Chicago Labor Day Planner

1603 N Lake Shore Dr, Chicago, IL 60614 (map)

If the objective is to hold onto summer, then a ship-shaped bar that's literally on the beach seems an appropriate place to while away a few hours during the holiday weekend. The drinks might be ridiculously expensive, but drinking in your swimsuit has its price, people.

1650 Premium Outlets Blvd, Aurora, IL 60502 (map)

We love fresh air and good food, but we also plan to spend our holiday weekend taking advantage of the sales, and the deals should be drool-worthy at this shopping mecca just west of the city. Face fall stocked up on cable-knit sweaters from the J. Crew Outlet and that perfect pair of fall boots from Aldo or Kenneth Cole.

337 E Randolph, Chicago, IL 60602 (map)

The Windy City celebrates its jazz roots at the free 31st annual Chicago Jazz Festival all weekend long. Three stages will be set up around the Petrillo Music Shell (at Jackson and Columbus). Our pick: be-bop era tenor sax legend Von Freeman jamming on Sunday afternoon on the Jazz on Jackson stage.

1600 N 25 E, Chesterton, IN 46304 (map)

Where's the best beach in Chicago? Oddly enough, it's in Northwest Indiana. For an incredibly doable end-of-summer getaway, hop on the South Shore Line at the Millennium Park station, and in under an hour you'll disembark 50 miles southeast, and just a few minutes' walk from the park entrance. There's a wide swath of beach, hiking trails and campgrounds and, for the less outdoorsy, plenty of cute B&Bs nearby.

5491 S South Shore Dr, Chicago, IL 60615 (map)

This prime lakeside picnic spot on a rocky, wooded outcropping is Hyde Park's sweet little secret. It isn't as overrun as the lakefront to the north, and there's an unobstructed view of downtown. Pack your own picnic or stop by Morry's Deli at 55th and Cornell and order enough triple-decker sandwiches for the whole crew.