10 Most Popular Streets in Chicago

Michigan Avenue is a major thoroughfare that runs north-south through downtown Chicago. Along North Michigan Avenue – between Oak Street and the Chicago River – lies the Magnificent Mile. This 13-block stretch is home to more than 450 retailers and is one of the world's most iconic shopping districts. From luxury boutiques to department stores to multi-storey retail centres, expect an unmatched shopping experience.

The bustling street is worth a stroll even if you aren't a shop-till-you-drop kind of visitor. There are plenty of trendy restaurants, including the 100-storey John Hancock Center. There, you can enjoy fine dining and panoramic views from the rooftop observation deck. Continue south down Michigan Avenue and you can explore the neo-Gothic Tribune Tower, Art Institute of Chicago, Millennium Park, and the Historic Michigan Boulevard District.

Lake Shore Drive is arguably the most visually stimulating street in Chicago. The 15-mile expressway runs alongside Lake Michigan and the bike- and pedestrian-friendly Lakefront Trail. The best way to explore Lake Shore Drive is by driving (or cycling) south to north. You can take in fabulous views of the dramatic skyline and lush parks to one side and the lake’s aqua-hued waters to the other.

Start your drive at Jackson Park, where the Museum of Science and Industry is situated. Head north and stop at Promontory Point to enjoy breathtaking city views. Continuing north, you can visit beaches, spaceship-style Soldier Field stadium, Shedd Aquarium, Field Museum, Navy Pier and Lincoln Park.

State Street is where locals head to enjoy a fun mix of food, shopping, and entertainment. Running north-south, the street anchors the Chicago Loop and the State Street Retail Historic District. The Loop is Chicago’s official downtown area. The vibrant district is packed with historic architecture and incredible dining and shopping scenes.

As a popular shopping destination, you’ll find mega-retailers, trendy stores and local boutiques on State Street. The flagship department store Macy’s is a city landmark. Housed in a National Historic Landmark building, a visit is part-architectural tour and part-retail therapy. Gazing up at the shimmering Tiffany ceiling – the largest Tiffany glass mosaic dome in the US – is worth the visit on its own.

Logan Boulevard is a leafy street in the Logan Square Boulevard National Historic District. You'll find the district in Chicago's Northwest Side, about 7 miles from downtown. The area is home to the most extensive and best-preserved residential streetscapes in Chicago. There are wide boulevards, historic mansions, lush parks, and a vibrant food scene.

Along Logan Boulevard, you can admire a handsome collection of Victorian greystone homes built with Indiana Bedford limestone. There are also brick buildings with Tudor Revival and Prairie School styles. End your stroll at Logan Square. The small, historic plaza hosts the Illinois Centennial Monument. The 65-ft-tall Doric column was erected in 1918 to celebrate Illinois' centennial. You can easily reach Logan Boulevard on the CTA Blue Line.

North Milwaukee Avenue is a diagonal street running through the vibrant Wicker Park neighbourhood in northwest Chicago. Wicker Park is one of Chicago’s hippest and most culturally diverse neighbourhoods, well-known for its buzzing nightlife, dining, and entertainment venues.

At the lively Six Corners, where North, Milwaukee and Damen Avenues intersect, you can browse record and vintage stores and drink coffee at hip cafés. North Milwaukee Avenue also offers access to the 606 landscaped trail. The 2.6-mile stretch of repurposed rail line draws local cyclists, joggers, and walkers.

Clark Street is a jack-of-all-trades road with historic landmarks, local eateries, and nightlife spots. Visitors flock to Clark Street to watch baseball at the iconic Wrigley Field, wander through the 1860 Graceland Cemetery and explore Chicago’s oldest cultural institution, the Chicago History Museum. Live music fans can catch local and national bands at the famous Metro concert hall.

But history, music, and sports aren’t Clark Street’s only attractions. With over 203 bars, Clark Street has the most places to grab a drink in all of Chicago. This means that bar-hoppers can go drinking every night for over 6 months and never visit the same watering hole twice.

If Chicago had to name a dining district, there’s no doubt West Randolph Street in the hip West Loop neighbourhood would be a great start. Locally called “Restaurant Row”, West Randolph Street is lined with some of Chicago’s best eateries and is a foodie mecca. From places presenting upscale tasting menus to 4^th-generation sandwich shops to inventive New American diners, there is a seemingly endless array of great places to eat here.

One block over, you’ll find Fulton Market. The former warehouse district is home to a slew of trendy restaurants and bars. Food aside, West Randolph Street also hosts the year-round Randolph Street Market Festival. The indoor/outdoor market takes place on the last weekend of each month. Shop for vinyl, antiques, jewellery, furniture, vintage clothes, and high-end foodstuffs.

North Wells Street is a busy commercial strip that runs vertically through Chicago’s historic Old Town. The bustling leafy street is lined with Victorian-era buildings now home to a fantastic mix of old-school pubs, charming restaurants, and unique boutiques. For entertainment, North Wells Street is home to the best comedy clubs in Chicago, such as Second City and Zanies Comedy Club. The revered Second City is where Tina Fey, Amy Poehler, Steve Carell, Stephan Colbert, and many other famous comedians started.

Another highlight is the yearly summer Wells Street Art Festival – one of the most prestigious fine art fairs in the United States. Along North Wells Street and other streets in Old Town, you’ll find a treasure trove of creativity, tasty cuisine, live music, and kids’ art activities.

Midway Plaisance is a mile-long boulevard of parkland that links Washington and Jackson Parks in Hyde Park neighbourhood. Locally known as the Midway, the 90-acre linear park features winter gardens, ice skating and in-line skating rinks and multi-purpose fields. Cutting through the University of Chicago, the lush park is a popular spot for students to sunbathe and play frisbee.

On the western end of Midway Plaisance, in Washington Park, stands the epic Fountain of Time. Designed by Lorado Taft, the massive, 124-ft relief sculpture was inspired by Henry Austin Dobson's poem, Paradox of Time. The artwork features Father Time, hooded and carrying a scythe, watching over 100 figures at various stages of life.

Devon Avenue runs east to west on Chicago’s far north side and has a very well-known stretch known as “Little India". Passing through the West Ridge community, it’s an internationally diverse area. With a vibrant mix of authentic Indian, Pakistani, and other South Asian restaurants and shops, plus charming cultural establishments and over a dozen languages in the air, you might forget you’re in Chicago.

Shop windows display statues of Hindu gods and mannequins dressed in shiny, colourful saris. Salons with posters of Bollywood stars offer henna tattoos while Hindi music plays in the background. A few steps away, you can buy halal meat, gold jewellery and stones based on astrology.