Wicker Park & Bucktown Best all-rounder
Near Northwest · $$Why it made the list: The city's coolest walkable stretch, vintage shops, indie boutiques, record stores, great coffee and some of Chicago's best restaurants and bars, all radiating from the six-corner intersection of Milwaukee, North and Damen. It's the easy first neighborhood to fall for.
Logan Square Food & drink
Northwest · $$Why it made the list: A little further out and more local, a leafy square, boulevards of greystones, and one of the best restaurant-and-bar scenes in the city without the crowds. It's where Chicagoans go to eat and drink well, from the famous Lula Cafe to a deep bench of cocktail bars.
Pilsen The murals
Lower West Side · $Why it made the list: The heart of Mexican Chicago and the city's most vivid neighborhood for street art, block after block of murals along 16th Street and 18th Street, superb taquerias and bakeries, galleries, and the excellent (and free) National Museum of Mexican Art.
Lincoln Park Classic Chicago
North Side · $$$Why it made the list: The polished, leafy North Side classic, handsome brownstones, the lakefront, and a genuinely free world-class zoo, plus the shops and restaurants of Armitage and Halsted. It's the pretty, walkable, easygoing Chicago that people picture when they picture living here.
Andersonville Local favorite
Far North Side · $$Why it made the list: The quietest gem on the list, a historically Swedish, now proudly independent and LGBTQ-friendly neighborhood built around a single walkable stretch of Clark Street, lined with independent bookshops, boutiques, bakeries and restaurants. No chains, no crowds, just a lovely afternoon.
⭐ Bonus Pick: Hyde Park
For a different side of the city, head to the South Side's Hyde Park, the University of Chicago's Gothic campus, the excellent (free) Robie House neighborhood of Frank Lloyd Wright architecture, the Obama connection, and the Museum of Science and Industry nearby. It's a longer trip but a rewarding, un-touristy half-day.
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