Chicago Labor Day Guide 2010

The sprawling rooftop patio atop this West Town biker bar--it welcomes everyone, even those not in chaps--is a prime spot to bid adieu to Chicago?s outdoor drinking season. Kick back at an umbrella-topped table while you drown your end-of-summer sorrows with Jim Beam, which flows from taps, or revel in the conclusion of teeny bikini season by scarfing a gloriously gluttonous Fat Boy Burger.

All weekend long, the Windy City commemorates its jazzy roots at the free 32nd annual Chicago Jazz Festival. This year, for the first time, the party will expand to three separate locations (Millennium Park, the Chicago Cultural Center and Grant Park) for a celebration of good tunes belted out by a mix of local and national talent. We can?t wait to check out Chicago legend Ramsey Lewis?s 75th birthday bash/concert on Friday at the Jay Pritzker Pavilion.

This probably isn't ?the year? for the Cubs, but while the considerably more promising White Sox are on the road (facing their red Boston counterparts), the Northsiders will attempt to open September on a high note. They?ll start by welcoming the Mets to the Friendly Confines for a weekend series, and then host the Astros for another three-game run, which kicks off Monday. Although the playoffs seem out of reach, the last ballpark dogs and soft pretzels of the season are well within striking distance.

We love fresh air and good food just as much as the next guy, but can?t resist the drool-worthy deals at this shopping mecca just west of the city. Packing away those summer duds won?t be so depressing when you get to replace them with a new stock of cable-knit sweaters from J. Crew and that all-important pair of fall boots from Aldo or Kenneth Cole.