many years and billions of Benjamins, Millennium Park (N. Michigan Ave. & E. Randolph St.) opened with gardens, the Gehry-designed amphitheater, and the Park Grill (11 N. Michigan Ave.; 312-521-7275). Pick up a picnic at Fox & Obel (401 E. Illinois St.; 312-410-7301), then head to the park for free summer concerts.

Yeah. It’s your kind of town.

Want more Windy City? Check out DailyCandy Chicago.