Ways to Explore Chicago with Classmates Part 1: Through its Neighborhoods

Ways to Explore Chicago with Classmates Part 1: Through its Neighborhoods

Chicago is very much a city of neighborhoods, with 77 composing the city! These neighborhoods may be more broadly categorized based on their relative orientation to the Loop: Central, North Side, West Side, and South Side (further sub-categorized by near and far i.e. Near North Side). Lake Michigan also borders Chicago to the east, and though it is an excellent place to spend time, I won’t be highlighting it in this post.

A wonderfully communal aspect of Booth is that three quarters or more of the student body lives within a few blocks of the same intersection in Chicago’s business district, called The Loop. The Loop serves as a great, centrally located hub, but an unforeseen joy that has come from my Booth experience has been to explore Chicago alongside my classmates as if it were my first time. Showcasing my city and its offerings to friends of all different backgrounds has been an incredibly rewarding endeavor. There are so many different methods of discovering all that Chicago has to offer, via its restaurants, parks, cultural offerings, etc., but Chicago is undoubtedly a composition of its communities, so they felt like a fitting place to start. That said, feel free to follow my posts to uncover more great ways to explore Chicago alongside your respective companions!

Given our proximity to one another, it would be easy to spend our time solely in The Loop or at classes in Hyde Park. Instead, I encourage my classmates to venture into new neighborhoods; in this post I’ll taking you through some of my favorites. While Chicago has a holistic culture, each neighborhood possesses noticeably different character. I have loved bringing various Boothies to these different neighborhoods, planning a day that involves exploring the innerworkings of each neighborhood and capping a day of adventure with a great dinner at restaurant representative of that part of town. In this post I’ll overview some my favorite hoods, with their position relative to The Loop and a brief description of its feel.


River North

Location: ~0.75 miles north of The Loop (Near North Side)

Descriptors: Commercial, bustling

River North is a bustling part of downtown Chicago (picture high-rises) with many bars and restaurants lining the streets. While demographics are changing, residents are primarily 23–30-year-old singles living their best life in the heart of Chicago. Come here for a good dinner, or venture to Hubbard Street on Friday or Saturday for a lively bar scene with lines spilling out onto the street.

Gold Coast

Location: 2 miles north of The Loop (Near North Side)

Descriptors: Timeless, ritzy

As the name implies, Gold Coast is an older, wealthy neighborhood in Chicago filled with luxury retailers, classic Chicago restaurants, and beautiful, old apartments/homes. Residents primarily include 25-33 year old singles/couples, as well as 45+ year old couples that have owned in the neighborhood for years. Stroll through the fancy shopping districts on Oak and Rush Street, and finish the day in Mariano Park for al fresco dining and a show (people watching).

Lincoln Park

Location: 3 miles north of The Loop (North Side)

Descriptors: Residential, charming

Lincoln Park is a beautiful, more residential area comprised of parks (most notably Lincoln Park), homes/walk-ups, boutique shops, and restaurants. The neighborhood is filled with college graduates, young families, and college students. Lincoln Park is a great destination for brunch, a day in the park, shopping, or an approachable dinner with friends.

To round out the North Side, here are three other neighborhoods worth mentioning:

Old Town: A fun strip of town tucked between Lincoln Park and the Gold Coast – home to bars, restaurants, and the renowned Second City!

Lakeview: A less glamorous version of Lincoln Park to the north of Lincoln Park with no shortage of shops, bars, and restaurants.

Wrigleyville: Home to the one-and-only Chicago Cubs (Wrigley Field), this is a rowdier version of Lakeview with tons of bars and restaurants overflowing with people on game days.


Wicker Park

Location: 2 miles north and 2 miles west of The Loop (West Side)

Descriptors: Hip(ster), trendy

If you venture 20 blocks west of Lincoln Park across the highway you’ll stumble across a very cool pocket of town, Wicker Park. Wicker Park draws a crowd of hip 23-35-year-olds looking for a vibrant part of the city that isn’t as mainstream as the neighborhoods lining the lake. Here, you’ll find boutique shops, thriftier storefronts, and restaurants that have gained notoriety for doing something slightly different. The intersection of Damen & North and the stretch of Division near Damen holds endless opportunities to seek out eclectic storefronts, good eats, and alternative people watching.

Also worth mentioning in the area:

Logan Square: A neighborhood bordering Wicker Park to the north. Slightly more dispersed, but home to must-hit independent bars and restaurants worth travelling to. Avondale is yet another neighborhood branching off of Logan Square with very exciting development.

West Town: A less developed version of Wicker Park on Wicker Park’s southern edge containing hidden gems.

West Loop

Location: 2 miles west of The Loop (West Side)

Descriptors: Hotspot, scene-y

West Loop is a historically industrial part of town that has undergone a dramatic transformation! West Loop may be the new and improved  River North of the 2020s, with fashionable, single 20-30-somethings roaming the streets and seemingly home to the largest number of exceptional bars and restaurants per capita. This is a destination to see and be seen, for top-tier food and drink, or to spend an entire sunny day roaming around the brick streets of Randolph and Fulton Market.



Location: 2 miles south and 2 miles west of The Loop (Near Southwest Side)

Descriptors: Up-and-coming, developing

Pilsen is still very much a work-in-progress, but bursting with rich musical, artistic, and culinary Latino roots, this part of town has become a destination for excellent chefs to open excellent restaurants. Pilsen is worth seeking out for a day at the National Museum of Mexican Art, its canvasing street murals, or a night of cocktails, dinner, and maybe even a concert at Thalia Hall!

Hyde Park

Location: 8 miles south of The Loop (Southwest Side)

Descriptors: Historic, beautiful

No neighborhood guide would be complete without our beautiful, beloved Hyde Park. Come to Hyde Park to see gorgeous, old mansions, charming neighborhood watering holes, and for CLASSES. The University of Chicago campus is truly one of the most breathtaking, thought-provoking, magical places on earth.

While this guide does not do Chicago and its 77 neighborhoods justice, it is a great place to start. Grab a few friends (or don’t) and venture out to one of these neighborhoods for a day. You will find yourself drawn back, loving Chicago more and more for all that its pockets have to offer. The Loop is an extraordinarily cool place but taking classmates/friends out of The Loop to discover different parts of Chicago constitutes the lion’s share of highlights from my Booth experience.  I hope you’ll be a pioneer and come to appreciate it too!

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