Lakeview (also spelled Lake View) is the capital of Chicago’s North Side. With close to 100,000 residents, it’s the Windy City’s most populated community and one of the city’s top neighborhoods. The area is divided into Lakeview West and Lakeview East, which is considered the Greater Lakeview area. Lakeview East is home to two of the largest entertainment districts in Chicagoland—Wrigleyville, where the Cubs play, and Boystown. In addition to baseball, Wrigleyville has a thriving theater and music scene. Centered around Halsted street, Boystown was the nation’s first officially recognized gay village. Today it serves as a cultural center for one of the country’s largest LGBTQ+ communities, playing host to Chicago’s Pride Parade, a huge gay pride celebration, each June.
Upscale condos and luxury mid-rise apartments and lofts dot Lake Shore Drive and Broadway, while North Broadway and Halsted Street house small businesses, boutiques, restaurants, and more.
Commute
Located on the shore of Lake Michigan (hence the name), Lakeview is bounded by Lincoln Park to its south, Uptown to the north, Lincoln Square to the northwest, and North Center to the west.
The Chicago Transit Authority (CTA) has six L stations: Addison (Red Line), Belmont (Red, Brown, Purple Lines), Paulina (Brown Line), Sheridan (Red Line), Southport (Brown Line), and Wellington (Brown and Purple Lines). The CTA also has bus routes in the area, many with all-night routes/overnight service. Those running along North Lake Shore Drive with express services to downtown Chicago see the most action. By car, head down Lakeshore Drive to arrive downtown in about 15-20 minutes by car.
Eat
Where locals eat brunch on Sundays:
620 W Addison St
via The Flower Flat via The Flower Flat
The city is full of hole-in-the-wall greasy spoons, but we dig The Flower Flat’s homespun vibe. Chef Betsy cooks up classic comfort foods that are locally sourced when possible. The “ambiance” feels a bit like an eccentric aunt’s house, charming and cluttered with an abundance of fresh blooms, knickknacks, and mismatched furnishings.
The best coffee shop to work remotely
3800 N Clark St
Cafe by day, listening room and brewery by night, Uncommon Ground is just a hop, skip, and a jump from Wrigley. They serve organic breakfast, lunch, and dinner and host live music in the evening. Cozy up by one of the two fireplaces and feel good about patronizing the Second Greenest Restaurant in the US (the first is its other location on Devon).
The best take-out spot for when you don’t feel like cooking
1467 W Irving Park Rd
A former food truck, Roost Chicken and Biscuits serves up fried foul with a smattering of southern sides. If you don’t want to eat at one of the communal tables, you can get your chicken delivered or pick it up. Poultry plates include sandwiches, bone-in birds, tasty tenders, and “hillbilly” tacos (tenders topped with slaw and ranch on a flour tortilla). Whatever you get, order a buttermilk biscuit on the side!
Late-night eats for when you’ve had one too many
3408 N Clark St
Lakeview offers many spots to grab a bite after midnight on the weekend, but the colorful Pick Me Up Cafe on N Clark Street is open until the wee hours of the morning every night. This vegan-friendly cafe’s pizzadillas are exactly what the drunk doctor ordered.
Drink
The dive bar where everyone knows your name
3010 N Broadway
There are tons of dive bars along Broadway in Lakeview East, but Friar Tuck may have been around the longest. Established in 1970 this N Broadway dive hosts karaoke and trivia with drinks that won’t even come close to breaking the bank.
Where to drink mimosas outside
3301 North Clark Street
Located on N Clark, the rustic-chic Hutch American Bistro serves brunch daily from 10am-3pm. Grab a sidewalk seat and enjoy some Nutella dough poppers, a chicken biscuit, or some chilaquiles washed down with $16 bottomless mimosas. Thanks to those, it’s one of our favorite picks for bottomless mimosa brunch spots in Chicago.
