With steely skyscrapers, lakefront beaches and world-class museums, Chicago will blow you away with its low-key yet highly cultured awesomeness.
The city center is an architectural wonder, but it’s Chicago’s mural-splashed neighborhoods – full of inventive restaurants, fringe theaters and sociable dive bars – that will create lasting memories of your time in the Windy City.
Here are the best neighborhoods to explore on your trip to Chicago.
Best neighborhood for sightseeing
The Loop is Chicago's center of action, named for the elevated train tracks that encircle its busy streets. And though there’s debate on whether the Loop is an actual neighborhood, no one can deny it’s the beating heart of the city.
There's lots to see in the Loop: the Art Institute, Willis Tower, the Theater District and Millennium Park are the top draws among the skyscrapers, while the city's biggest festivals keep people flocking to the area's large green spaces.
The Loop holds loads of lodgings. Cool boutique and architectural hotels are the specialty. The neighborhood is convenient to the parks, festival grounds, museums and the Theater District, with easy transport access to anywhere in the city.
But the Loop does get a bit dull after dark because most restaurants and bars are geared towards office workers. There's not much open after 9pm.
Streeterville and Navy Pier
Best neighborhood for shopping
Streeterville packs in deep-dish pizza parlors, buzzy bistros, art galleries and so many upscale stores that its main vein – Michigan Avenue – has been dubbed the "Magnificent Mile."
This neighborhood is unapologetically, in-your-face commercial. Shops, restaurants and amusements abound. Navy Pier, a half-mile-long wharf of tour boats, carnival rides and a flashy, king-sized Ferris wheel, is the neighborhood's top sight.
Architecture is a neighborhood highlight, thanks to iconic buildings such as the Tribune Tower and Marina City. Art is another strong suit of the area, especially underrated sights such as the Driehaus Museum and Arts Club of Chicago, as well as Streeterville's many galleries.
The Near North is Chicago's most lodging-packed neighborhood, with hotels on practically every street corner. They're mostly midrange chain properties, though a couple of nifty boutique hotels and hostel-hotel hybrids are mixed in.
This neighborhood is also where you'll find Chicago's mother lode of restaurants. There's a huge variety, from deep-dish pizza to ritzy seafood to modern Mexican. It's a touristy area, thanks to all the hotels that are here, so prices can be higher than they need to be.
Best neighborhood for luxury
The Gold Coast has been home to the wealthiest Chicagoans for well over a century. Stylish locals glide in and out of the neighborhood's top-end boutiques as the occasional Tesla or Rolls-Royce wheels along the leafy streets.
Lodging options in the chi-chi Gold Coast area tend to be large, luxury hotels, which offer easy access to both downtown and the lakefront, plus you have a shopping bonanza at your doorstep.
The Gold Coast is the epicenter of hot-spot steakhouses, swanky eateries and martini lounges for pretty people on the prowl. Glamorous old-time lounges and skyscraper bars with spectacular views can also be found in this neighborhood.
Lincoln Park and Old Town
Best neighborhood for comedy and live music
The green space of Lincoln Park is Chicago's premier playground, filled with lagoons, walking paths, beaches and zoo animals. Lincoln Park, the surrounding neighborhood, adds top-notch restaurants, kicky shops and lively blues and rock clubs to the mix.
To the south, stylish Old Town hangs on to its free-spirited, bohemian past with artsy bars and the improv-comedy bastion Second City.
Lodgings in this area range from hotels to B&Bs and hostels, and they have lots of character. They're near fun nightlife, and some are a short walk to Lincoln Park, the zoo and beaches. They're a bit removed from downtown's sights, however. It's also a popular neighborhood for apartment rentals.
Old Town's options are quieter and quainter. This is a great area to catch some top-notch live performances in the evenings, with numerous options ranging from blues and rock music to comedy improv and dramatic plays.
Best neighborhoods for museums
The South Loop offers a wide range of things to do. The Field Museum, Shedd Aquarium and Adler Planetarium cluster at the lakefront Museum Campus. Peaceful 12th Street Beach and hilly Northerly Island offer nearby refuges to ditch the crowds. Historic house museums and a famed blues sight beckon nearby. This neighborhood doesn't have many hotel options besides what's around the enormous convention center.
