Chicago/Lakeview-North Center

Lakeview has the lion's share of Chicago's nightlife, starting with Wrigleyville, home of the Chicago Cubs and major players in the city's theater and music scenes, and Boystown, one of the largest and most vibrant LGBT communities in the United States. Down the street from both is the Belmont strip, where teen punks flock to shop and show off in the Dunkin' Donuts parking lot.

Further west are the neighborhoods of North Center, Roscoe Village and St. Ben's, which have fun, laid-back bars and restaurants.

Understand
For many years, Lakeview was so far away from the action that opening a saloon on Clark Street was considered a peaceful retirement for convicted ex-politicians in Chicago. With the expansion of the elevated train system, however, that changed rapidly, and with the 1914 construction of Weeghman Park, later to be known as Wrigley Field, Lakeview became the capital of the North Side. The Chicago Cubs, also known as the most dominant baseball franchise of the 19th century, took up residence at Wrigley and commenced the hundred-year lack of success that made them famous. Other teams have slumps, but the Cubs were beyond compare, tormenting their fans with a hundred years of near-misses, late collapses, and abject futility that is unrivaled in American professional sports. The curse finally came to an end, though: in 2016 they won their first championship in over a century. But win or lose, Game Day is always a joy in Wrigleyville. As the last franchise in baseball to install stadium lights for night games, the Cubs' schedule still features more early afternoon starts than any other team in the league, and the sun-soaked ivy walls of Wrigley Field are a pleasure no matter what the score. Today, it's a rare thing in America: a genuine neighborhood ballpark, surrounded by streets that amplify the Cubs fandom into frenzy on game day. As a nightlife destination, Wrigleyville also supports the Metro, one of Chicago's foremost rock venues, and other great ones like Schuba's, Martyrs', and The Vic. The storefront theater scene also thrives here.

But there's more to Lakeview than Wrigleyville. A short walk east is Boystown, home of a cheerful, lively LGBT community and a great destination for anyone who enjoys high-energy nightlife. It's also home to the massive annual Pride Parade in June. Roscoe Village is west of Wrigley, and is popular with older gay couples and young people lured in by fashionable boutiques and the promise of a sunny day at one of the many sidewalk cafes on Southport, not to mention Chicago's premier movie revival house, the Music Box. And Lakeview embraces its inner dive bar in North Center, full of converted warehouses, quality bowling alleys and cheap beer without the jocks.

By train
The CTA Red Line makes stops in Lakeview (Belmont) and Wrigleyville (Addison, Sheridan). The Brown Line, further west, connects with the Red Line at Belmont, and makes additional stops in Lakeview (Diversey, Wellington, Southport), Roscoe Village (Paulina), and North Center (Addison, Irving Park). All but Sheridan are wheelchair accessible. The Purple Line from the Loop and Evanston also stops at Belmont during weekday rush hours. The Union Pacific/North Line runs through Lakeview and its nearest stops are Clybourne and Ravenswood.

By bus

 * 8 Halsted travels through Boystown. A poll named this the worst bus route in the city. It's late when it shows up and goes nowhere fast.
 * 9 Ashland is an all-night route. Overnight service only runs between 95th and the North/Clark Red Line stop.
 * 22 Clark runs the length of the north side, but it slows to a crawl through Wrigleyville, particularly on weekends and on days of Cubs games. It runs all night long.
 * 36 Broadway comes in from Uptown and carries on to the Loop.
 * 49 Western runs all night through most of the city and hits the Belmont/Western intersection, near which is the best of the Roscoe Village nightlife.
 * 76 Diversey runs east/west on Diversey, the border between Lincoln Park and Lakeview, and continues to Logan Square.
 * 77 Belmont runs all night and connects Roscoe Village with the Belmont Red/Brown Line stop and Boystown.
 * 80 Irving Park runs most of the east/west length of the city, connecting with the Brown Line in North Center and the Sheridan Red Line.
 * 152 Addison travels east/west through the edge of Boystown, Wrigleyville, and on to North Center.

By car
Lake Shore Drive has an exit at Belmont. Beware of driving on Clark Street on weekends and during Cubs games, though. The taxis are a menace and the drunks are drawn to the middle of the street like flies to lights. You'll go nowhere fast and see Chicago at its worst in slow-motion.

Music
A few great venues are also listed under Drink as well.



Buy
There are a few shopping areas of note. The Southport Corridor (3300 N to 3800 N) has a row of independent boutiques along with a few specialty stores. Lincoln Avenue in Roscoe Village also has some worthwhile shops, particularly near the Paulina Brown Line stop. Clark Street near Diversey has a few chain retailers like Marshall's, and a number of upscale boutiques are crammed alongside resale behemoths on Belmont, near the train station.

On game days, the streets of Wrigleyville are packed with vendors selling cheap Cubs gear.



Eat
It's not until you reach the high-end that Lakeview dining becomes especially memorable, but there are plenty of quick, reliable places. Most importantly, a lot of them are open late — this is probably the best place in the city to grab a bite after midnight.

Mid-range




Boystown
The nightlife in Boystown may be the best in Chicago. It's wild, uninhibited and just plain fun, regardless of sexual orientation. Most of the action is on Halsted/Broadway between Addison and Belmont.



Wrigleyville
There is a watering hole for just about every personality type in Wrigleyville, particularly if you venture off the Clark Street drag near the ballpark. If you're here for a Cubs home game, rest assured that you'll be surrounded by thousands of merry Cubs fans and a world that desires nothing more than to put beer in your hands; on the downside, you'll be surrounded by thousands of Cubs fans and a world that desires nothing more than to spill beer on you, so get comfortable with sharing personal space with strangers. If you're drinking well into the night, choose wisely; as the evening wears on, a few of the bars on Clark turn into half-eaten piles of rancid nachos and the city's ripest gathering ground for date rape statistics.



Others
Lakeview bars may get a bad name from the roiling mess on Clark Street, but there are actually several great places to drink within range of Wrigley.



Sleep
Most visitors will feel comfortable staying here in terms of safety, and Lakeview is a better place to experience something of the real city than the retail isolation of the Near North. Given the boozy atmosphere, though, it's probably better for singles and young couples than families with kids in tow. (You can get to Wrigley from anywhere in the city via the Red or Brown Line, after all.)

There are also a handful of budget and mid-range options just south of Boystown in Lincoln Park. Hotels are usually booked solid for the Pride Parade in June, so make reservations early or be ready to check in other areas.

Go next

 * If it's a crosstown baseball series, you'll need to get on the Red Line and head south to Bridgeport for the Chicago White Sox.
 * It would take more than one curse to put the Cubs in their current condition, but the most famous of them, the Billy Goat Curse, began with the owner of the Billy Goat Tavern in the Near North.
 * Follow the theater trail in the storefront comedy direction to Uptown or the big-name comedy/drama direction in Old Town.
 * Andersonville is a stylish neighborhood a short trip northwest of Boystown with several gay and lesbian-friendly bars and businesses.
 * Edgewater has the LGBT Gerber/Hart Library and the less scholarly Leather Archives and Museum. During the summer, Chicago's gay community tans at Edgewater's Hollywood Beach.
 * Dedicated to original theater that explores gender and sexual identity, the About Face Theater Company performs at major theaters like Steppenwolf in Old Town and storefronts around Boystown.