Lakeview

Don’t let the name fool you, as it borderlines on misnomer. You can get a view the lake from this neighborhood, but you may need to get up on a rooftop by Wrigley Field to see it. Not to worry though, the people watching at ground level is nearly as hypnotic as the waves rolling in from Lake Michigan. And, wow! There’s a lot going on.

If someone were to create a Venn Diagram that laid out every neighborhood on the North Side of Chicago, overlapping but distinct, in the center of it all would be Lakeview. Within a few minutes of walking you can go from eating and drinking, to shopping and thrifting, laughing and dancing, and—of course—even root, root, rooting. Though that last part is distinct to Lakeview, as Wrigleyville is actually a neighborhood within a neighborhood.

Look just past the façade and you’ll quickly find world-class theatre, comedy, and music happening nightly. But, don’t just be a spectator! Nightclubs and world-renowned DJs are bumping and spinning well into the wee hours on a regular basis. Before you head out for the night, though, consider any one of a huge number of boutiques and retail stores in the neighborhood to get yourself pulled together.

Dining and entertainment aren’t the only ways to spend your discretionary income in Lakeview. Take a walk up and down the Southport Corridor and you’ll find a variety of independent and big-name stores, services, and historic gems like the Music Box Theatre—which was built back when “talkies” were the latest technology. With everything on offer, it’s easy to forget Lakeview is very much a family-friendly neighborhood and has excellent options when it comes to choosing schools for the kiddos.

Another thing about Lakeview (so many things!), is when you step off any of the main drags and get a block or so away from the party, you find yourself in serene tree-lined streets with houses ranging from very vintage to very contemporary. There is also a great sense of community and diversity in Lakeview as it is also home to the North Halsted neighborhood which was the first officially recognized LGBTQ+ village in the country.

Being the unofficial hub of the North Side means the transportation options are many. The CTA has a full six “L” stops on three different lines to choose from, not to mention the slew of buses, taxis, rental bikes and scooters and on and on. Plus, Lake Shore Drive is right there; you just can’t really see it unless…ah, you know.