City Guide / Chicago

8 Charming Chicago Main Streets to Explore

By Kailey Hansen | Nov 22, 2021
Aerial shot of the Magnificent Mile in Chicago, Illinois.

Whether it’s peak patio season or in the heart of the holidays, Chicago is a fantastic city to explore on foot. If you are new to the area, it can be daunting to know where to begin your adventure. One of the best things about this metropolis is its diverse neighborhoods spanning from the heart of downtown all the way to the suburbs

Many of these areas have charming main streets that are a great starting point for leisurely exploration. These epicenters of shopping, dining, and culture can offer scenic views and a great way to get your steps in! 

See what’s outside the front door of your Landing home, from the Magnificent Mile in Downtown Chicago to the quaint riverside stretch of suburban St. Charles.

1. Michigan Avenue — Downtown Chicago

Perhaps the most well-known shopping corridor of the city is the famous Magnificent Mile, which runs along Michigan Avenue in Downtown Chicago. Deemed the “Mag Mile” by locals, this area features historic architecture such as the Wrigley Building, the Tribune Tower, the Drake Hotel, and more. Once you’ve witnessed these views from ground level, make your way up to the 96th floor of the John Hancock Center (875 North Michigan Avenue) and overlook the Windy City while enjoying a drink at The Signature Lounge (Pro tip: The women’s restroom has absolutely incredible views!). 

Shopping along Michigan Avenue is an experience of its own. The street is home to dozens of big-name stores and the vast Water Tower Place mall for those seeking hard-core retail therapy. Just across the way from Water Tower Place is 900 North Michigan, an upscale shopping center with stores like Gucci and Bloomingdale’s. The Mag Mile is also home to Chicago’s Starbucks Reserve Roastery (one of only six locations in the world!) and offers food ranging from street vendors to high-end dining.

2. State Street — Downtown Chicago

A few blocks over from the Magnificent Mile lies Chicago’s “official” downtown hub, known as The Loop. The Loop offers the quintessential Chicago experience, boasting the city’s theatre district, several arts venues, outdoor parks, and more. If you’re going to choose one street to stroll along within The Loop, it’s State Street, a glorious stretch that will make you feel like you’re in the middle of a movie

State Street is home to the city’s iconic Macy’s location, which includes the lavish Walnut Room restaurant and festive window displays during the holidays. Along this bustling street, you can also find Magnolia Bakery, the Chicago Theater, and the Tik Tok famous Target notable for its gothic-style exterior. Pop into Block 37 for some shopping and entertainment, and then grab a bite to eat at local neighboring favorite, The Dearborn.

3. North Clark Street — Wrigleyville (Chicago, IL)

The Wrigleyville district on the north side of the city is considered a mecca for baseball fans. The centerpiece is Wrigley Field itself, home to the Chicago Cubs, nestled among a residential neighborhood. Whether you enjoy baseball or not, this N. Clark Street area near the field is best known for its homage to sports and its thriving bar scene.

There are dozens of bars in just a mile’s radius, making it the perfect place for a fun night out or to watch the game while grabbing a drink. Visit Slugger’s, a busy sports pub with a dance floor, batting cages, and dueling pianos, or head to Old Crow for live country music and socializing. Spirits aren’t the only thing offered along N. Clark Street. You can reserve a spot at the trendy Happy Camper pizza joint or snag a table across from the field at Big Star and Smoke Daddy.

4. Southport Corridor — Lakeview (Chicago, IL)

Just a short distance from Wrigley Field is a very different atmosphere along the charming Southport Corridor of Lakeview. This destination is accessible most easily ia the Southport Brown Line train stop and is perfect if you want a relaxed stroll that satiates your appetite and hunger for shopping. Visitors can walk up and down Southport Avenue for a beautiful street lined with chic retail and al fresco dining (in the summer).

Complete with an Amazon Books, Lululemon, Anthropologie, and Gap, this is the place to go if you’re looking to shop some big-name brands while enjoying a cozy and homey vibe. Dining options include Crosby’s Kitchen for brunch, Corridor Brewing & Provisions for happy hour, Tuco and Blondie for trendy tacos, or Jeni’s Splendid Ice Cream if you’re feeling a scoop of gooey butter cake ice cream! Southport Corridor is also home to two plant shops, tons of coffee shops, a SoulCycle, and the historic Music Box Theatre.

5. Roscoe Street — Roscoe Village (Chicago, IL)

Nestled amid tree-lined streets and custom-built homes lies Chicago’s tiny “village within the city.” Roscoe Village might only span a few miles, but it’s full of on-the-go families and young professionals. You won’t find high-rises or skyscrapers in this urban neighborhood, but you will find an array of dreamy brunch spots and boutiques that seem straight out of a Hallmark movie. 

Wander along Roscoe Street for a cozy breakfast at John’s Place, or try orange-infused coffee at the eclectic breakfast cafe Orange With A Peel. You won’t want to miss out on a treat from Dip and Sip Donuts, which is only steps away from the whimsical independent bookstore, Roscoe Books. From here, you can peruse local boutiques, Winnie Cooper and Cinnamon, before enjoying Italian fare at Piazza Bella, a glass of wine at Lush Wine & Spirits, or burgers, beer, and trivia at The Reveler and Commonwealth Tavern.

6. Wentworth Avenue – Chinatown (Chicago, IL)

Chicago’s Chinatown, one of the most exciting areas on the city’s south side, is unparalleled in showcasing quality food, art, and culture. Visitors can enter the area’s main strip through the Chinatown Gateway before trying authentic dim sum, bubble tea, noodles, and more along Wentworth Avenue. This entire stretch is filled with delicious eats and includes outdoor artwork that celebrates Chinese and Asian culture. 

Across from Wentworth Avenue is Chinatown Square, a two-story outdoor commercial center featuring live performances and dozens of shops, cafes, and restaurants. It’s not a visit to Chinatown done right without visiting the Joy Yee smoothie window for some of the best fresh fruit smoothies in the city! 

7. Vail Avenue — Arlington Heights, IL

If being away from the bustle of the city is more your speed, Arlington Heights is a suburb located 35 minutes outside Chicago. The area boasts a restaurant scene all of its own inside its vibrant downtown district, decked with string lights and complete with al fresco dining during warmer weather.

Vail Avenue hosts plenty of trendy eateries like Hey, Nonny, a bistro/cocktail bar with live music on the weekends, or the contemporary Cortland’s Garage, best known for its “adult” juice boxes. If a drink is on the menu, come with song requests in mind and visit the Big Shot piano lounge, where a lively pianist serenades modern day tunes.

8. Main Street — St. Charles, IL

The charming suburb of St. Charles, located 40 minutes west of the city, sports a cute and walkable downtown center, renowned for its boutique shopping scene, its riverside dining, and the array of quaint colonial-style buildings. Venture along the aptly named Main Street to find this neighborhood’s character, from the retro candy shop Rocket Fizz, to the historic Arcadia Theatre.

Walkable from Main Street are several coffee shops, bakeries, and even a local indie bookstore. Those looking to grab a drink can stop at Near Alter Brewing Kitchen before enjoying a bite to eat at one of the many restaurants on the Fox River.

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Kailey Hansen

Kailey Hansen is a freelance writer and communications professional based in the land of deep-dish pizza. She has lived in both the city and the suburbs of Chicago and enjoys writing about the amazing things the Windy City has to offer. When she's not dishing about the best places to grab a slice of deep-dish, you can find her writing (and obsessing) about binge-worthy TV shows for BuzzFeed and why cats are the best (and absolutely outlandish creatures) for Rover's blog, The Dog People.