Where to get cocktails on a first date
1349 W Cornelia Ave
Share a bottle of wine at Ella Elli. Located in the heart of Lakeview on Cornelia Avenue, you’ll find this charming spot tucked away behind the energetic Crosby’s Kitchen. It’s quiet enough so you can hold a conversation and the globally inspired menu offers plenty of small plates if you get peckish.
Things to Do
There’s nothing quite like game day in this city. In Lakeview, you’ll have easy access to Wrigley Field and the Chicago Cuba, two things you should know about before moving to Chicago. Catch a game in the summer, grab drinks at a local bar, or just take in the energy of the neighborhood on game day. In addition, Lakeview has plenty of other entertainment options.
Shops
vis Ragstock 
via Unabridged Bookstore
Krista K Boutique draws in female trendsetters with its impressive collection of upscale women’s designer clothing, shoes, jewelry, and accessories. An entire level is dedicated to denim, featuring brands from J.Brand to AG Adriano. If that’s a little too pricey, you can always shop second-hand fashion at The Brown Elephant and Ragstock.
Opened in 1980, Unabridged Bookstore is somewhat of a Lakeview institution. Knowledgeable staff member’s hand-written recommendations line the shelves of LGBTQ literature, the extensive sale section, and an award-winning children’s section.
Theaters
via Music Box Theater 
via CSz Theater 
via Greg Inda
Lakeview is home to the Belmont Theater District, which features 30 theaters and live performance venues conveniently located near the Belmont L station. Located in Roscoe Village, Chicago’s premier movie revival house, the Music Box Theatre touts itself as “Chicago’s year-round film festival”.
Annoyance Theatre serves as one of the city’s comedy training centers, showcasing improv and sketch comedy. Home to ComedySportz, the CSz Theater offers comedy six nights a week. The Playground Theater is an improviser-run comedy BYOB club where the city’s best up and coming talent perform improv, sketch and standup shows every night.
The Blue Man Group performs at Briar Street Theater. Stage 773 features drama, comedy, musicals, dance, sketch, improv and more. The Newport Theater is Wrigleyville’s hidden gem featuring artist-produced burlesque, drag, comedy, and variety shows. Stage Left Theatre has been one of the mainstays of Chicago’s storefront theater since 1982 and hosts plays that explore political and social issues. Located in the Central Lakeview area, the Vic Theatre is Chicago’s quintessential live music venue. The luxurious five-story vaudeville house has perfect acoustics and nice sightlines from the balcony.
Farmers’ Markets
The Low-Line Market offers high-quality produce, proteins, flowers, and artisanal foods from local farms and vendors on Thursday evenings at the Southport CTA Station from June through October. Open on Saturday mornings from June through September, the Lakeview Saturday Market peddles everything from fresh produce and honey to jewelry and homemade goods. Making its debut in 2019, Ward 47 Fresh Market + Artisan Fare is the new kid on the block. Located at the intersection of Marshfield and Lincoln Avenues in West Lakeview you can pick up fresh produce and take a free yoga class on Saturday mornings from June to October.
Parks
via Margaret Donahue Park Advisory Council via Margaret Donahue Park Advisory Council
There are plenty of tiny parks with playgrounds dotted throughout the Lakeview community, including Kenmore Park, Martin (Johnny) Park, Lois Klein Park, Juniper Park, Merryman Park, South Lakeview Park, Kelly (John) Park, Sheil (Bernard) Community Center Park, Donahue (Margaret) Park, Evergreen Park, and Wendt (Kenneth) Park. At 2.41 acres Gill (Joseph) Park is the area’s largest and features a fieldhouse that contains a fitness center, indoor swimming pool, gymnasium, assembly hall, and more.
Top-Rated Neighborhood Places
Housed in an old Schlitz brewery, Schubas is Lakeview’s intimate, low-key music venue that hosts a wide range of live acts, from indie to jazz. Located on N Clark St across from Uptown’s magnificent Graceland Cemetery, Wunders Cemetery features some intriguing monuments dating back to 1859.
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