Chicago: On the Ground

Insider Tour Chicago: On the Ground

Not many cities can boast being the best of both worlds. Where else can you find the beach next to the city, baseball stadiums next to museums, foodie must-haves right along artisanal cocktails? Chicago makes sure everyone is satisfied. Get swept up in the best of the Windy City’s many options with W Chicago – City Center Insider Jaclyn Costello.



1827 South Halsted St


Mr. Floyd Davis, artist and entrepreneur, divides his time between Code of Conduct (his co-owned tattoo studio) and Artpentry (his workshop). Artpentry is an independent wood shop and gallery space where he sells The Gentleman’s Boombox, an object d’art that will remix the way you play music. Choose from a collection of vintage suitcases that have been outfitted with high end speakers to make your sound system totally unique.



Millenium Park

201 E. Randolph St


Located next to the Art Institute of Chicago, this 25-acre, art-filled park is a Chicago must-see. Check out a great gathering of culture in the city with Frank Gehry’s Jay Pritzker Pavilion (in the summertime the Grant Park Orchestra performs free concerts) and Anish Kapoor’s Cloud Gate sculpture.


15 East Huron St


Chicago’s most influential fashion insider spot. Distinguished as the extended closet of Michelle Obama, the celebrated boutique has couture pieces and cult brands rare to even more renowned shopping destinations like New York and Los Angeles.



Peter Field

330 S. Wells St


The perfect custom suit is just steps away from W Chicago – City Center’s doorstep. Peter Field was founded in 2010 on the idea that if a job is worth doing, it’s worth doing right. Take a look around at the fine tailored menswear or delve into the leather accessories and bowties (if that suits your fancy).


Brooklyn Boulders

100 South Morgan St


Get out of your comfort zone with a whopping 23,000 square feet of climbing terrain located just minutes away in the West Loop. You’ll need to find your moment of zen after getting fit, so head over to the Active Collaborative Workspace that serves as a communal office and features artwork from local artists.



W Chicago – Lakeshore


True to its name, CURRENT features a fresh, modern take on seasonal Italian cuisine showcasing simple and soulful dishes alongside hand-crafted Italian cocktails, a boutique wine list, wines on tap, and an array of local micro brews. With its bold flavors and stunning backdrop (Lake Michigan and Navy Pier are just steps away), it’s an easy choice for a great Chicago meal.




W Chicago – City Center


IPO has an eclectic menu of New Urban Cuisine inspired by the diverse cultures found in Chicago. Opt for the innovative “small plates” for a decadent array of tastes, including seared scallops with chorizo, sofrito and chervil, and signature goat cheese with strawberries, mint, brown butter, corn sorbet, and fleur de sel.


Reggies Live

2105 South State St


One part rock club, one part restaurant and another part old school record store. Transformed from an auto repair shop, Reggies is now home to an ever growing music scene and has been a launching pad for alternative rock pioneers like Alkaline Trio, Gaslight Anthem, Carl Palmer, and more.



The Mid

306 N Halsted St


Headliners such A-Track, The Magician, Tiesto and more won’t pass through Chicago without a stop at The Mid. Exposed brick, hardwood floors and a stunning skyline view from its West Loop location make this club luxe yet relaxed.