Though often defined by its skyline, the heart and soul of Chicago lives in its many vibrant neighborhoods. Here—outside the downtown Loop—is where the incredible diversity of the city is most evident. Globe-trot through ethnic eateries, marvel at magnificent churches or browse boutiques filled with homemade trinkets. With 77 communities each brimming with their own unique cultures, Chicago has a lot to explore.
From the built environment of the South Loop and Gold Coast neighborhoods to the green spaces in Lincoln Park and Jackson Park, you can easily feel like you are traveling between different cities altogether. Not sure where to begin? Let these highlights inspire your itinerary:
Arts & Culture
Chicago is most certainly a theater town with over 250 professional companies throughout the city, including five Regional Tony Award winners. Lincoln Park is home to two: Steppenwolf and Victory Gardens. From one type of stage to another, live clubs of all shapes and sizes dot the music landscape, from the Aragon Ballroom, Riviera Theater and Green Mill Jazz Club in Uptown to Schuba's Tavern, Metro and The Vic in Lakeview. Seek out neighborhood museums such as Swedish American Museum in Andersonville and National Hellenic Museum in Greektown, or immerse yourself in art at gallery districts within the West Loop, River North, Bridgeport or Pilsen.
Architectural & Historical Sights
Any architecture buff will tell you that Chicago is home to more than the skyscraper. From the classic South Shore bungalows, Frank Lloyd Wright designs in Beverly and Hyde Park, and the Victorian mansions and simple brick cottages throughout Old Town, Wicker Park and Lincoln Park, these homes create a distinct sense of place and community. For more looks into the past, don't miss the Alfred Caldwell Lily Pool in Lincoln Park, step into beautiful old churches like St. Stanislaus Kostka in Noble Square, check out the Union Stock Yard Gate in Back of the Yards, or cruise down the historic boulevard system through Logan Square and beyond.
Chicago is one of the world's culinary epicenters so make sure to bring an appetite. Enjoy award-winning fine dining (consider North Pond and Boka in Lincoln Park, Goosefoot in Lincoln Square or Arun's in Albany Park) or go traditional with Chicago-style hot dogs, pizza and Italian beef sandwiches (there's a go-to spot in just about every neighborhood), from Portillo's in River North to Al's Beef in Little Italy. For a taste of Chicago's ethnic flavors, surround yourself in food and culture in Chinatown and Greektown, or seek out the gems in the Mexican-American community of Pilsen, the Puerto Rican community of Humboldt Park and the incredibly diverse Devon Avenue of West Ridge, where Jewish, Middle Eastern and Southeast Asian cuisines offer an international blend.
- Nightlife & Entertainment
For a night on the town, head to one of the many wine bars, cocktail lounges, sports taverns or dance clubs. The Wrigleyville area in Lakeview is always bustling, whether there's a baseball game or not, as is nearby Boystown. The main intersection of North, Milwaukee and Damen Avenues in Wicker Park is filled with trendy, destination hotspots, while Lincoln Park draws a young, casual crowd. For some laughs, the North Side neighborhoods have a mix of comedy clubs, including Zanies and the famed Second City in Old Town.
Neighborhood finds are a mix of bargain deals and luxury splurges. Charming, tree-lined Lincoln Park lines its chic streets like Armitage, Halsted and Webster with independent boutiques. The latest fashions, accessories, home décor, cosmetics and gifts can be found here, as well as Southport Corridor in Lakeview. Shop Wicker Park and Bucktown and stay on trend with the latest looks from local designers, browse styles from upscale retailers (think Marc Jacobs and Joe's Jeans) or stay in a budget at the many vintage and resale shops. Or uncover the best in interior design, art and antiques in Andersonville, Edgewater, West Town and Roscoe Village.
To make your adventure even easier, consider a tour with the Chicago History Museum or Chicago Architecture Foundation. The city's distinct communities come alive on neighborhood tours, revealing rich histories and celebrated cultural traditions, local landmarks and unseen treasures. Affordable and convenient, these outings (travel by motorcoach, bicycle or foot) offer fully-planned itineraries and an expert local guide to lead the way.
Looking for a welcoming face to help you on your way? Get around Chicago with free, guided walks led by people who know it best – local Chicagoans. A fun, friendly and informative way to get the inside scoop on where to go and what to see, Chicago Greeter is a free, year-round service that pairs small groups up to six people with a volunteer based on the neighborhood and interests of choice (for example, Pilsen public art or family-friendly Lincoln Park), as well as language spoken.
Get more details and sign up at chicagogreeter.com.