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Chicago’s Neighborhoods Not to Miss

By Nicole Schnitzler

Apr 15, 2020

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Lincoln Park is a favorite for its parks, boutiques, and brownstones.

Photo by Jon Bilous/Shutterstock

Lincoln Park is a favorite for its parks, boutiques, and brownstones.

When in the Windy City, make time for shopping in Lincoln Park, biking through Wicker Park, dining in the West Loop, and more.

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Chicago is a city built on diverse neighborhoods. Each of its 77 community areas brings something different to the table, helping make the Windy City such a exciting place to visit. 

Still, the sheer number of neighborhoods can be intimidating to travelers. Should you spend time on the North Side or the South Side? Lincoln Square or Logan Square? And which is better, Lincoln Park or Wicker Park?

To help, we’ve rounded up five of our favorite neighborhoods to explore for every kind of fun, from boutique shopping and bike riding to sipping craft cocktails and savoring some of the city’s most delicious fare. 

Lincoln Park

Known for its massive namesake park, picturesque brownstones, and blocks of boutique shopping, Lincoln Park is one of Chicago’s premier neighborhoods. Start your day here with coffee and rustic French pastries at Floriole café, then pop next door for a cupcake (or two) at Sweet Mandy B’s—one of the city’s most beloved bakeries. Next, visit the Armitage-Halsted district for hours of shopping at some of the city’s most sought-after boutiques and artisanal food shops. Art Effect is a one-stop shop for hand-crafted jewelry, women’s clothing, bath products, and whimsical gifts, while spots like Vosges Chocolate, Jeni’s Ice Cream, and Berco’s Popcorn are full of delicious treats.

For a proper lunch, head to Blue Door Farm Stand, a bright and airy space for seasonal American cuisine. Afterward, make your way to Lincoln Park Zoo—one of the few free zoos in the country—stopping on the way to stroll DePaul’s campus or check out the Wizard of Oz sculptures in aptly named Oz Park. Come dinnertime, make it a date at any one of the neighborhood’s best restaurants, namely Range (for farm-to-table fare), Centre Street Kitchen (for modern, global flavors), or, for a real splurge, North Pond, a fine-dining fixture in a historic building in the heart of Lincoln Park proper.

Lincoln Square

Head to leafy Lincoln Square for independent bookstores, tasty bakeries, and more.

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Situated about seven miles north of downtown Chicago, Lincoln Square is one of the city’s most welcoming neighborhoods—a reputation strengthened over the years by its strong Greek, Eastern European, and Mexican communities. Quirky, small businesses are one of the area’s biggest draws. Take, for example, Merz Apothecary, a drugstore opened in 1875 that specializes in herbal medicines and formulas, or the Book Cellar, an independent bookstore that hosts a variety of community-driven events and author talks throughout the year. 

There’s no shortage of sustenance here, either. Visit Café Selmarie for treats from pastry chef Kyleen Atonson, a Chopped Sweets winner who’s known for her whimsical takes on dessert. More cookies are available at Dorothy’s Can-Do Bakery and Café, where all proceeds benefit Gateway to Learning, a training center serving those with developmental disabilities. With dessert down, work backward to dinner at Gather, a favorite for its New American food and craft cocktails. Rather than grabbing a table, snag a seat at the restaurant’s Kitchen Counter to watch the chefs craft winning plates like Korean barbecue carrots, cacio e pepe, and braised short rib with herbed mashed potatoes. 

Bucktown and Wicker Park

Wicker Park draws a hip crowd with great shopping and a groundbreaking cocktail bar.

Full of popular restaurants, bars, and music venues, the adjacent neighborhoods of Bucktown and Wicker Park draw some of the city’s coolest clientele. They’re also a favorite of growing families, thanks to quiet streets, impressive shopping, and the 606, a 2.7-mile recreational trail and park built on former railroad tracks. Kick off your visit with a workout at Spynergy, a recently opened cycling studio in the heart of Wicker Park, or grab some wheels from Chicago’s Divvy bike share program and hit the 606. 

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Post-sweat, do brunch at neighborhood gem Mable’s Table or at Hot Chocolate, where chef Mindy Segal serves a menu of decadent day starters (think pot roast hash and brioche french toast) and, of course, a righteous hot chocolate selection. Afterward, skip the mainstream stores on Damen Avenue and hit the boutiques on Milwaukee instead—don’t miss Myopic Books and hip outfitter Una Mae’s. Come happy hour, head to the Violet Hour, a clandestine bar where a seasoned, suspender-clad team has been leading the Chicago cocktail scene since 2007. And when hunger strikes, try the locally driven fare at Café Robeywhich sits in a stylish boutique hotel from Mexico City–based Grupo Habita. 

West Loop

The West Loop owes its reputation as a culinary mecca to restaurants like Blackbird.

Once the world’s busiest meatpacking district, the West Loop now lays claim to Restaurant Row, a vibrant strip that’s lined with some of Chicago’s best places to eat. Though Blackbird and Avec were among the first spots to land here, it was Girl and the Goat—the debut restaurant from Top Chef winner Stephanie Izard—that helped catapult the area to culinary fame in 2010. 

Enjoy lunch at Bar Siena or Bad Hunter before an afternoon of games and karaoke at Punch Bowl Social or shopping at upscale stores like Billy Reid and M2057 by Maria Pinto. Once dinnertime rolls around, hit a classic on Restaurant Row or try one of several other elevated dining options: greenhouse-driven Eden, Danish-inspired Elske, Michelin-starred Smyth, or maybe Argentinean staple El Che Steakhouse & Bar. The West Loop also features several of Chicago’s coolest hotels, including Soho House, the Ace, and the Hoxton, so you might want to consider basing your stay here.

Logan Square

Don’t miss the international restaurants in Logan Square, like the Macanese Portuguese Fat Rice.

With its long boulevards, tree-lined blocks, and charming squares (including its namesake), Logan Square has long served as a landing pad for Chicago’s immigrant community, especially those from Mexico, Poland, Cuba, and Puerto Rico. Nowadays, the neighborhood is also one of the city’s more prominent culture hubs, with concert halls, cafés, and restaurants galore. 

In 1999, chef Jason Hammel and his team established Logan Square as a dining destination with the opening of Lula Cafe, a corner fixture with seasonal Midwest fare and a wildly popular brunch. Since then, numerous restaurants have followed suit, serving food from all over the world. Try Fat Rice for Macanese Portuguese plates, Papa Cenar for Spanish tapas, Daisies for flavor-packed pastas, and Parson’s for some serious fried chicken. When it comes to drinks, don’t miss Billy Sunday (a favorite for vintage spirits) and gin haven Scofflaw (where you’ll want to be at midnight, when the bartenders bring out freshly baked cookies). The next morning, cure your hangover with coffee from Gaslight or Estereo.

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>>Next: Plan Your Trip With AFAR’s Travel Guide to Chicago

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