The Loop/West LoopChicago’s geographical core bustles with suits and shoppers by day and theater fanatics by night. Go further west to give your stomach a workout at some of the trendiest restaurants in town.
The Magnificent Mile/River North/StreetervilleBoatloads of tourists arrive by the thousands to shop at the same stores they have back at home, before checking out the gallery, club and restaurant scene that rages in River North.
The Gold Coast/Old TownFace-lifted ladies parade their pooches past the most prestigious addresses on the North Side while frat boys and the trixies who love them look to score big at the bars on Division Street.
Lincoln ParkOld Chicagoans cling to their million dollar brownstones while young republicans and DePaul students invade the perfectly manicured streets of Armitage Avenue’s Victorian-lined shopping district.
LakeviewTake yourself out to the ballgame in Cubs-centric Wrigleyville, sip oversized martinis with a drag queen in gay-oriented Boystown, or push a double-stroller in family-friendly Roscoe Village.
Wicker Park/BucktownThese sibling neighborhoods personify urban cool. Perfect your hipster stance at one of the clubs or live music venues on scrappy Milwaukee Avenue or give your Visa a workout at the charming boutiques lining Damen.
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See if your airline allows for extended layovers so that you can include an additional destination in your trip without booking separate flights.
Laura Motta Director, Deals Publishing
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