Visit The Windy City with our latest Chicago city guide

Discover the best of Chicago’s thriving community-focused fashion, retail and culture scene, handpicked by our local expert, Tyler McClelland.

Chicago is a city of distinct neighbourhoods, with a retail culture that reflects its heritage and artistic innovation. Renowned for its taste-making streetwear scene, architectural innovations and multicultural food offerings, the ‘Windy City’ offers visitors a plethora of inspiring activities.

From streetwear to considered formal wardrobes, Chicago's shops cater to everyone

Multi-brand shops create a community-focused retail culture by featuring local designers and artist collaborations. Visit RSVP Gallery, a conceptual retail experience co-founded by the late designer Virgil Abloh and Don Crawley that has remained a Chicago staple at the intersection of luxury streetwear and pop culture; or explore Ikram, a woman-owned boutique led by Michelle Obama’s wardrobe advisor, Ikram Goldman. 

For community-focused shops that feature contemporary furniture and locally made products, visit Mashallah for timeless jewellery, home decor and spiritual products, or The Silver Room, a showroom that introduces customers to unique goods, sounds and events centring Black creators and narratives.

The multicultural city has every cuisine you can think of

Chicago’s food scene offers a dynamic mix of innovative culinary trends and traditional favourites, making it a haven for foodies. Visit JIAO by Qing Xiang Yuan Dumplings, a casual spin-off to QXY located in Chicago’s famous Chinatown, known for its rotating menu, handmade dumplings and authentic Chinese ingredients.

The Violet Hour’s mysterious candlelit bar values high-quality and seasonally driven cocktails, and is known as a pioneer of Chicago’s craft cocktail movement. Alternatively, visit the humble Dusek’s Tavern, located inside the iconic music venue Thalia Hall and is centred around American food with a Parisian flare.

Chicago's at the fore of contemporary art

Rich with artistic expression, Chicago’s cultural scene is vibrant, diverse and caters to a wide range of interests. Visit Wrightwood 659, a contemplative space designed to encourage thoughtful engagement with art and architecture by Pritzker Prize-winning architect Tadao Ando, or The Renaissance Society, located on the University of Chicago campus. This century-old museum connects its audience to the expansive landscape of contemporary art through its commitment to fostering engagement with new ideas in arts and culture.

If you’re a WGSN subscriber, get inspired by our Chicago: Inspiration City report.  Live now on the site.