Are you considering moving to Chicago? Or are you simply the kind of traveler that likes to explore the city through the lens of a local? Either way, welcome to our compressed Chicago neighborhood guide (for the Northside) for our one and only Chi-Town.

Chicago is comprised of 77+ neighborhoods that have been woven together to complete the city.  The plus sign is in regards to neighborhoods that have been disputed over the years as to whether or not they can truly be called a neighborhood since they are not recognized in city zoning, but everyone knows what and where they are.  This patchwork of areas has been quilted together to create a diverse cityscape.  What might even be more impressive than the city itself is that each neighborhood has built and maintained a unique identity. 

Chicago’s Neighborhoods & What Makes Each One Unique

The Loop

The truth is that we simply can’t start anywhere else than Chicago’s most historic neighborhood.  Situated just south of the main branch of the Chicago River, this neighborhood is home to some of the most famous spots the city has to offer!  No trip to Chicago would be complete without spending at least an afternoon strolling through this historic section of the Concrete Jungle to view some of the masterful feats of architecture.  Below are some of our favorite buildings to check out while you’re out exploring:

  • Chicago Theater – built in 1921.
  • Marshall Field and Company Building (now Macy’s) – built in 1893
  • The Lyric Opera House – built in 1954
  • The Auditorium Theater -built in 1889
  • The Carbide and Carbon Building – built in 1929


Although the architecture here is some of the city’s most famous, it is also home to the Grant Park complex.  Inside Grant Park, you will find both Maggie Daley Park, and most importantly Millennium Park, home of The Bean!  Millennium Park was completed in 2004 and is filled with scenic art installations good for the whole family.  Cloud gate, or as you probably know it, The Bean is the masterful centerpiece of this urban park mecca.  

If you’re interested in exploring more of the majesty of the Loop and learning about one of Chicago’s oldest neighborhoods, then we would recommend joining us on one of our tours that traverses through the area!  Our Family Food & Bike Tour, our Chicago Favorites Food Walking Tour, or our Holiday Hike: Food Walking Tour are great choices. 

the marquee of the Chicago theater located in the Loop neighborhood of Chicago

Bobby's Bike Hike tour stop at cloud gate art installation, also known as the bean, in millenium park in Chicago

street view of the front of beautiufl buildings on the magnificent mile in chicago

The Magnificent Mile

Ah yes!  The Majesty of the Most Marvelous Magnificent Mile!  Which isn’t actually a neighborhood but rather a district inside of the Streeterville neighborhood.  The Magnificent Mile’s origin story starts after World War II when a man named Arthur Rubloff decided to buy up the real estate along Michigan Street in order to create an upscale shopping destination.  With the help of his business partners, they coined the area the Magnificent Mile.  The idea here was that good old-fashioned word-of-mouth marketing!  If people heard the area was magnificent, then maybe they would be willing to come and check it out.  If they did come to take a stroll down the manicured street, they just might do some shopping while they’re there.  This tactic worked like a wonder and the reputation of the area speaks for itself.

Going shopping at stores like Burberry, Nike, and Sephora, just to name a few, is the obvious pastime of the Mag Mile.  There are, however, a few other things to consider while you’re in the area.  The Chicago Tribune Tower, built in 1923, is one of the most unique structures in the city.  The neo-gothic architecture design is complimented with stones from all over the world.  Trail your fingers over ruins from Cambodia’s Angkor Wat, or stone used to build the Great Pyramids of Giza!  There are around 150 different stone fragments that have been embedded into the exterior of this monument to the creativity and expertise of the human imagination. 

While on your stroll, we highly recommend checking out the Starbucks Roastery.  It is the largest Starbucks in the world and on top of its famous cup of joe, you can take home coffee beans, souvenirs, or just simply enjoy a cocktail at their in-house bar.


The official neighborhood of the Mag Mile is known as Streeterville.  This area is the home to other fan favorites like The John Hancock Building (currently named 875 N Michigan Ave), The Water Tower Place, and even Navy Pier!  Consider grabbing a Chicago Classic Deep-Dish Pizza at Gino’s East while you’re in the area.  Their location in Streeterville, close to the Mag Mile, is famous for the graffiti visitors have left on the walls since the restaurant’s inception.

