The best way to savor Chicago is by foot, but the city's extensive and efficient public transportation system – which carries around 1.5 million passengers a day on subways, buses, and elevated trains (known simply as "the El") – provides easy access between multiple points downtown, outlying neighborhoods, and the suburbs.
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.
Our Experts save you money with travel deals and advice
Always ask for a room upgrade when you arrive at your hotel. They may laugh, but it never hurts to try!
Laura Motta Director, Deals Publishing
Sign up for the Top 25 Newsletter
to get exclusive weekly deals