Big Oaks is one of the smaller neighborhoods on Chicago’s far Northwest Side. It’s situated about 14 miles from the downtown Loop and is bordered to the north by Union Ridge and to the east by Jefferson Park (which is about six times the size of Big Oaks). The neighborhood abuts the lush green grounds of the Ridgemoor Country Club Golf Course to the south. Its western limit gives way to the suburb of Harwood Heights where there is a post office, restaurants, and a slew of other amenities right across the street from Big Oaks. Which is a good thing because the neighborhood itself is mostly residential with only a few pockets of commercial development and some businesses along the main thoroughfares.

As is typical of Chicago’s outlying neighborhoods, this borough is lined with rows of single-family homes that boast petite yards and detached garages you get to from a back alley. Much of the housing here was built in the 1960s and ‘70s. Some properties enjoy more ample lawn space with room for outdoor pools and abundant vegetation. Mature trees dot the landscape, giving Big Oaks an established feel that many Chicagoans look for in a place to settle down in the city. 

Architecture in this area varies from one house to the next, but you are sure to find a good showing of brick abodes, ranches, split-levels, two-story homes and even a peppering of new construction properties. Condos and other attached-unit dwellings are less common in Big Oaks however it is an option for those interested in smaller living spaces and less upkeep.

Big Oaks is roughly four blocks wide (from north to south) and 17 blocks across (east to west). So it is walkable in some ways but for commuting to downtown or other parts of the city you’ll want to hop in the car or catch a bus. Motorists can head straight north or west to get on the Kennedy Expressway (I-90). This major Chicago highway can be very backed-up during rush hour so it might be quicker to take public transportation if your destination is the Loop. The Blue Line L train has a stop at Harlem, just north of Big Oaks near the northern edge of neighboring Union Ridge. The Harlem Avenue bus will take you right there. It still takes a little time to get to the city center by public transit, but if you’re facing bumper-to-bumper traffic on the freeway as the alternative, it’s a pretty relaxing ride.