Back to Blog
City by City

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.
WGSN Insider WGSN Insider
Chicago street art
WGSN Original Image/@tylermariemcc

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.

Chicago shops
WGSN Original Image/@tylermariemcc

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.

wrightwood 659 chicago
Wrightwood 659

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 shops
WGSN Original Image/@tylermariemcc

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.

wrightwood 659 chicago
Wrightwood 659

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

Share:
Facebook
LinkedIn