10 Coolest Neighbourhoods to Explore in Chicago

Chicago is home to some of the world’s most famous skyscrapers, sports teams and American culinary delights. It’s also a city with some really cool neighbourhoods. Here's my list of the 10 coolest neighbourhoods in Chicago worth taking the time out to explore.

1 Lincoln Park

Photo credit: Matt Bigelow

Lincoln Park is one of those neighbourhoods that can seem like a quiet, residential area one minute, and a bustling, vibrant one the next. Armitage Avenue is lined with upscale stores, while Clark Street has cafés, restaurants and sweet shops. If you’re there at night, make your way to Lincoln Avenue which is full of bars and pubs packed with students, skaters and more. Two places worth visiting are Branko’s Sandwich (1118 West Fullerton Avenue), which does a mean meatball sandwich, and Kingston Mines (2548 North Halsted Street), one of the city’s best-known blues clubs.

2 Chinatown


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Visiting Chinatown in any American city is as much a part of the experience as visiting its main sights. Chicago’s Asian epicentre is home to 65,000 Chinese residents, making it one of the largest neighbourhoods of its kind in the United States. The main drag here is Wentworth Avenue where you’ll stumble upon restaurants, distinctive shopping and the Chinatown Gate.

3 Boystown

Photo credit: nathanmac87

Chicago’s aptly named Boystown is one of the largest lesbian, gay, bisexual and transgender communities in the United States. It was also the first officially recognised gay neighbourhood in America. Primarily a commercial area, the main arteries are Broadway and Halsted St, the latter of which has over 30 different gay and lesbian bars, restaurants and nightclubs.

4 Wicker Park / Bucktown

Photo credit: John Zacherle

If ‘hipsterville’ is the type of place that you like to hang out in, then these adjoining neighbourhoods are the places to go when in Chicago. The streets are packed with art galleries, boutiques, bookstores and vintage clothes shops. If you’re going after dark, hunt down Big Star (1531 N Damen) in Wicker Park which does great Mexican food and Debonair Social Club (1575 N Milwaukee Avenue) in Bucktown which is something of a ‘concept bar’.

5 The Loop

file Photo courtesy of Daniel Schwen.

While there is more than one distinctive area to Chicago’s downtown neighbourhood, collectively it is known as ‘The Loop’. Named after a streetcar that circled the area back in 1882, The Loop is where you’ll find landmarks like the Magnificent Mile, the Willis Tower (formerly Sears) and the John Hancock Centre.

6 Wrigleyville

file Photo courtesy of Ron Cogswell.

If you end up in Wrigleyville it will probably be for the following reason – you’ll be going to see the Chicago Cubs in Wrigley Field, the second oldest baseball stadium in the world. As a result, Wrigleyville it’s great for nightlife (whether you’re going to a game or not). Trot up and down Clark, Addison and Sheffield Avenues and you’ll be able to take your pick from countless bars, Red Ivy (3255 N Clark St) being one of the liveliest.

7 Roscoe Village

file Photo courtesy of vxla.

When you see the ‘Village Within the City’ sign in this quiet pocket of the city, you know the pace of life is going to be somewhat slower than the rest of Chicago. It is…quite significantly in fact. The thoroughfare at the heart of it all is Roscoe Street from Damen to Western Avenue, but explore the area around it and you’ll many more cafés, specialist store and more.

8 River North

file Photo courtesy of Howard Cheng.

Located just north of Chicago’s celebrated Magnificent Mile, River North is where locals want to go to unwind at night that little bit out of the downtown area. The result is a string of bars on W Division St, and N Clark St. Many of these have wow factor, Moe’s Cantina (155 W Kinzie St) and Y (224 W Ontario St) being two such venues.

9 Logan Square

file Photo courtesy of Tony Webster.

Logan Square is similar to the Wicker Park / Bucktown area in that it’s very hipster-centric. The main difference is that here, it’s a little bit rougher around the edges. There are more dive bars, more skater kids, more tattoos and, overall, more of an edge. It’s great for the budget, with lots of places for cheap eats and drinks, two in particular being Café Bella (3311 W Fullerton Ave) and Boiler Room (2211 N California Ave).

10 Hyde Park

Photo credit: Luiz Gadelha Jr.

If history and culture are your things, then Hyde Park should be at the top of your itinerary for Chicago. Here you’ll find the home of Barack Obama, the University of Chicago and the Museum of Science and Industry – the largest science museum in the Western Hemisphere.

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