Pilsen and Chinatown
Best neighborhood for culture
Meanwhile, at the neighborhood's southern edge, Chinatown bustles with noodle shops and small storefronts. Further west is Pilsen, where Mexican culture mixes with Chicago's bohemian underground, and colorful murals, taquerias and cafes result.
Pilsen's 18th Street teems with Mexican taquerias, tamale shops, hip gastropubs and modern American restaurants. Caminos is a neighborhood staple. On the weekend the dive bar hosts Los Naturales, a pop-up natural wine bar, before transforming into a late-night hot spot.
Blue Island Avenue is a similarly rich vein. Chinatown offers a densely packed smorgasbord of noodle houses, low-cost bakeries and dim sum places.
Pilsen has activist cafes, microbrewery taprooms and artsy dive bars, while the Near South Side has neighborhood pubs and leafy patios. Chinatown isn't much of a drinking destination, though it rocks for satisfying late-night, post-booze munchies.
Lakeview and Wrigleyville
Best neighborhood for nightlife
Lakeview is the overarching name of this good-time neighborhood, known for its nonstop lineup of bars, theaters, rock halls and global eateries. Wrigleyville is the pocket that surrounds star attraction Wrigley Field, where big changes are afoot.
For years, sticky-floored boozers were the stock in trade. Now cocktail bars, fancy donut shops and trendy eateries have joined the game. Foodies and families are thrilled. Those who perceive a loss of local color are not.
Nightlife is the specialty of Lakeview and Wrigleyville, and there are heaps of options: traditional sports bars and new cocktail bars around Wrigley Field, dance clubs and gay bars in Boystown and cozy wine bars, English pubs and jazz-wafting little taverns scattered elsewhere throughout the neighborhood.
Some great new boutique hotels have popped up recently, especially near Wrigley Field. They join several already-existing boutique properties and B&Bs, most of which are surrounded by rollicking bars, restaurants and music clubs. The main areas can be congested and rowdy at night. Room prices typically rise when the Cubs are playing.
Wicker Park, Bucktown and Ukrainian Village
Best neighborhood for restaurants
The three neighborhoods of Wicker Park, Bucktown and Ukrainian Village in the larger area of West Town are trendy, hot property. Hip record stores, thrift shops and cocktail lounges have shot up, though vintage Eastern European dive bars linger on many side-street corners.
Wicker Park is the more commercial heart; it's flanked by Bucktown, Ukrainian Village and East Village, and smaller Noble Square. The restaurant scene includes a number of top Michelin-starred/James Beard Award nominees. Chef Bill Kim’s UrbanBelly, Big Star, Dove’s Luncheonette are among the neighborhoods’ stand-outs.
The art galleries, onion-domed churches, a couple of national/ethnic museums and writer Nelson Algren's house keep the area interesting. Walking or cycling the 606 trail is an excellent way to spend an afternoon.
For hostels, B&Bs and apartment rentals away from the tourist masses, this is your neighborhood. Everything is near buzzy nightlife and trendy shops, plus it's only a 15-minute L ride to get downtown.
Trendy restaurants like Wazwan open almost every day, with many serving nouveau takes on classic comfort food. Division Street is a bountiful vein of snazzy bistros and pubs, many of which have sidewalk seating.
Milwaukee, Damen, Division and Chicago Avenues burst with cocktail lounges and chic bars, while authentically retro mom-and-pop joints thrive quietly on the neighborhood's side streets.
Unsurprisingly for such a hip area, the northwestern neighborhoods have a bevy of choices for an evening's entertainment. You'll find venues for indie rock, hip-hop and other popular genres, as well as a few of Chicago's smaller independent theater companies.
West Loop and Near West Side
Best neighborhood for trendy Chicago
The West Loop buzzes with hot-chef restaurants and on-trend bars that have taken over former meatpacking factories.
There’s chef Joe Flamm’s Rose Mary combining Croatian and Italian fare, Swift & Sons steakhouse, Chikatana and La Josie for Mexican. Get over to Blind Barber for a drink and late night dancing. Development continues big time, with condos, tech-company offices and brand-name hotels rising at a dizzying pace.
The West Loop packs in a group of the city's hippest, most trend-setting properties, with prime access to all the surrounding fashionable eats. You'll pay big for the pleasure.
Fancy cocktails are West Loop's calling card. Distilleries, wine bars and coffee shops that take their lattes seriously add to the scene. Further flung in the Near West Side's industrial landscape is a smattering of breweries.