The Cool Kids
Hip-hop duo The Cool Kids is comprised of Chicago native Sir Michael Rocks and Detroit native Chuck Inglish. The pair reached popularity in the mid-200s and have collaborated with everyone from Asher Roth, Mac Miller, Ludacris, Lil Wayne, Yelawolf, Drake, Kid Cudi, Travis Barker, Ghostface Killah, The Neptunes, Mayer Hawthorne, Bun B, and many others. Artists in their own right, The Cool Kids released a number of EPs and Mixtapes before taking a break in 2011. In 2016 The Cool Kids announced they were reuniting and playing select dates in 2017.
city guide:
Chicago, IL
Oak Street Beach
Located right on the shore of Lake Michigan, locals flock to Oak Street Beach for its laid-back atmosphere and unbeatable views of Chicago's skyline accented by palm trees (the city imports them every year). Play or watch a beach volleyball game and one of the many volleyball nets set up on the sand, or simply lay back and enjoy the people watching.
Oak Street Beach, Illinois, USA
Recommended by
Family Thrift Store
Large well-organized secondhand shop with three locations in Chicago, offering clothing, housewares, shoes and more. Items are hand selected for quality, cleanliness, and variety. Stop by on a Monday for their 3 for $1 Monday specials.

2160 N Milwaukee Ave, Chicago, IL 60647, USA
Recommended by
Emporium Arcade Bar
Decades of games, dozens of beers & 60-plus whiskeys in a classic tavern setting with a tin ceiling. "[At] Emporium I can play pool, air hockey, and they don't tax on drinks... I order apple juice and Hennessy." -Ajani Jones
1366 N Milwaukee Ave, Chicago, IL 60622, USA
Recommended by
Wrigley Field
Wrigley Field is a baseball park located on the North Side of Chicago, Illinois. It is the home of the Chicago Cubs, one of the city's two Major League Baseball franchises.
Chicago, IL 60613, USA
Recommended by
Union Park
Union Park spans 13.46 acres and offers tennis courts, baseball fields, a swimming pool, a playground, an athletic field for football or soccer and basketball courts, as well as a field-house with a theater. The park hosts events throughout the year including Pitchfork Music Festival, concerts, movie screenings, and more.
N Union Ave, Chicago, IL, USA
Recommended by
Jim’s Original
Old-school 24/7 hotdog stand (started in 1939) boasting the original Maxwell Street Polish sausage.
1250 S Union Ave, Chicago, IL 60607, USA
Recommended by
Giordano's has been serving its famous Chicago style deep dish pizza since 1974.
223 W Jackson Blvd, Chicago, IL 60606, USA
Recommended by
The Tonic Room
Artist-friendly lounge hosting live bands, comedians & DJs.
2447 N Halsted St, Chicago, IL 60614, USA
Recommended by
Reggies Rock Club
Reggies is a multi-purpose venue featuring a rock club, record store, rooftop deck and bar and grill housed in a former auto-bumper repair shop. Reggie's has hosted bands like the Tragically Hip, Alkaline Trio, Gaslight Anthem, The Dillinger Escape Plan, and more.
2109 S State St, Chicago, IL 60616, USA
Recommended by
Michigan Avenue
Michigan Avenue is a major north-south street in Chicago which runs at 100 east on the Chicago grid. The northern end of the street is at Lake Shore Drive on the shore of Lake Michigan in the Gold Coast Historic District. 
Chicago, IL, USA
Myopic Books
Tri-level used-books store stocking 80,000 tomes & hosting periodic concerts & poetry nights.
1564 N Milwaukee Ave, Chicago, IL 60622, USA
Millennium Park
Millennium Park is a public park located in the Loop community area of Chicago and originally intended to celebrate the third millennium. The park officially opened in 2004, four years behind schedule. Within the park is the Jay Pritzker Pavilion, Cloud Gate, the Crown Fountain, the Lurie Garden, and various other attractions including Grant Park which hosts Lollapalooza. Because the park sits atop a parking garage and the commuter rail Millennium Station, it is considered the world's largest rooftop garden.
201 E Randolph St, Chicago, IL 60601, USA
The Hideout
Prohibition-era bar in a small space that hosts all kinds of live music & dancing on Saturday night. "...they have an amazing staff and it's a beautiful venue." - Discus
1354 W Wabansia Ave, Chicago, IL 60642, USA
Rainbo Club
"It’s so Chicago to me. Cash Only, PBRs are $2, no pretense, and I always run into friends whenever I’m there. It’s like Chicago Cheers. I get whiskey, soda, bitters." — Phillip-Michael Scales
1150 N Damen Ave, Chicago, IL 60622, USA
Museum of Contemporary Art, Chicago
The Museum of Contemporary Art Chicago is located one block from the historic Water Tower in downtown Chicago. MCA features provocative and innovative contemporary art and culture exhibitions, performances, and programs. Founded in 1967, MCA is one of the world’s largest art museums.  
220 E Chicago Ave, Chicago, IL 60611, USA