Lakeview is one of the most densely populated areas in all of Chicago. With almost 100,000 people, it has more nightlife, shopping, restaurant, and entertainment options than many mid-sized US cities. The rent rates also vary considerably, so you can find some of the highest-end stores steps away from the diviest of bars. To get the most out of the Lakeview experience a block at a time, here are the three best to get you started.
W. Diversey Ave from Clark to Orchard
At this five-corner hotspot, you can walk north up Broadway to Plato’s Closet for second-hand clothes, Rinaldi’s for a slice of NY-style pizza, and Avenue Tavern (Ave Tav), one of our favorite dive bars. North on Clark gets you to Landmark Theatres to catch an indie flick on the cheap and also brings you to both 5411 Empanadas, and La Creperie, the oldest creperie in the United States. However, one of the best blocks in Lakeview is Diversey and Clark/Broadway to Orchard Ave.
The Heart of the Fun: We think there’s an argument for all five directions this intersection takes for a top three best blocks in Lakeview spot.
On the north side of the street, you can stay at Day’s Inn, one of the three best budget hotels in the city. It’s right next door to Stan’s Donuts, some of the town’s most delicious, and right across the street from Next Door, a lovely neighborhood café. For shopping, you have AKIRA, HALO (For Men), Urban Outfitters, Express, and Trader Joe’s. The food is the best part though, with Kuma’s Too, our favorite burger joint, Half Shell, a dive bar/oyster bar, Nando’s Peri-Peri, and Matisse Tavern & Grill, a high-end pub with a huge bar menu, excellent food, and patio seating.
Side Note: “Hey, this is Lincoln Park; isn’t it?!” Well, it’s on the border of Lakeview and Lincoln Park. If you do go south down Clark, you’re in Lincoln Park, and lucky for you, it’s another one of the best neighborhoods in the city.
N. Southport Ave from Waveland to Grace
Few places in this city can boast such a well-rounded selection. For entertainment, you have the Mercury Theater for incredible live plays or musicals in an intimate venue, as well as the Music Box Theatre. Opened in 1929, it’s one of the most iconic movie houses in the country, even rumored to be haunted.
Sit down and enjoy an incredible strip or ribeye at Tango Sur (BYOB!) alongside other Argentinian fare in an intimate, high-end environment. Brunch doesn’t get any better than at Deleece, and to satisfy your sweet tooth, Candyality will blow your mind, as will Froyo Chicago, the city’s only organic frozen yogurt shop.
BYOTip: Before heading into Tango Sur, pick up a rare beer from Spencer’s Jolly Posh Foods next door to enjoy while you eat.
For high-end shopping, Que Syrah has fine wines and glassware, Baby Dolls Boutique is great for some mother-daughter time, and for trendy gifts, Southport Blooms, Edible Arrangements, and A Little Bit of This have it all.
N. Broadway from Barry to Belmont
This block is so jam-packed with excellence, it’s impossible to list all the options. In the morning, Stella’s is a casual BYOB spot for a boozy brunch, Intelligentsia has some of the finest coffee in the city, and they’re both just south of Argo Tea Café. For lunch or dinner, Casbah Café and Hatsu Hana will hit the spot, or indulge in something quick and delicious at Jersey Mike’s. Sundown is where the food gets really top-notch though, with DryHop Brewers, one of the city’s best gastropubs, serving small plate fare and house-made brews. Our favorite has to be Wilde’s Bar and Grill, a bar and restaurant with an Oscar Wilde theme complete with an enormous bar menu, outdoor seating, gourmet dishes, and their own library/reading nook.
When the sun goes down, you can keep hanging out at Wilde’s or DryHop, or check out Brendan’s Pub (a Boston sports bar), House of Hookah (a BYOB café and hookah lounge), or stroll West, North, or South to go bar hopping until closing. You’ll run into so many options it’s almost overwhelming.
Entertainment: The Laugh Factory is a world-famous venue where you can see the very best standup in Chicago, the comedy capital of the U.S.