The Gold Coast

As we journey up North, we now come across The Gold Coast, a neighborhood famous for its mansions, and Gibson’s Bar and Steak House!  Here in the Gold Coast, you can grab a scrumptious breakfast at the Original Pancake House, and then walk north on State Street to view mansions such as the Original Playboy Mansion, the mansion rented by Dwayne Wade of the Miami Heat, or even the historic mansion owned by the Catholic Church.  

If you’d like to learn more about this area and view these mansions with the help of a tour guide, then we would recommend taking Bobby’s Bike Hike Neighborhoods Bike Tour or our signature Bike’s Bite’s and Brew’s tour.

Old Town 

The next neighborhood is a subsection of Lincoln Park, but this is where the comedy magic happens! No trip to Chicago is complete without stepping into the building where greats like Tina Fey and Amy Poehler began their glass-shattering careers. The Second City Theater holds comedy shows seven days a week and is a must-visit for anyone visiting or living in The Second City!


Lincoln Park

Oh, the Places we’ll go!  If you’ve ever graduated High School, you probably saw this phrase being passed around like candy at Halloween, and one of those places you could have gone was Chicago’s most desirable neighborhood, Lincoln Park.  This neighborhood is home to DePaul University and of course the city’s largest park, Lincoln Park.  Coming in at over 1,200 acres, Lincoln Park’s park, named Lincoln Park, is an oasis from the bustling city background.  Nestled in the heart of Lincoln Park (the park) is the one and only Lincoln Park Zoo which is open year-round and has free admission!  During the Holiday Season, you can even enjoy the festive lights display the zoo puts on every year called Zoo Lights. 

If you’d like to hear more about this neighborhood and possibly try one of the city’s all-time favorite sweet treats, then jump onto our signature Bikes, Bites, and Brews tour.  You’ll go for a leisurely bike ride through the park and see some of Lincoln Park’s most beautiful residential streets.

lights at Lincoln Park zoo in the Chicago neighborhood of Lincoln park

wrigley field sign and statue in the chicago neighborhood of wrigleyville


One neighborhood north and this is where we start to see a demographic shift from young established families and the business folk of downtown, to older college students and young professionals.  In short, rent starts to become more reasonable, and the nightlife district of Chicago begins in the heart of Wrigleyville.

Wrigleyville is another one of those “plus” neighborhoods, but everyone in the city of Chicago knows that this is the home of Wrigley Field and the Chicago Cubs! Taking a photo in front of the iconic stadium marquee is a must-do for sports fans across the nation.

Clark Street is lined with bars like Sluggers, a sports-themed bar that has games littering the premises and even batting cages on the second floor.  With 46 bars in the area, you’re sure to find the vibe to best suit your partying moods!

Lakeview, as the name suggests, is still a waterfront neighborhood.  You can find tennis courts, softball fields, and wild prairie nature projects along the lakefront.  This is the last neighborhood on the Northside that we visit on any of our Bobby’s Bike Hike Tours. 


Uptown is where culture meets the Mob!  Home to Little Vietnam, this is your best spot in the city for authentic Vietnamese food.  It is also home to The Green Mill; this cocktail Lounge was owned by none other than Al Capone and was run by his associate “Machine Jack” throughout prohibition.  Another classic sight in this neighborhood is the Aragon Ballroom.

Hey, quick safety tip here. Uptown is an incredible neighborhood with food, diversity, culture, and history. It can get a bit dicey after dark, however. If you’re planning on hitting the Uptown, make sure you plan your route ahead of time and don’t linger outside in areas you don’t know.  Your best bet to this area is to come early in the day when the sun is shining.


map of chicago and its surrounding area

Chicago Neighborhoods & Neighborhood Tours

With over 77 neighborhoods it can be hard to know where to start your city exploration, but hopefully, now you have an idea of what Northside neighborhoods you want to roll through.  

Here at Bobby’s Bike Hike our best tour to get to know the neighborhood’s surrounding downtown is our Neighborhoods Bike tour. Chicago is the 3rd largest city in the United States, but each neighborhood has its own identity, guaranteeing that no matter who you are, you can find a place to suit your fancy in Chi-Town.


family on a bike ride in front of lake michigan with the chicago skyline behind it

Explore Chicago’s neighborhoods with Bobby’s Bike Hike!

Book the Neighborhood Bike tour